the chemistry of fragrances...the chemistry of fragrances perfumes and more 28 march 2019 1. brief...
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The Chemistry of FragrancesPerfumes and More
28 March 2019
The Chemistry of FragrancesPerfumes and More
28 March 2019
1. Brief History
The Chemistry of FragrancesPerfumes and More
28 March 2019
1. Brief History2. Nobel Prize (2004)
The Chemistry of FragrancesPerfumes and More
28 March 2019
1. Brief History2. Nobel Prize (2004)3. Catalytic Preparation of Fragrances
The Chemistry of FragrancesPerfumes and More
28 March 2019
1. Brief History2. Nobel Prize (2004)3. Catalytic Preparation of Fragrances4. Industrial Organometallic Processes
The Chemistry of FragrancesPerfumes and More
28 March 2019
1. Brief History2. Nobel Prize (2004)3. Catalytic Preparation of Fragrances4. Industrial Organometallic Processes5. Toxicology Outline
The Chemistry of FragrancesPerfumes and More
28 March 2019
1. Brief History2. Nobel Prize (2004)3. Catalytic Preparation of Fragrances4. Industrial Organometallic Processes5. Toxicology Outline6. Review of Flavor & Fragrance (2018)
Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
Brief History of Fragrances
• <1850: only the wealthiest could afford fragrances and perfumes
• <1900: Perfumes were made of entirely natural materials
• 2019: over 3000 fragrance ingredients are available to consumers (>90% chemically synthesized)
• Expected in everything from household cleaners to shampoo to processed food and more!
Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
Brief History of Fragrances
• Use of fragranced materials dates back thousands of years
• “Perfume” comes from Latin per fume meaning “through smoke” as in the burning of incense
• Egyptians pressed, boiled, dried, powdered, macerated in fat, and even distilled
• The early Crusades spread perfumes to Middle Age Europe
• Alchemy turned into chemistry in the 19th century, and fragrance was at the forefront
• 1882: Paul Parquet created Fougere Royale from synthetic coumarin, oakmoss, geranium, and bergamont
Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
Brief History of Fragrances
• Traditional discovery and development of new synthetic chemicals were based on the analysis of natural sources:• Plants (lavender, jasmine)• Fruits (lemon, orange)• Animal (musk, ambergris)
• Three main methods for acquiring
Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
Brief History of Fragrances
• Traditional discovery and development of new synthetic chemicals were based on the analysis of natural sources:• Plants (lavender, jasmine)• Fruits (lemon, orange)• Animal (musk, ambergris)
• Three main methods for acquiring
Expression
Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
Brief History of Fragrances
• Traditional discovery and development of new synthetic chemicals were based on the analysis of natural sources:• Plants (lavender, jasmine)• Fruits (lemon, orange)• Animal (musk, ambergris)
• Three main methods for acquiring
Steam Distillation
Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
Brief History of Fragrances
• Traditional discovery and development of new synthetic chemicals were based on the analysis of natural sources:• Plants (lavender, jasmine)• Fruits (lemon, orange)• Animal (musk, ambergris)
• Three main methods for acquiring
Solvent Extraction
Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
Brief History of Fragrances
• Chanel No5 was the first commercial perfume to use synthetic materials
• Synthetic materials are:• Cheaper• Less prone to degradation
Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
Brief History of Fragrances
• Much like medicinal chemistry, derivatives are explored after natural detection
Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
Development of Types of Odors
Musk
Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
Development of Types of Odors
Woody
Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
Development of Types of Odors
‘Prodrug’ equivalence in perfumes
Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
Development of Types of Odors
Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
Development of Types of Odors
.
2004 Nobel Prize in Medicine & Physiology
Linda B. Buck Richard Axel
Howard Hughes Medical Institute Columbia University College of Physicians and Surgeons
Howard Hughes Medical Institute Fred Hutchinson Cancer Research Center
Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
2004 Nobel Prize in Medicine & Physiology
Two main questions:• How do mammals detect so many different environmental chemicals?• How does the brain translate those chemicals into diverse odor
perception and behaviors?
Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
2004 Nobel Prize in Medicine & Physiology
Two main questions:• How do mammals detect so many different environmental chemicals?• How does the brain translate those chemicals into diverse odor
perception and behaviors?
Humans can sense 10,000 to 100,000 chemicals (small, volatile)
Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
2004 Nobel Prize in Medicine & Physiology
Two main questions:• How do mammals detect so many different environmental chemicals?• How does the brain translate those chemicals into diverse odor
perception and behaviors?
Humans can sense 10,000 to 100,000 chemicals (small, volatile)
G-protein coupled receptors (GPCR) were discovered to be responsible for odor detection
Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
2004 Nobel Prize in Medicine & Physiology
Two main questions:• How do mammals detect so many different environmental chemicals?• How does the brain translate those chemicals into diverse odor
perception and behaviors?
Humans can sense 10,000 to 100,000 chemicals (small, volatile)
G-protein coupled receptors (GPCR) were discovered to be responsible for odor detection
Odor receptors seem to be randomly distributed
Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
2004 Nobel Prize in Medicine & Physiology
Two main questions:• How do mammals detect so many different environmental chemicals?• How does the brain translate those chemicals into diverse odor
perception and behaviors?
Humans can sense 10,000 to 100,000 chemicals (small, volatile)
G-protein coupled receptors (GPCR) were discovered to be responsible for odor detection
Odor receptors seem to be randomly distributed
Different odorants can all trigger one type ofreceptor neuron
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?It’s a primal sense
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?It’s a primal sense
Can we study smell?
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?It’s a primal sense
Can we study smell?It’s difficult to understand, but ithas tangible pieces(molecules &receptors)
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?It’s a primal sense
Can we study smell?It’s difficult to understand, but ithas tangible pieces(molecules &receptors)
What questionsshould be asked?
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?It’s a primal sense
Can we study smell?It’s difficult to understand, but ithas tangible pieces(molecules &receptors)
What questionsshould be asked?
How do we smell?How does the brain learnand interpret these signals?
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?It’s a primal sense
Can we study smell?It’s difficult to understand, but ithas tangible pieces(molecules &receptors)
What questionsshould be asked?
How do we smell?How does the brain learnand interpret these signals?
• 1300 odor receptors in a mouse
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?It’s a primal sense
Can we study smell?It’s difficult to understand, but ithas tangible pieces(molecules &receptors)
What questionsshould be asked?
How do we smell?How does the brain learnand interpret these signals?
• 1300 odor receptors in a mouse• 500 in a human
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?It’s a primal sense
Can we study smell?It’s difficult to understand, but ithas tangible pieces(molecules &receptors)
What questionsshould be asked?
How do we smell?How does the brain learnand interpret these signals?
• 1300 odor receptors in a mouse• 500 in a human
• C. elegans have 302 neurons of which 16
are dedicated to odorrepresenting a 1000
odorant receptorgenes
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & Physiology
Why study smell?It’s a primal sense
Can we study smell?It’s difficult to understand, but ithas tangible pieces(molecules &receptors)
What questionsshould be asked?
How do we smell?How does the brain learnand interpret these signals?
• 1300 odor receptors in a mouse• 500 in a human
• C. elegans have 302 neurons of which 16
are dedicated to odorrepresenting a 1000
odorant receptorgenes
Gene coding isclearly important
for odorrecognition
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & PhysiologyMapping brains/neurons when exposed to odors in mice & fruit flies
Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
2004 Nobel Prize in Medicine & PhysiologyMapping brains/neurons when exposed to odors in mice & fruit flies
Clear relationship but get stuck at “ghost in the machine”
Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
Catalytic Preparation of FragrancesCatalytic Hydrogenations
Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
Catalytic Preparation of Fragrances
Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
Catalytic Preparation of FragrancesCatalytic Hydride Reduction
Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
Catalytic Preparation of FragrancesCatalytic Dehydrogenation
Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
Catalytic Preparation of FragrancesCatalytic C–C bond formation
Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
Catalytic Preparation of FragrancesCatalytic C–O bond formation/cleavage
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Synthesis of Fragrances with Organometallic ChemistryAldehydes are extremely common in synthetic perfumes
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Synthesis of Fragrances with Organometallic ChemistryAldehydes are extremely common in synthetic perfumes
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Aldehydes are extremely common in synthetic perfumes
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Aldehydes are extremely common in synthetic perfumes
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Aldehydes are extremely common in synthetic perfumes
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.Bovo, S.; Scrivanti, A.; Bertoldini, M.; Beghetto, V.; Matteoli, U., A New Enantioselective Catalytic Route to Florhydral®. Synthesis 2008, 16, 2547–2550.
Aldehydes are extremely common in synthetic perfumes
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Aldehydes are extremely common in synthetic perfumes
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Aldehydes are extremely common in synthetic perfumes
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.da Silva, J. G.; Vieira, C. G.; dos Santos, E. N.; Gusevskaya, E. V., Hydroformylation of endocyclic double bonds in para-menthenic terpenes under mild conditions. Applied Catalysis A: General 2009, 365 (2), 231-236.
Aldehydes are extremely common in synthetic perfumes
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.da Silva, J. G.; Vieira, C. G.; dos Santos, E. N.; Gusevskaya, E. V., Hydroformylation of endocyclic double bonds in para-menthenic terpenes under mild conditions. Applied Catalysis A: General 2009, 365 (2), 231-236.
Aldehydes are extremely common in synthetic perfumes
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Aldehydes are extremely common in synthetic perfumes
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Hydrogenation with Ruthenium Yields Synthetic Analogs
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.Christian C, Gautier A, Blanc P-A (1995) Eur. Pat. Appl. EP 643958 A2 (Firmenich SA)
Hydrogenation with Ruthenium Yields Synthetic Analogs
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.Chapuis C (2004) Chem Biodivers 1:980-102
Hydrogenation with Ruthenium Yields Synthetic Analogs
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
Hydrogenation with Ruthenium Yields Synthetic Analogs
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
Hydrogenation with Ruthenium Yields Synthetic Analogs
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
Hydrogenation with Ruthenium Yields Synthetic Analogs
Synthesis of Fragrances with Organometallic Chemistry
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
Criteria 2 Document
Toxicology
©2019 Research Institute for Fragrance Materials
Toxicology
©2019 Research Institute for Fragrance Materials
Toxicology
©2019 Research Institute for Fragrance Materials
#3
Exposure
Threshold
#4
Data
Generation
#2
Read-
Across Data
#1
Data
Methods
Toxicology
©2019 Research Institute for Fragrance Materials
How to analyze 3000 fragrance materials?
Toxicology
©2019 Research Institute for Fragrance Materials
Fragrances
Acids Alcohols Esters Aldehydes KetonesNitrogen
containingOxygen
containingSulfur
containingHydrocarbons
UnsaturatedSaturated
Vinyl Vinylene Aromatic a,b unsaturated Heterocyclic
ConjugatedCyclic Straight chain Branched
Spiro Bicyclo Macrocyclic
Cyclic Straight chain Branched
# C, LogKow # C, LogKow
Clustering based on extended fragment
Extended fragment
Functional group
Clustering based on functional group
Toxicology
©2019 Research Institute for Fragrance Materials
How to analyze 3000 fragrance materials?
Toxicology
©2019 Research Institute for Fragrance Materials
Alpha alkylsubstituted
Alpha aryl substituted
Hetero aromatic
Alkyl substituted aromaticBeta alkyl
substituted
Alpha alkyl substituted
hetero aromatic
Rea
ctiv
ity
Similar
Dissimilar
Cinnamaldehyde
o-MethoxyCinnamaldehyde
p-MethoxyCinnamaldehyde
Toxicology
©2019 Research Institute for Fragrance Materials
http://fragrancematerialsafetyresource.elsevier.com
©2019 Research Institute for Fragrance Materials
.
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Anesthetic and fear
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Tsutsui, Y.; Mizuno, J.; Sunada, K., Does the aroma of a patient’s preferred dental topical anaesthetic affect anxiety,
fear, and autonomic nervous system activity prior to dental local anaesthesia? A randomized trial. Flavour Fragrance
J. 2018, 33 (6), 405-410.
Hamakawa, M.; Okamoto, T., The effect of different emotional states on olfactory perception: A preliminary study. Flavour
Fragrance J. 2018, 33 (6), 420-427.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Tsutsui, Y.; Mizuno, J.; Sunada, K., Does the aroma of a patient’s preferred dental topical anaesthetic affect anxiety, fear, and
autonomic nervous system activity prior to dental local anaesthesia? A randomized trial. Flavour Fragrance J. 2018, 33 (6),
405-410.
Hamakawa, M.; Okamoto, T., The effect of different emotional states on olfactory perception: A preliminary study.
Flavour Fragrance J. 2018, 33 (6), 420-427.
Emotional states
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Lee, S. M.; Cho, A. R.; Yoo, S.-H.; Kim, Y.-S., Effects of maltodextrins with different dextrose-equivalent values. Flavour
Fragrance J. 2018, 33 (2), 153-159.
Apriceno, A.; Girelli, A. M.; Scuto, F. R.; Tarola, A. M., Determination of furanic compounds and acidity for Italian honey quality.
Flavour Fragrance J. 2018, 33 (6), 411-419.
Texier–Bonniot, T.; Berdagué, P.; Robins, R. J.; Remaud, G.; Lesot, P., Analytical contribution of deuterium 2D-NMR in oriented media
to 2H/1H isotopic characterization: the case of vanillin. Flavour Fragrance J. 2018, 33 (3), 217-229.
Analyzing biodegradation
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Lee, S. M.; Cho, A. R.; Yoo, S.-H.; Kim, Y.-S., Effects of maltodextrins with different dextrose-equivalent values. Flavour Fragrance J.
2018, 33 (2), 153-159.
Apriceno, A.; Girelli, A. M.; Scuto, F. R.; Tarola, A. M., Determination of furanic compounds and acidity for Italian honey
quality. Flavour Fragrance J. 2018, 33 (6), 411-419.
Texier–Bonniot, T.; Berdagué, P.; Robins, R. J.; Remaud, G.; Lesot, P., Analytical contribution of deuterium 2D-NMR in oriented media
to 2H/1H isotopic characterization: the case of vanillin. Flavour Fragrance J. 2018, 33 (3), 217-229.
Quality testing
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Lee, S. M.; Cho, A. R.; Yoo, S.-H.; Kim, Y.-S., Effects of maltodextrins with different dextrose-equivalent values. Flavour Fragrance J.
2018, 33 (2), 153-159.
Apriceno, A.; Girelli, A. M.; Scuto, F. R.; Tarola, A. M., Determination of furanic compounds and acidity for Italian honey quality.
Flavour Fragrance J. 2018, 33 (6), 411-419.
Texier–Bonniot, T.; Berdagué, P.; Robins, R. J.; Remaud, G.; Lesot, P., Analytical contribution of deuterium 2D-NMR in
oriented media to 2H/1H isotopic characterization: the case of vanillin. Flavour Fragrance J. 2018, 33 (3), 217-229.
2D-NMR probing technique
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Taiti, C.; Costa, C.; Figorilli, S.; Billi, M.; Caparrotta, S.; Comparini, D.; Mancuso, S., Volatome analysis approach for the
taxonomic classification of tree exudate collection using Proton Transfer Reaction Time of Flight Mass Spectrometry. Flavour
Fragrance J. 2018, 33 (3), 245-262.
Belhassen, E.; Bressanello, D.; Merle, P.; Raynaud, E.; Bicchi, C.; Chaintreau, A.; Cordero, C., Routine quantification of 54 allergens in
fragrances using comprehensive two-dimensional gas chromatography-quadrupole mass spectrometry with dual parallel secondary
columns. Part I: Method development. Flavour Fragrance J. 2018, 33 (1), 63-74.
Plant classification technique
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Taiti, C.; Costa, C.; Figorilli, S.; Billi, M.; Caparrotta, S.; Comparini, D.; Mancuso, S., Volatome analysis approach for the taxonomic
classification of tree exudate collection using Proton Transfer Reaction Time of Flight Mass Spectrometry. Flavour Fragrance J. 2018,
33 (3), 245-262.
Belhassen, E.; Bressanello, D.; Merle, P.; Raynaud, E.; Bicchi, C.; Chaintreau, A.; Cordero, C., Routine quantification of 54
allergens in fragrances using comprehensive two-dimensional gas chromatography-quadrupole mass spectrometry with dual
parallel secondary columns. Part I: Method development. Flavour Fragrance J. 2018, 33 (1), 63-74.
Allergen detection
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Jentzsch, P. V.; Gualpa, F.; Ramos, L. A.; Ciobotă, V., Adulteration of clove essential oil: Detection using a handheld Raman
spectrometer. Flavour Fragrance J. 2018, 33 (2), 184-190.
Purity testing
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Trytek, M.; Paduch, R.; Pięt, M.; Kozieł, A.; Kandefer-Szerszeń, M.; Szajnecki, Ł.; Gromada, A., Biological activity of
oxygenated pinene derivatives on human colon normal and carcinoma cells. Flavour Fragrance J. 2018, 33 (6), 428-437.
Nagai, K.; Horii, Y.; Fujisaki, Y.; Fuyuki, R.; Misonou, Y., Effects of olfactory stimulation with scents of grapefruit and
lavender essential oils on the skeletal muscle sympathetic nerve and muscle blood flow in rats. Flavour Fragrance J. 2018,
33 (2), 135-143.
Satou, T.; Hayakawa, M.; Goto, Y.; Masuo, Y.; Koike, K., Anxiolytic-like effects of essential oil from Thymus vulgaris was
increased during stress. Flavour Fragrance J. 2018, 33 (2), 191-195.
Cancer treatment
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Trytek, M.; Paduch, R.; Pięt, M.; Kozieł, A.; Kandefer-Szerszeń, M.; Szajnecki, Ł.; Gromada, A., Biological activity of
oxygenated pinene derivatives on human colon normal and carcinoma cells. Flavour Fragrance J. 2018, 33 (6), 428-437.
Nagai, K.; Horii, Y.; Fujisaki, Y.; Fuyuki, R.; Misonou, Y., Effects of olfactory stimulation with scents of grapefruit and
lavender essential oils on the skeletal muscle sympathetic nerve and muscle blood flow in rats. Flavour Fragrance J. 2018, 33 (2),
135-143.
Satou, T.; Hayakawa, M.; Goto, Y.; Masuo, Y.; Koike, K., Anxiolytic-like effects of essential oil from Thymus vulgaris was
increased during stress. Flavour Fragrance J. 2018, 33 (2), 191-195.
Blood flow
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Trytek, M.; Paduch, R.; Pięt, M.; Kozieł, A.; Kandefer-Szerszeń, M.; Szajnecki, Ł.; Gromada, A., Biological activity of
oxygenated pinene derivatives on human colon normal and carcinoma cells. Flavour Fragrance J. 2018, 33 (6), 428-437.
Nagai, K.; Horii, Y.; Fujisaki, Y.; Fuyuki, R.; Misonou, Y., Effects of olfactory stimulation with scents of grapefruit and
lavender essential oils on the skeletal muscle sympathetic nerve and muscle blood flow in rats. Flavour Fragrance J. 2018,
33 (2), 135-143.
Satou, T.; Hayakawa, M.; Goto, Y.; Masuo, Y.; Koike, K., Anxiolytic-like effects of essential oil from Thymus vulgaris
was increased during stress. Flavour Fragrance J. 2018, 33 (2), 191-195.
Stress reduction
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Satou, T.; Hanashima, Y.; Mizutani, I.; Koike, K., The effect of inhalation of essential oil from Rosmarinus officinalis
on scopolamine-induced Alzheimer's type dementia model mice. Flavour Fragrance J. 2018, 33 (3), 230-234.
Ambrosch, S.; Duliban, C.; Heger, H.; Moser, E.; Laistler, E.; Windischberger, C.; Heuberger, E., Effects of 1,8-Cineole and
(–)-Linalool on Functional Brain Activation in a Working Memory Task. Flavour Fragrance J. 2018, 33 (3), 235-244.
Natsch, A.; Kern, S.; Corbi, E.; Pérès, C.; Nägelin, M.; Leijs, H.; van Strien, M.; Calandra, M. J.; Wang, Y., Interlaboratory
evaluation of methods to quantify skin-sensitizing hydroperoxides of limonene and linalool (II): Analysis in cosmetic bases.
Flavour Fragrance J. 2018, 33 (4), 322-330.
Alzheimer’s treatment
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Satou, T.; Hanashima, Y.; Mizutani, I.; Koike, K., The effect of inhalation of essential oil from Rosmarinus officinalis on
scopolamine-induced Alzheimer's type dementia model mice. Flavour Fragrance J. 2018, 33 (3), 230-234.
Ambrosch, S.; Duliban, C.; Heger, H.; Moser, E.; Laistler, E.; Windischberger, C.; Heuberger, E., Effects of 1,8-Cineole and (–)-
Linalool on Functional Brain Activation in a Working Memory Task. Flavour Fragrance J. 2018, 33 (3), 235-244.
Natsch, A.; Kern, S.; Corbi, E.; Pérès, C.; Nägelin, M.; Leijs, H.; van Strien, M.; Calandra, M. J.; Wang, Y., Interlaboratory
evaluation of methods to quantify skin-sensitizing hydroperoxides of limonene and linalool (II): Analysis in cosmetic bases.
Flavour Fragrance J. 2018, 33 (4), 322-330.
Brain activity
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Satou, T.; Hanashima, Y.; Mizutani, I.; Koike, K., The effect of inhalation of essential oil from Rosmarinus officinalis on
scopolamine-induced Alzheimer's type dementia model mice. Flavour Fragrance J. 2018, 33 (3), 230-234.
Ambrosch, S.; Duliban, C.; Heger, H.; Moser, E.; Laistler, E.; Windischberger, C.; Heuberger, E., Effects of 1,8-Cineole and
(–)-Linalool on Functional Brain Activation in a Working Memory Task. Flavour Fragrance J. 2018, 33 (3), 235-244.
Natsch, A.; Kern, S.; Corbi, E.; Pérès, C.; Nägelin, M.; Leijs, H.; van Strien, M.; Calandra, M. J.; Wang, Y.,
Interlaboratory evaluation of methods to quantify skin-sensitizing hydroperoxides of limonene and linalool (II):
Analysis in cosmetic bases. Flavour Fragrance J. 2018, 33 (4), 322-330.
Cosmetic damages
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Swathy, J. S.; Mishra, P.; Thomas, J.; Mukherjee, A.; Chandrasekaran, N., Nanometric neem oil emulsification
through microfluidization, and its therapeutic potential against Aeromonas culicicola infection in Cyprinus carpio.
Flavour Fragrance J. 2018, 33 (5), 340-350.
Antibacterial effects
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Yi, Q.-y.; Yi, S.-w.; Qin, T.-f.; Li, C.-y., Using RAPD and ISSR Molecular Markers to Analyze the Genetic Diversity of
Rose scented Pelargonium Populations. Flavour Fragrance J. 2018, 33 (1), 75-81.
Genetic testing
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Starkenmann, C.; Niclass, Y.; Beaussoubre, P.; Zimmermann, J.; Cayeux, I.; Chappuis, C. J.-F.; Fieber, W., Use of
fecal and sawdust biochar as a new perfume delivery system. Flavour Fragrance J. 2018, 33 (1), 82-90.
Song, J.; Chen, H., Preparation of aroma microcapsules with sodium alginate and tetradecylallyldimethylammonium
bromide (TADAB) and its potential applications in cosmetics. Flavour Fragrance J. 2018, 33 (2), 160-165.
Fecal & Sawdust biochar for perfume delivery
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Starkenmann, C.; Niclass, Y.; Beaussoubre, P.; Zimmermann, J.; Cayeux, I.; Chappuis, C. J.-F.; Fieber, W., Use of fecal and
sawdust biochar as a new perfume delivery system. Flavour Fragrance J. 2018, 33 (1), 82-90.
Song, J.; Chen, H., Preparation of aroma microcapsules with sodium alginate and tetradecylallyldimethylammonium
bromide (TADAB) and its potential applications in cosmetics. Flavour Fragrance J. 2018, 33 (2), 160-165.
Alginate microcapsules
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Mohammadi, N.; Ehsani, M. R.; Bakhoda, H., Development of caffeine-encapsulated alginate-based matrix combined
with different natural biopolymers, and evaluation of release in simulated mouth conditions. Flavour Fragrance J.
2018, 33 (5), 357-366.
Horváth, B.; Pál, S.; Széchenyi, A., Preparation and in vitro diffusion study of essential oil Pickering emulsions stabilized by
silica nanoparticles. Flavour Fragrance J. 2018, 33 (6), 385-396.
Alginate encapsulation
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Mohammadi, N.; Ehsani, M. R.; Bakhoda, H., Development of caffeine-encapsulated alginate-based matrix combined with
different natural biopolymers, and evaluation of release in simulated mouth conditions. Flavour Fragrance J. 2018, 33 (5),
357-366.
Horváth, B.; Pál, S.; Széchenyi, A., Preparation and in vitro diffusion study of essential oil Pickering emulsions
stabilized by silica nanoparticles. Flavour Fragrance J. 2018, 33 (6), 385-396.
Nanoparticle stabilization
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems*• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Chappuis, C. J.-F.; Huber, R.; Niclass, Y.; Starkenmann, C., Simulating latrine conditions to assess perfume
performance against malodour. Flavour Fragrance J. 2018, 33 (4), 313-321.
Latrine models
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Romagny, S.; Coureaud, G.; Thomas-Danguin, T., Key odorants or key associations? Insights into elemental and
configural odour processing. Flavour Fragrance J. 2018, 33 (1), 97-105.
Bastiaan-Net, S.; van den Berg-Somhorst, D. B. P. M.; Ariëns, R. M. C.; Paques, M.; Mes, J. J., A novel functional screening
assay to monitor sweet taste receptor activation in vitro. Flavour Fragrance J. 2018, 33 (2), 173-183.
Odor and mental connections
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Romagny, S.; Coureaud, G.; Thomas-Danguin, T., Key odorants or key associations? Insights into elemental and configural
odour processing. Flavour Fragrance J. 2018, 33 (1), 97-105.
Bastiaan-Net, S.; van den Berg-Somhorst, D. B. P. M.; Ariëns, R. M. C.; Paques, M.; Mes, J. J., A novel functional
screening assay to monitor sweet taste receptor activation in vitro. Flavour Fragrance J. 2018, 33 (2), 173-183.
Monitoring sweet receptors
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Cicchetti, E.; Vasseur, C., Critical comparison of selected olfactometric methods for the determination of impact
odorants. Proposal of a new representation of olfactometric results. Flavour Fragrance J. 2018, 33 (2), 144-152.
Argument for bubble plots
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Larcinese-Hafner, V.; Tchakalova, V., Co-surfactant, co-solvent, and hydrotropic properties of some common cooling
agents. Flavour Fragrance J. 2018, 33 (4), 303-312.
Barzegar, H.; Mehrnia, M. A.; Nasehi, B.; Alipour, M., Fabrication of peppermint essential oil nanoemulsions by
spontaneous method: Effect of preparing conditions on droplet size. Flavour Fragrance J. 2018, 33 (5), 351-356.
Surfactant properties of cooling agents
.
• Emotional Response• Analytical Testing• Medicinal Testing• Botany• Flavor/Scent Delivery Systems• Physical Response (biology)• Categorization Methods for Data• Physical Properties
Some Topics Not Covered
Larcinese-Hafner, V.; Tchakalova, V., Co-surfactant, co-solvent, and hydrotropic properties of some common cooling agents.
Flavour Fragrance J. 2018, 33 (4), 303-312.
Barzegar, H.; Mehrnia, M. A.; Nasehi, B.; Alipour, M., Fabrication of peppermint essential oil nanoemulsions by
spontaneous method: Effect of preparing conditions on droplet size. Flavour Fragrance J. 2018, 33 (5), 351-356.
Nanoemulsions
Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172.
Enantioselective Syntheses and Sensory Properties of 2-Alken-4-olides
Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172..
Enantioselective Syntheses and Sensory Properties of 2-Alken-4-olides
Sharplessasymmetricdihydroxylation
Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172..
Enantioselective Syntheses and Sensory Properties of 2-Alken-4-olides
Sensory panel test:5 healthy, non-smoking judges
2 male, 3 femaleAges 23 to 29
Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172..
Enantioselective Syntheses and Sensory Properties of 2-Alken-4-olides
Sensory panel test:5 healthy, non-smoking judges
2 male, 3 femaleAges 23 to 29
Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172..
Enantioselective Syntheses and Sensory Properties of 2-Alken-4-olides
Sensory panel test:5 healthy, non-smoking judges
2 male, 3 femaleAges 23 to 29
Retention Times
Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172..
Enantioselective Syntheses and Sensory Properties of 2-Alken-4-olides
Sensory panel test:5 healthy, non-smoking judges
2 male, 3 femaleAges 23 to 29
Amount neededfor detection
Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links
between odorants and odors
• Break up odors into “subjective” categories• 150 odor notes• 1000-2000 odorants
• Use self-organizing maps (SOMs) to relate odor with structure via Artificial Neural Network (ANN)
• Draw 3777 odorants from Flavor-Base (a large library of compounds)
• Retain 3571 after removing compounds activating retronasal stimuli
• Remove any descriptors with <5 related compounds• Kept ones like “fruity,” “floral”• Removed 63 odorants
• Used AI to split odorants into similarity “trees”; cut trees at 3 dimensions deep
Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links
between odorants and odors
Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links
between odorants and odors
“Green Split”
Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links
between odorants and odors
Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links
between odorants and odors
Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links
between odorants and odors
• “Rose” can be related to “honey,” “metallic,” “geranium”• “Honey” and “geranium” never exist in an odor description
together• “Rose-honey” and “rose-geranium-metallic” are different
odors related to the perception of the flowers called “roses”
Ding, R.; Li, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Synthesis of butenolides by reactions of 3-alkenoic acids with diphenyl sulfoxide/oxalyl chloride. Flavour Fragrance J. 2018, 33 (6), 397-404.Stamatopoulos, P.; Frérot, E.; Tempère, S.; Pons, A.; Darriet, P., Identification of a New Lactone Contributing to Overripe Orange Aroma in Bordeaux Dessert Wines via Perceptual InteractionPhenomena. J. Agric. Food. Chem. 2014, 62 (12), 2469-2478.Rajkumar, G.; Shanmugam, S.; Galvâo, M. d. S.; Dutra Sandes, R. D.; Leite Neta, M. T. S.; Narain, N.; Mujumdar, A. S., Comparative evaluation of physical properties and volatiles profile of cabbages subjected to hot air and freeze drying. LWT 2017, 80, 501-509.Shu, N.; Shen, H., Aroma‐impact compounds in Lysimachia foenum‐graecum extracts. Flavour Fragrance J. 2009, 24 (1), 1-6.
Synthesis of butenolides by reactions of 3‐alkenoic acids with diphenyl sulfoxide/oxalyl chloride
Ding, R.; Li, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Synthesis of butenolides by reactions of 3-alkenoic acids with diphenyl sulfoxide/oxalyl chloride. Flavour Fragrance J. 2018, 33 (6), 397-404.
Synthesis of butenolides by reactions of 3‐alkenoic acids with diphenyl sulfoxide/oxalyl chloride
Ding, R.; Li, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Synthesis of butenolides by reactions of 3-alkenoic acids with diphenyl sulfoxide/oxalyl chloride. Flavour Fragrance J. 2018, 33 (6), 397-404.
Synthesis of butenolides by reactions of 3‐alkenoic acids with diphenyl sulfoxide/oxalyl chloride
Ding, R.; Li, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Synthesis of butenolides by reactions of 3-alkenoic acids with diphenyl sulfoxide/oxalyl chloride. Flavour Fragrance J. 2018, 33 (6), 397-404.
Synthesis of butenolides by reactions of 3‐alkenoic acids with diphenyl sulfoxide/oxalyl chloride
González, C. G.; Mustafa, N. R.; Wilson, E. G.; Verpoorte, R.; Choi, Y. H., Application of natural deep eutectic solvents for the “green”extraction of vanillin from vanilla pods. FlavourFragrance J. 2018, 33 (1), 91-96.
Application of natural deep eutectic solvents for the “green” extraction of vanillin from vanilla pods
• 2000 to 3000 tons vanilla produced every year
• <1% of vanillin in the flavor market is from vanilla
• Most extracted with aqueous ethanol (50% v/v)• Leaves potentially undesirable ethanol (up to 35% v/v)• Only non-toxic option
• Natural deep eutectic solvents (NADES) might be an option
• Ionic liquids could be useful, but they are highly toxic
• Some natural liquid mixtures have been shown to be ionic• Organic acids/bases• Could explain biological phenomena
• Unlike lipids or water, can dissolve taxol, rutin, etc.
González, C. G.; Mustafa, N. R.; Wilson, E. G.; Verpoorte, R.; Choi, Y. H., Application of natural deep eutectic solvents for the “green”extraction of vanillin from vanilla pods. FlavourFragrance J. 2018, 33 (1), 91-96.
Application of natural deep eutectic solvents for the “green” extraction of vanillin from vanilla pods
González, C. G.; Mustafa, N. R.; Wilson, E. G.; Verpoorte, R.; Choi, Y. H., Application of natural deep eutectic solvents for the “green”extraction of vanillin from vanilla pods. FlavourFragrance J. 2018, 33 (1), 91-96.
Application of natural deep eutectic solvents for the “green” extraction of vanillin from vanilla pods
Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J. 2018, 33 (4), 285-293.
Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin
• Flavoring agent
• BP: 265 °C
• Fragrance agent• Antifungal activity• BP: 248 °C
Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J. 2018, 33 (4), 285-293.
Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin
• Guest-Host technique for separation
• β-cyclodextrin (CD) showed good affinity for CAc in past reports
Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J. 2018, 33 (4), 285-293.
Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation
with β‐cyclodextrinUsing ROESY (Rotating frame Overhause Effect Spectroscopy) to probe
1H-1H coupling through space
Aromatic CAcProtons
Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J. 2018, 33 (4), 285-293.
Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation
with β‐cyclodextrinUsing ROESY (Rotating frame Overhause Effect Spectroscopy) to probe
1H-1H coupling through space
Aromatic CAProtons
Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J. 2018, 33 (4), 285-293.
Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation
with β‐cyclodextrinUsing ROESY (Rotating frame Overhause Effect Spectroscopy) to probe
1H-1H coupling through space
Aromatic CAProtons
Both show Ph-ringdeep in β-CD
Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J. 2018, 33 (4), 285-293.
Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin
Similar new peaks suggest complexes are isostructural
Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J. 2018, 33 (4), 285-293.
Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin
Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J. 2018, 33 (4), 285-293.
Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin
Chiang, N.; Ho, C. T.; Munafo Jr, J. P., Identification of key aroma compounds in raw and roasted lily bulbs (Bai He). Flavour Fragrance J. 2018, 33 (4), 294-302.http://www.ingenieria-analitica.com/downloads/dl/file/id/1226/product/95/presentacion_sniffers.pdf
Identification of key aroma compounds in raw and roasted lily bulbs (Bai He)
• Lily bulbs (‘Bai He’) are a popular ingredient in Chinese cooking
• Little is known about the odorants responsible for their distinct aroma
• Solvation followed by gas chromatography-olfactometry (GC/O) were used to identify new aroma-active compounds
Chiang, N.; Ho, C. T.; Munafo Jr, J. P., Identification of key aroma compounds in raw and roasted lily bulbs (Bai He). Flavour Fragrance J. 2018, 33 (4), 294-302.http://www.ingenieria-analitica.com/downloads/dl/file/id/1226/product/95/presentacion_sniffers.pdf
Identification of key aroma compounds in raw and roasted lily bulbs (Bai He)
Chiang, N.; Ho, C. T.; Munafo Jr, J. P., Identification of key aroma compounds in raw and roasted lily bulbs (Bai He). Flavour Fragrance J. 2018, 33 (4), 294-302.http://www.ingenieria-analitica.com/downloads/dl/file/id/1226/product/95/presentacion_sniffers.pdf
Identification of key aroma compounds in raw and roasted lily bulbs (Bai He)
• They dilute each identified compound and rate how dilute they can still smell it; this gives a flavor dilution (FD) factor• Dilute 1:1 , 1:2, …, 1:1024
• Raw: 25 odorants detected in the FD range from 1 to 1024• Roasted: 42 odorants detected in the FD range from 1 to 1024
Odorants with FD > 63 in Raw Lily Bulbs
Chiang, N.; Ho, C. T.; Munafo Jr, J. P., Identification of key aroma compounds in raw and roasted lily bulbs (Bai He). Flavour Fragrance J. 2018, 33 (4), 294-302.http://www.ingenieria-analitica.com/downloads/dl/file/id/1226/product/95/presentacion_sniffers.pdf
Identification of key aroma compounds in raw and roasted lily bulbs (Bai He)
Odorants with FD > 63 in Roasted Lily Bulbs
Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis. Flavour Fragrance J. 2018, 33 (3), 263-271.
Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by
aroma extract dilution analysis and chemical analysis
• “Pure” microorganism fermentation changes aroma profile
• Huang Jiu is a good study• 60% is from traditional techniques
• Open pottery jars• 30 to 90 days• 3 years of aging
• 40% is from modern techniques • Fermentation tanks• 20 to 30 days• 1 year of aging
• Tested with GC-O and GC-MS
Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis. Flavour Fragrance J. 2018, 33 (3), 263-271.
Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis. Flavour Fragrance J. 2018, 33 (3), 263-271.
Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis. Flavour Fragrance J. 2018, 33 (3), 263-271.
Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by
aroma extract dilution analysis and chemical analysis
Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
Synthesis of thiophene derivatives with long-lasting citrusy type odour
Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
Synthesis of thiophene derivatives with long-lasting citrusy type odour
Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
Synthesis of thiophene derivatives with long-lasting citrusy type odour
Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
Synthesis of thiophene derivatives with long-lasting citrusy type odour
Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
Synthesis of thiophene derivatives with long-lasting citrusy type odour
Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
Synthesis of thiophene derivatives with long-lasting citrusy type odour
Determined by a 6-person panel
Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis. Flavour Fragrance J. 2018, 33 (3), 263-271.
Chemistry Careers in Fragrance
Firmenich(Geneva)
IFF(Mid-Atlantic)
Givaudan(Vernier)
Symrise(Holzminden)
Takasago(Tokyo)
Frutarom(Haifa)
Sensient(Milwaukee)
Robertet(Nice)
T Hasegawa(Tokyo)
Huabao(Hong Kong)