lipidomic standards and research tools - vinci · pdf file · 2017-07-03lipidomic...
TRANSCRIPT
CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897 WWW.CAYMANCHEM.COM2018
· Ready-to-use, quantitative MaxSpec™ standards· High-purity, qualitative research standards· Stable isotope-labeled standards· Custom lipid synthesis, including stable isotope labeling· Contract lipid analysis services are available
EICOSANOIDS& FATTY ACIDS
· ESSENTIAL FATTY ACIDS· LEUKOTRIENES· LIPOXINS· MARESINS· OXYLIPINS· PROSTAGLANDINS· RESOLVINS· THROMBOXANES
· MONOACYLGLYCEROLS· DIACYLGLYCEROLS· TRIACYLGLYCEROLS
· BILE ACIDS· OXYSTEROLS· STEROIDS
· CERAMIDES· GANGLIOSIDES· SPHINGOMYELINS· SPHINGOSINES
· PHOSPHATIDIC ACIDS· PHOSPHATIDYLCHOLINES· PHOSPHATIDYLETHANOLAMINES· PHOSPHATIDYLINOSITOLS
GLYCEROLIPIDSSTEROL LIPIDS
SPHINGOLIPIDS PHOSPHOLIPIDS
LOOK INSIDE TO LEARN MORE
Eicosanoids & Fatty Acids
Mass Spec Mixtures
Glycerolipids
Phospholipids
Sphingolipids
Sterol Lipids
Pages 1-2
Pages 3-4
Page 5
Page 5 Page 5 Page 6
Lipidomic Standards and Research ToolsWith more than 35 years of experience in producing high quality research tools, Cayman Chemical is your partner in lipid research. Our scientists are experts in the synthesis, purification, and characterization of complex biolipids, fatty acids, and endogenous metabolites. We are renowned for our vast expertise in biochemistry involving the arachidonic acid cascade, resolvins, cannabinoids, and many other biochemicals, which has led to the production of a growing library of qualitative research chemicals and quantitative MaxSpec™ standards for lipidomic andmetabolomic studies. We also offer custom organic synthesis services for unique compounds and a wide range of analytical services using LC-MS/MS, HPLC, GC, and many other techniques.
CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897 WWW.CAYMANCHEM.COMPAGE 1
PGFS
8-LO
COX-2
FAAHLTC4S
LTA4H
MAGL
COX-2
COX-1COX-2
COX-1COX-2
PGISTXS
12-LO
15-LO
5-LO
15-LO
5-LO
P450
H-PGDSL-PGDS
mPGES-1mPGES-2
cPGES
COX-2+
Aspirin
5-LO
5-LO
12-LO
12-LO15-LO
5-LO
12(R)-LO
COOH
Arachidonic Acid (90010)
Prostaglandin H2 (17020)
12(S)-HpETE (44570)
Prostaglandin I2 (18220)Prostacyclin, Epoprostenol
O
HOOH
COOH
OH
HO
COOH
OH
O
6-keto Prostaglandin F1α (15210)
6-keto Prostaglandin E1 (13260)
O
OH
COOH
HO
O
6,15-diketo-13,14-dihydroProstaglandin F1α (15270)
OH
HO
COOH
O
O
2,3-dinor-6-ketoProstaglandin F1α (15120)
OH
HOOH
O
COOH
12(S)-HHTrE (34590)12(S)-HHT
COOH
OH
12-OxoHTrE12-keto HT
COOH
O
(±)5,6-EET (50211)(±)5(6)-EpETrE
COOHO
(±)11,12-EET (50511)(±)11(12)-EpETrE
COOH
O
(±)5,6-DiHET (51211)(±)5(6)-DiHETrE
OH
COOH
HO
(±)11,12-DiHET (51511)(±)11(12)-DiHETrE
OH
COOH
HO
(±)8,9-EET (50351)(±)8(9)-EpETrE
COOHO
(±)14,15-EET (50651)(±)14(15)-EpETrE
COOH
O
(±)8,9-DiHET (51351)(±)8(9)-DiHETrE
OH
COOH
HO
(±)14,15-DiHET (51651)(±)14(15)-DiHETrE
OH
COOH
HO
3(R)-HETE
OH
COOH
12(R)-HETE (34560)OH
COOH
12(R)-HETE (34560)OH
COOH
HO
COOH
11(R)-HETE (34505)
12(R)-HpETEOOH
COOH
tetranor-12(R)-HETE (34565)8(R)-HHxTrE
COOH
HO
12-OxoETE (34580)12-KETE
COOH
O
19(R)-HETE (10007767)
COOH
OH
5(S)-HpETE (44230)
Thromboxane B2 (19030)
O
OH
COOH
OH
HO
11-dehydro Thromboxane B2 (19500)11-keto TXB2
OO
OH
OH
COOH
2,3-dinor Thromboxane B2 (19050)
O
OH
OH
HO
COOH
11-dehydro-2,3-dinorThromboxane B2 (19510)
OO
OH
COOH
OH
Thromboxane A2
O
OCOOH
OH
2,3,4,5-tetranor Thromboxane B2
O
OH
OH
HO
COOH
Prostaglandin G2 (17010)
O
O
COOH
OOH
Prostaglandin D2 (12010)
OH
COOH
OH
O
11β-Prostaglandin F2α (16520)OH
OH
HO
COOH
Prostaglandin J2 (18500)
COOH
OH
O
Δ12-Prostaglandin J2 (18550)
COOH
OH
O
15-deoxy-Δ12,14-Prostaglandin J2 (18570)
COOH
O
13,14-dihydro-15-keto Prostaglandin D2 (12610)
OH
COOH
OO
19(R)-hydroxy Prostaglandin F2α (16910)
OH
OH
HO
COOH
OH
Prostaglandin F2α (16010)Dinoprost
OH
OH
HO
COOH
15-keto Prostaglandin F2α (16720)
OH
HO
COOH
O
13,14-dihydro-15-keto Prostaglandin F2α (16670)
OH
HO
COOH
O
tetranor-PGFM (16840)
OH
HO
COOH
O
COOH
COOH
Prostaglandin K2 (18900)
COOH
OH
O
O
Prostaglandin E2 (14010)Dinoprostone
O
OHHO
COOH
15-keto Prostaglandin E2 (14720)
O
COOH
HOO
13,14-dihydro-15-ketoProstaglandin E2 (14650)
O
COOH
HOO
Prostaglandin A2 (10210)Medullin
COOH
OH
O
19(R)-hydroxy Prostaglandin E2 (14910)
O
OHHO
COOH
OH
Prostaglandin B2 (11210)
COOH
OH
O
13,14-dihydro-15-keto Prostaglandin A2 (10260)
COOH
O
O
tetranor-PGEM (14840)
O
COOH
HOO
COOH
tetranor-PGDM (12850)
OH
O
O
COOH
COOH
Prostaglandin C2
COOH
OH
O
Arachidonoyl Ethanolamide (90050)AEA, Anandamide
NHHO
O
Prostaglandin F2α Ethanolamide (16013)Dinoprost Ethanolamide
OH
OH
HO
O
H
NOH
Prostaglandin E2 Ethanolamide (14012)Dinoprostone Ethanolamide
OO
OH
HO
N
H
HO
Prostaglandin D2 Ethanolamide (12012)OH
OH
O
O
H
NOH
20-hydroxy Prostaglandin F2α (16950)
OH
OH
HO
COOH
OH
Prostaglandin H2 Ethanolamide
O
O
OH
OH
O
H
N
5(S)-HETE (34230)
OH
COOH
5-OxoETE (34250)
COOHO
6-trans Leukotriene B4 (35250)5(S),12(R)-DiHETE, all trans LTB4
OH
OH
COOH
5(S),6(R)-DiHETE (35200)(+ 5(R),6(R)-DiHETE)
OH
OH
COOH
5(S),6(S)-DiHETE (35210)(+ 5(R),6(S)-DiHETE)
OH
OH
COOH
6-trans-12-epi Leukotriene B4 (35265)5(S),12(S)-DiHETE
OH
OH
COOH
Leukotriene B4 (20110)
COOH
OHOH
12-oxo Leukotriene B4 (20140)12-keto LTB4
OCOOH
OH
20-hydroxy Leukotriene B4 (20190)
COOH
OHOH
OH
10,11-dihydro Leukotriene B4
COOH
OHOH
12-keto-10,11-dihydro Leukotriene B4
OCOOH
OH
20-carboxy Leukotriene B4 (20180)
COOH
OHOH
COOH
18-carboxy dinor Leukotriene B4 (20170)
COOH
OHOH
COOH
Leukotriene D4 (20310)
OH
SCONHCH2COOH
NH2
COOH
N-acetyl-14-carboxy hexanor Leukotriene E3
OH
SCOOH
NHCOCH3
COOH
COOH
OH
COOH
OH
5(S),12(S)-DiHETE
15(R)-HETE (34710)
COOH
OH
15(S)-HETE (34720)
COOH
OH
5(S),15(S)-DiHETE (35280)
OH
COOH
OH
12-OxoETE (34580)12-KETE
COOH
O
12(S)-HETE (34570)
OH
COOH
14,15-Leukotriene E4 (10011362)Eoxin E4
COOHOH
SCOOH
NH2
5(S)-Hp-15(S)-HETE
COOH
OOH
OH
12-OxoETE-GSH
COOH
O
SO
HNH
NHOOC
O
COOH
NH2
12-OxoDTrE
COOH
CHO
COOH
OHO
Hepoxilin A38-hydroxy-11(S),12(S)-EET
8,11,12-TriHETrE
OH
COOH
HO
HO
OHO
COOH
Hepoxilin B310-hydroxy-11(S),12(S)-EET
10,11,12-TriHETrEOHHO
HO
COOH
2-Arachidonoyl Glycerol (62160)2-AG
O OH
OH
O
8(S),15(S)-DiHETE (35370)
OH
OH
COOH
Leukotriene A4 (20010; methyl ester)
15(S)-HpETE (44720)
20-hydroxy Prostaglandin D2
O
COOH
OH
OH
OH
Prostaglandin I2 Ethanolamide
O
HOOH
NH
OOH
15(R)-Lipoxin B4
OH
OH
OH
COOH
12(S)-HETE (34570)
OH
COOH
Prostaglandin I2 Glycerol
O
HO
OH
OO
OH
OH
Prostaglandin E2 GlycerolOH
HO
OO
O
OH
OH
Prostaglandin D2 GlycerolOH
O
OH
O
O
OH
OH
Prostaglandin F2α Glycerol
OHHO
OH
O
O
OH
OH
Prostaglandin H2 Glycerol
O
O
OH
O
O
OH
OH
Lipoxin A4 (90410)OH
COOH
OHHO
Lipoxin B4 (90420)
COOH
OH
OHHO
Lipoxin A4 (90410)OH
COOH
OHHO
Lipoxin B4 (90420)
COOH
OH
OHHO
2,3-dinor-6,15-diketo-13,14-dihydro Prostaglandin F1a
OH
HO
COOH
O
O
5(S),6(S)-epoxy-15(S)-HETE
COOHO
HO
5(S),6(S)-epoxy-15(S)-HETE
COOHO
HO
5(S),6(S)-epoxy-15(R)-HETE
COOHO
HO
2,3-dinor-11β-Prostaglandin F2α (16530)OH
OH
HO
COOH
PGDM (13454)Prostaglandin D Metabolite
HO
HO
COOH
COOH
O
20-hydroxy Prostaglandin E2 (14950)
O
OHHO
COOH
OH
Prostaglandin F2β (16410)9β-PGF2α
COOH
OH
OH
HO
N-acetyl Leukotriene E4 (20420)
OH
SCOOH
NHCOCH3
COOH
19(S)-HETE (10007766) OH
COOH
20-HETE (90030)
COOH
OH
14,15-Leukotriene D4Eoxin D4
COOHOH
NH2
S NCH2COOH
O
H
14,15-Leukotriene C4 (10011360)Eoxin C4
COOHOH
S
NH
NCH2COOH
COOH
O
O
NH2
H
8(S)-HETE (34360)
COOH
OH
8(S)-HpETE
COOH
OOH
Leukotriene C4 (20210)
OH
COOH
S
NH
O
N
H
O
CH2COOH
COOH
NH2
Leukotriene E4 (20410)
OH
SCOOH
COOH
NH2
20-hydroxy Leukotriene E4
OH
SCOOH
COOH
OH
NH2
N-acetyl-20-carboxy Leukotriene E4
OH
SCOOH
NHCOCH3
COOH
COOH
20-carboxy Leukotriene E4
OH
SCOOH
NH2
COOH
COOH
18-carboxy dinor Leukotriene E4
OH
SCOOH
NH2
COOH
COOHN-acetyl-18-carboxy dinor Leukotriene E4
OH
SCOOH
NHCOCH3
COOH
COOH
N-acetyl-16-carboxy tetranor Leukotriene E3
OH
SCOOH
NHCOCH3
COOH
COOH
16-carboxy tetranor Leukotriene E3
OH
SCOOH
NH2
COOH
COOH
16-carboxy-Δ13-tetranor Leukotriene E4
OH
SCOOH
NH2
COOH
COOH
14-carboxy hexanor Leukotriene E3
OH
SCOOH
NH2
COOH
COOH
N-acetyl-16-carboxy-Δ13-tetranor Leukotriene E4
COOH
COOHS
NHCOCH3
OH
COOH
5-OxoETE-GSHFOG7
HOOCS
O O
H
NCH
2COOH
HN
O
COOH
NH2
15(R)-Lipoxin A4 (90415)
OH
HO OH
COOH
11(R)-HpETE(Minor COX reaction product)
COOH
HOO
11β-15-keto Prostaglandin F2α
OH
COOH
OHO
OH
COOH
OO
15-keto Prostaglandin D2
11β-13,14-dihydro-15-ketoProstaglandin F2α (16540)
OH
HO
COOH
O
15-deoxy-Δ12,14-Prostaglandin D2 (12700)
OH
COOH
O
PLA2
14,15-Leukotriene A4Eoxin A4
COOHO
This illustration presents, in detail, the cyclooxygenase, lipoxygenase, and CYP450 pathways, which are the three main branches of the arachidonic acid cascade. Metabolism of polyunsaturated fatty acids results in the biosynthesis of potent mediators with far-ranging physiological effects. These metabolites include prostaglandins, prostacyclins, thromboxanes, leukotrienes, lipoxins, and hydroperoxy, hydroxy, and epoxy fatty acids. Virtually any unsaturated fatty acid with a 1,4-pentadienyl structural element is apossible substrate for one or more of the aforementioned pathways. Linoleic, linolenic, dihomo-γ-linolenic, eicosatetraenoic(arachidonic), eicospentaenoic, and docosoahexaenoic acids are examples of such substrates. Arachidonic acid is the only substrate illustrated here, since it is the major in vivo substrate in many species, including humans. Most of the compounds shown in this chart, as well as those derived from other polyunsaturated fatty acids, are available from Cayman Chemical.
ARACHIDONIC ACID CASCADE
HETEsLeukotrienesProstaglandins
ThromboxanesEndocannabinoids
EnzymaticNon-enzymaticMultiple Steps
HETEs
Leukotrienes Endocannabinoids
Thromboxanes Prostaglandins
Request the full Arachidonic Acid Cascade wall poster at www.caymanchem.com/Literature
Eicosanoids and Fatty AcidsEicosanoids: The major branches of the arachidonic acid cascade represent the metabolism of polyunsaturated fatty acids into potent mediators with far-ranging physiological effects. These metabolites include prostaglandins, prostacyclins, thromboxanes, leukotrienes, lipoxins, and hydroperoxy, hydroxy, and epoxy fatty acids. Cayman Chemical has pioneered the production of synthetically pure versions of these lipids and developed methods for their accurate measurement. From the most well-known to the very obscure, we offer thousands of high purity standards for this area of research.
Leukotrienes
Common leukotrienes listed, over 55 leukotrienes available online
Common oxylipins listed, over 200 oxylipins available online
Common prostaglandins listed, over 400 prostaglandins available online
Common thromboxanes listed, over 20 thromboxanes available online
Oxylipins
Prostaglandins
Thromboxanes
Item No. Product Name
20110 Leukotriene B4
320110 Leukotriene B4-d4
20210 Leukotriene C4
10006198 Leukotriene C4-d5
20310 Leukotriene D4
10006199 Leukotriene D4-d5
20410 Leukotriene E4
10007858 Leukotriene E4-d5
20520 Leukotriene F4
Item No. Product Name
50651 (±)14(15)-EET
10006410 (±)14(15)-EET-d11
50861 (±)17(18)-EpETE
34720 15(S)-HETE
334720 15(S)-HETE-d8
90030 20-HETE
44570 12(S)-HpETE
44720 15(S)-HpETE
Item No. Product Name
14840 tetranor-PGEM
16840 tetranor-PGFM
14720 15-keto Prostaglandin E2
15120 2,3-dinor-6-keto Prostaglandin F1α (sodium salt)
15210 6-keto Prostaglandin F1α
16520 11β-Prostaglandin F2α
16530 2,3-dinor-11β-Prostaglandin F2α
16350 8-iso Prostaglandin F2α
18570 15-deoxy-Δ12,14-Prostaglandin J2
Item No. Product Name
19010 Carbocyclic Thromboxane A2
19030 Thromboxane B2
319030 Thromboxane B2-d4
19500 11-dehydro Thromboxane B2
319500 11-dehydro Thromboxane B2-d4
19510 11-dehydro-2,3-dinor Thromboxane B2
19050 2,3-dinor Thromboxane B2
10009584 2,3-dinor Thromboxane B2-d9
View a complete list of our eicosanoids & fatty acids Please visit us online at www.caymanchem.com
CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897WWW.CAYMANCHEM.COM PAGE 2
SPECIALIZED PRO-RESOLVING MEDIATORS The resolution of inflammation is an active process that is driven by unique signaling molecules. An important group of these specialized pro-resolving mediators (SPMs) is derived from polyunsaturated fatty acids (arachidonic acid (AA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA), and docosahexaenoic acid (DHA)) that are liberated during the inflammatory process. Studies have demonstrated that these SPMs, which include resolvins, lipoxins, maresins, and protectins, evoke cellular and tissue responses that help conclude an inflammatory episode. Moreover, the addition of nanomolarconcentrations of SPMs to an inflammatory milieu can have profound effects, such as reducing leukocyte infiltration, enhancing phagocytosis, and reducing pain. Cayman Chemical, a leader in the synthesis of lipid mediators, offers an array of SPMs to help make your research possible.
www.caymanchem.com
COOH
DHA (90310)
13(S),14(S)-epoxy-MaresinCOOH
O
Maresin 2 (16369)
COOH
OH
HO
14(S)-HpDHACOOH
OOH
15-LO
15-LO12-LO
SolubleEpoxide
Hydrolase
Maresin 1 (10878)
COOH
OH
OH
Hydrolase 14(S)-HDHA (15253)
COOH
OH
14(S),21(R)-HDHA
COOH
OHOH
17(S)-HpDHA (13185)
COOH
HOO
Protectin D1/Neuroprotectin D1 (10010390)
OH
OH
COOH
10(S),17(S)-DiHDHA (PDX) (10008128)
OH
COOH
OH
16(S),17(S)-epoxy Protectin
COOHO
15-LO
5-LO
17(S)-HpDHA (13185)
COOH
HOO
Resolvin D1 (10012554)(17(R)-Resolvin D1, 13060)
HO
COOH
HO
OH
Resolvin D2 (10007279)
COOH
HO
HO
OH
Resolvin D5 (10007280)
COOH
HO
HO
7(S)-hydroperoxy-17(S)-HDHAHO
COOH
HOO
Resolvin D3 (13834)
COOH
OH
OH
HO
Resolvin D6 (10484)
HOOC
OH
OH
4(S)-hydroperoxy-17(S)-HDHA
HO
COOHHOO
7(S),8(S)-epoxy-17(S)-HDHAHO
COOH
O
4(S),5(S)-epoxy- 17(S)-HDHA
HO
COOH
O
5-LO
5-LO
Resolvin D4 (13835)
COOH
HO
HO
OH
14(S),20(R)-DiHDHA (19139)
COOH
OH
HO
D-Resolvin Family
Protectin Family
Maresin Family
PCTR2 (19065)
COOH
S
OH
H2N
NH
O
COOH
PCTR3 (19066)
COOH
S
OH
H2N
HOOC
MCTR1 (17007)
COOH
OH
S
NH
O
HOOC
NH2HN
O
HOOC
MCTR2 (17008)COOH
OH
S
NH2HN
O
HOOC
MCTR3 (19067)COOH
OH
SHOOC
NH2
COOHS
OH
NH
O
H2N
COOH NH
O
COOH
PCTR1 (19064)
COOH
OH
OH
OH
COOH
Resolvin T1 (18437)
OH
OH
OH
COOH
Resolvin T2 (18438)
OH
OH
OH
COOH
Resolvin T3 (18439)
OH OH
COOH
Resolvin T4 (18440)
DPA (90165)
T-Resolvin Family
COX-2
COOH
HOO 13(R)-HpDPA
COOH
HO 13(R)-HDPA
E-Resolvin Family
COOH
EPA (90110)P450 Aspirin & COX-2
HOCOOHOH
OH
Resolvin E1 (10007848)
OH
COOH
OH
Resolvin E2 (13827)
COOH
OHHO Resolvin E3
COOH
OOH18(R)-HpEPE
COOH
OH18(R)-HEPE
OH
COOH
OOH
5(S)-hydroperoxy-18(R)-HEPE
OH
COOHO
5(S),6(S)-epoxy-18(R)-HEPE
5-LO
Lipoxin Family
COOH
AA (90010)
15-LO 5-LO
5-LO
Lipoxin A4 (90410)(15(R)-Lipoxin A4, 90415)
OH
COOH
OHHO
*5(S)-HpETE (44230)
COOH
OOH
*15(S)-HpETE (44720)
COOH
OOH
*5(S),15(S)-DiHpETE
COOH
OOH
OOH
COOHO
HO
*5(S),6(S)-epoxy-15(S)-DiHETE
Lipoxin B4 (90420)
COOH
OH
OHHO
*Have not been shown to have pro-resolving properties in published literature
Request the full Specialized Pro-Resolving Mediators wall poster at www.caymanchem.com/Literature
Eicosanoids and Fatty AcidsSpecialized Pro-Resolving Mediators: An important group of signaling molecules derived from arachidonic acid, eicosapentaenoic acid, docosapentaenoic acid, and docosahexaenoic acid are liberated during the inflammatory process and perform key immunoregulatory actions. Studies have shown that resolvins, lipoxins, maresins, and protectins evoke responses that help to resolve an inflammatory episode back to a non-inflamed state. Cayman has synthesized an array of these key lipid mediators to aid in a better understanding of this process.
Fatty Acids: Fatty acids are categorized into several groups based on the length of their aliphatic chain. Among their important biological functions, they serve as building blocks of amphipathic molecules. Cayman offers various important essential fatty acids as well as endogenous fatty acids, including those that serve as precursors in the production of many other lipids. This includes a newly discovered class of branched fatty acid esters of hydroxy fatty acids (FAHFAs) that are produced naturally in adipose tissue and are associated with insulin sensitivity.
Common resolvins listed, more resovlins available online Common maresins listed, more maresins available online
Common essential fatty acids listed, over 50 essential fatty acids available online
Common lipoxins listed, more lipoxins available online
Resolvins Lipoxins
Essential Fatty Acids
Maresins
Item No. Product Name
15253 14(S)-HDHA
10012554 Resolvin D1
13060 17(R)-Resolvin D1
10007279 Resolvin D2
11184 Resolvin D2-d5
13834 Resolvin D3
10007848 Resolvin E1
Item No. Product Name
90410 Lipoxin A4
90420 Lipoxin B4
Item No. Product Name
90010 Arachidonic Acid
390010 Arachidonic Acid-d8
90310 Docosahexaenoic Acid
10005057 Docosahexaenoic Acid-d5
90110 Eicosapentaenoic Acid
10005056 Eicosapentaenoic Acid-d5
Item No. Product Name
10878 Maresin 1
16369 Maresin 2
Maximize time. Maximize results.A new line of ready-to-use, quantitative standards prepared specifically for mass spectrometry applications.
Verified concentration LC-MS identity test HPLC purity test Ongoing stability testing
MaxSpecTM Quality GuaranteeMaxSpec™ Standards
CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897 WWW.CAYMANCHEM.COMPAGE 3
Fatty Acid and Eicosanoid Mass Spec Mixtures
Bioactive Eicosanoids, Precursors, & Metabolites
Commonly analyzed lipids can also be purchased in:Quant-PAKs
· Includes a 50 µg vial of a deuterium-labeled lipid and a precisely weighed vial of unlabeled lipid · Designed for the convenient analysis of lipids by GC- or LC-MS
HPLC Mixtures · Contains a mixture of lipid standards packaged for HPLC use · Each compound supplied either in ethanol or methyl acetate
Oxylipins
Specialized Pro-Resolving Mediators
*Stable isotope-labeled mixtures are also available
*Stable isotope-labeled mixtures are also available
Item No. Product Name Supplied As Contains (1 μg/ml of each compound)
19101 Primary COX and LOX LC-MS Mixture* 1 or 5 ampules/pack 6-keto Prostaglandin F1α, Thromboxane B2, Prostaglandin F2α, Prostaglandin E2,
Prostaglandin D2, 12(S)-HHTrE, 15(S)-HETE, 12(S)-HETE, 5(S)-HETE
19300 Primary Prostaglandin Metabolite LC-MS Mixture* 1 or 5 ampules/pack
11β-Prostaglandin F2α, 15-keto Prostaglandin F2α, 15-keto Prostaglandin E2, 13,14-dihydro-15-keto Prostaglandin F2α, 13,14-dihydro-15-keto Prostaglandin E2, 13,14-dihydro-15-keto Prostaglandin D2, Prostaglandin J2,15-deoxy-Δ12,14-Prostaglandin J2
19422 Secondary Prostaglandin Metabolite LC-MS Mixture 1 ampule
tetranor-PGFM, tetranor-PGEM, tetranor-PGDM, 13,14-dihydro-15-ketoProstaglandin F2α, 13,14-dihydro-15-keto Prostaglandin E2, 13,14-dihydro-15-keto Prostaglandin D2
Item No. Product Name Supplied As Contains (1-10 μg/ml of each compound)
20665 Arachidonic Acid CYP450 Metabolite LC-MS Mixture* 1 ampule (±)14(15)-DiHETE, (±)5(6)-DiHETE, 20-HETE, 19(R)-HETE, (±)14(15)-EET,
(±)11(12)-EET, (±)8(9)-EET
20666 Arachidonic Acid OxylipinLC-MS Mixture* 1 ampule 15(S)-HETE, 11(S)-HETE, 15-OxoETE, 8(S)-HETE, 12(S)-HETE, 9(R)-HETE,
5(S)-HETE, 12-OxoETE, 5-OxoETE
21393 EPA Oxylipin LC-MS Mixture 1 ampule Prostaglandin E3, Prostaglandin F3α, 5(S)-HEPE, (±)8-HEPE, (±)9-HEPE, (±)11-HEPE, 12(S)-HEPE, 15(S)-HEPE, (±)18-HEPE
Item No. Product Name Supplied As Contains (100 ng/ml of each compound)
19412 Lipoxin LC-MS Mixture 1 ampule Lipoxin B4, Lipoxin A4, 15(R)-Lipoxin A4, Arachidonic Acid
18702 SPM D-series LC-MS Mixture 1 ampule Resolvin D3, Resolvin D2, 17(R)-Resolvin D1, Resolvin D1, Resolvin D5, Docosahexaenoic Acid
19417 SPM E-series LC-MS Mixture 1 ampule Resolvin E1, (±)18-HEPE, Eicosapentaenoic Acid
· Contains a mixture of lipid standards packaged in amber ampules purged with argon
· Each compound provided in ethanol (1 ml/ampule, nominal) · Designed for direct snap and inject use in GC- or LC-MS applications
CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897WWW.CAYMANCHEM.COM PAGE 4
Dietary & Microbiome-Related Fatty Acids
Vasoactive Eicosanoids
Oxidative Stress
Item No. Product Name Supplied As Contains (10 μg/ml of each compound)
18824 Short-Chain Fatty Acid LC-MS Mixture 1 ampule
Propionic Acid (C3:0), Butyric Acid (C4:0), Hexanoic Acid (C6:0), Heptanoic Acid (C7:0), Octanoic Acid (C8:0), Nonanoic Acid (C9:0), Decanoic Acid (C10:0), Dodecanoic Acid (C12:0)
19227 Odd-Chain Fatty Acid LC-MS Mixture 1 ampule
Undecanoic Acid (C11:0), Tridecanoic Acid (C13:0), 14-Pentadecenoic Acid (C15:1), Pentadecanoic Acid (C15:0), cis-10-Heptadecenoic Acid (C17:1), Heptadecanoic Acid (C17:0), cis-10-Nonadecenoic Acid (C19:1), Nonadecanoic Acid (C19:0)
17941 Polyunsaturated Fatty AcidLC-MS Mixture 1 ampule
Adrenic Acid (C22:4), Arachidonic Acid (C20:4), Dihomo-γ-Linolenic Acid (C20:3), Docosahexaenoic Acid (C22:6), Docosapentaenoic Acid (C22:5), Eicosapentaenoic Acid (C20:5), Linoleic Acid (C18:2), α-Linolenic Acid (C18:3 n-3), γ-Linolenic Acid (C18:3 n-6), Stearidonic Acid (C18:4)
17942 Saturated/Monounsaturated Fatty Acid LC-MS Mixture 1 ampule
Arachidic Acid (C20:0), Lauric Acid (C12:0), Lignoceric Acid (C24:0), Myristic Acid (C14:0), Nervonic Acid (C24:1), Oleic Acid (C18:1), Palmitic Acid (C16:0), Palmitoleic Acid (C16:1), Stearic Acid (C18:0)
Item No. Product Name Supplied As Contains (1 mg/ml of each compound)
20503 Fatty Acid methyl ester GC-MS Mixture 1 ampule
Methyl ester forms of: Lauric Acid, Myristic Acid, Palmitoleic Acid, Palmitic Acid, γ-Linolenic Acid, Stearidonic Acid, Linoleic Acid, Oleic Acid, Linolenic Acid, Stearic Acid, Arachidonic Acid, Eicosapentaenoic Acid, Dihomo-γ-Linolenic Acid, ω-3 Arachidonic Acid, Eicosadienoic Acid, 11(Z),14(Z),17(Z)-Eicosatrienoic Acid, Heneicosapentaenoic Acid, Docosahexaenoic Acid, cis-4,10,13,16-Docosatetraenoic Acid, Docosapentaenoic Acid
Item No. Product Name Supplied As Contains (1 μg/ml of each compound)
19667 Primary Vascular EicosanoidLC-MS Mixture 1 ampule 6-keto Prostaglandin F1α, Thromboxane B2, 11-dehydro Thromboxane B2, 12(S)-HHTrE, 20-HETE,
12(S)-HETE, 12(S)-HETrE, (±)14(15)-EET, (±)11(12)-EET, (±)8(9)-EET
19668 Vascular Eicosanoid Urinary Metabolite LC-MS Mixture 1 ampule 2,3-dinor-6-keto Prostaglandin F1α, 2,3-dinor Thromboxane B2, 11-dehydro-2,3-dinor Thromboxane B2,
11-dehydro Thromboxane B2, (±)14(15)-DiHET, (±)11(12)-DiHET, (±)8(9)-DiHET, 20-HETE
Item No. Product Name Supplied As Contains (1 μg/ml of each compound)
18701 Oxidative Stress LC-MS Mixture 1 ampule
8-Hydroxyguanosine, 8-Hydroxy-2’-deoxyguanosine, 2,3-dinor-8-iso Prostaglandin F2α, 8-iso Prostaglandin F1α, 8-iso Prostaglandin F2α, 5-iPF2α-VI, 8-iso-15-keto Prostaglandin F2α, 8-iso Prostaglandin E2, 8,12-iso-iPF2α-VI
Fatty Acid and Eicosanoid Mass Spec Mixtures
Looking to create your own customized MS mixture? Email us at [email protected]
CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897 WWW.CAYMANCHEM.COMPAGE 5
Sialidase-1
β-Galactosylceramidase
Sphingosine β-Galactosyltransferase
S1P Phosphatase
Sphingosine Kinase
β-1,4-Galactosidase
β-1,4-Galactosyltransferase 6
Ceramide Galactosyltransferase
β-Galactosylceramidase
Sphingomyelinase
Sphingomyelin Synthase
Phosphatidate Phosphatase
Ceramide Kinase
Ceramide Synthase
Ceramidase
L-Serine + Palmitoyl-CoA
3-Ketosphinganine
Sphinganine
Dihydroceramide
Galactosylceramide
Sphingomyelin
Sulphatide
Psychosine
Psychosine
GM4
GlucosylceramideLactosylceramide
Glycosphingolipids(lacto-, neolacto-, globo-, ganglio-series)
Ceramide
Long-chain Acyl-CoA Synthetase
Glucosylceramidase
Glucosylceramide Synthase
Serine Palmitoyltransferase
3-Ketosphinganine Reductase
Ceramide Synthase
Dihydroceramide Desaturase
AMP-Deoxynojirimycin (10010332)Conduritol B epoxide (15216)
2-fluoro Palmitic Acid (90380)Triacsin C (10007448)
Myriocin (63150)
L-Cycloserine (17780)
D609 (potassium salt) (13307)
NVP-231 (13858)
2-Acetyl-5-tetrahydroxybutyl Imidazole (13222)
Fumonisin B1 (62580)Fumonisin B2 (13227)Fumonisin B3 (20434)
Fumonisin B1 (62580)Fumonisin B2 (13227)Fumonisin B3 (20434)
PDMP (hydrochloride) (62595)DL-threo-PDMP (hydrochloride) (10005276)
N-(n-Butyl)deoxygalactonojirimycin (19520)N-Butyldeoxynojirimycin (hydrochloride) (21065)Eliglustat (hemitartrate) (21487)PDMP (hydrochloride) (62595)DL-threo-PDMP (hydrochloride) (10005276)DL-threo-PPMP (hydrochloride) (17236)
CAY10621 (13371)N,N-Dimethylsphingosine (62575)K145 (hydrochloride) (11691)PF-543 (17034)Safingol (18624)SLP7111228 (hydrochloride) (23290)Sphingosine Kinase Inhibitor 2 (10009222)
ARN14974 (17119)Carmofur (14243)Ceranib-2 (11092)D-erythro-MAPP (10165)D-NMAPPD (10006305)
1-Aminodecylidene bis-Phosphonic Acid (sodium salt) (13583)Benztropine (mesylate) (16214)cis-Flupenthixol (hydrochloride) (17634)GW 4869 (hydrochloride hydrate) (13127)Tomatidine (hydrochloride) (16938)
GalactosylceramideSulfotransferase
Ceramide-1-Phosphate
Sphingosine
Sphingosine-1-Phosphate (S1P)
Ethanolamine-1-Phosphate +C16-Fatty Aldehyde
S1P Lyase
Inhibitors Available
N-Deacylase Request the Specialized Primary Pathways for Sphingolipid Synthesis brochure by visiting www.caymanchem.com/Literature
· Glycerolipids · Phospholipids · SphingolipidsSphingolipids: Ceramide is the intermediate in the formation of multiple types of sphingolipids: sphingosine, sphingomyelin, ceramide-1-phosphate, glucosylceramide, and galactosylceramide. These lipids modulate cell-cell interactions and are important for various cellular functions, including differentiation, proliferation, and programmed cell death. Cayman carries many different ceramide and sphingolipid research tools to help you study distinct aspects of this important lipid signaling pathway.
Glycerolipids: Glycerolipids are composed of mono-, di-, or trisubstituted glycerols. Diacylglycerols are produced by the PLC-dependent hydrolysis of membrane phospholipids and act as lipid second messengers. Esters formed from arachidonic acid linked to glycerol are known as endocannabinoids.
Phospholipids: Phospholipids are a major component of cell membranes, forming lipid bilayers due to their amphiphilic nature. The phosphate group can be modified with simple organic molecules such as choline or ethanolamine. Phospholipids have been widely used to prepare nanoformulations for drug delivery or other types of artificial membranes.
Sphingolipids
Glycerolipids
Phosphatidylinositols
Item No. Product Name
24464 C18 Ceramide-1-Phosphate-d3 (d18:1/18:0-d3)
22789 C24 Ceramide-d7 (d18:1-d7/24:0)
22442 EOS (18:1/32:1/18:2)
24348 C17 3’-sulfo Galactosylceramide (d18:1/17:0)
23212 13C6 Glucosylsphingosine (d18:1)
62570 Sphingosine-1-phosphate (d18:1)
Item No. Product Name
62160 2-Arachidonoyl Glycerol
362162 2-Arachidonoyl Glycerol-d5
362160 2-Arachidonoyl Glycerol-d8
62225 1,2-Dioctanoyl-sn-glycerol
10008650 1-Stearoyl-2-Arachidonoyl-sn-Glycerol
10009872 1-Stearoyl-2-Arachidonoyl-sn-Glycerol-d8
Item No. Product Name
10008438 D-myo-Inositol-1,4-diphosphate (sodium salt)
10008418 D-myo-Inositol-4,5-diphosphate (sodium salt)
10008425 D-myo-Inositol-3,4,5-triphosphate (sodium salt)
9000304 PtdIns-(1-arachidonoyl-d8, 2-arachidonoyl) (sodium salt)
9000305 PtdIns-(1-arachidonoyl, 2-arachidonoyl-d8) (ammonium salt)
10008099 PtdIns-(1,2-dioctanoyl) (sodium salt)
10007710 PtdIns-(1,2-dipalmitoyl) (ammonium salt)
10007711 PtdIns-(4)-P1 (1,2-dioctanoyl) (ammonium salt)
64923 PtdIns-(4)-P1 (1,2-dipalmitoyl) (ammonium salt)
10007763 PtdIns-(3,5)-P2 (1,2-dioctanoyl) (sodium salt)
64910 PtdIns-(4,5)-P2 (1,2-dioctanoyl) (sodium salt)
10007764 PtdIns-(3,4,5)-P3 (1,2-dioctanoyl) (sodium salt)
64920 PtdIns-(3,4,5)-P3 (1,2-dipalmitoyl) (sodium salt)
9000414 PtdIns-(3,4,5)-P3 (1,2-dipalmitoyl)-d62 (sodium salt)
64930 PtdIns-(3,4,5)-P3 (1-stearoyl, 2-arachidonoyl) (sodium salt)
Common sphingolipids listed, over 100 sphingolipids available online
Common glycerolipids listed, over 50 glycerolipids available online Common phosphatidylinositols listed, over 75 phosphatidylinositols available online
CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897WWW.CAYMANCHEM.COM PAGE 6
Sterol LipidsThese naturally occurring lipids are derived from hydroxylated polycyclic isopentenoids and are known to have a wide range of biological activities and physical properties from sustaining the domain structure of cell membranes to orchestrating signaling actions throughout the body. Cayman offers a wide range of primary and secondary bile acids, SCFAs, polyamines, and additional related metabolites for this important area of research.
Oxysterols
Steroids
Bile AcidsItem No. Product Name
10007601 5α-hydroxy-6-keto Cholesterol
89355 22(R)-hydroxy Cholesterol
10009931 24(S)-hydroxy Cholesterol
14790 25(R)-27-hydroxy Cholesterol
Item No. Product Name
15728 Dehydroepiandrosterone
16146 17α,20β-Dihydroxy-4-pregnen-3-one
10006315 17β-Estradiol
16155 Estradiol 3-(β-D-Glucuronide) (sodium salt)
13019 2-Hydroxyestradiol
16145 20-hydroxy Ecdysone
18226 Hydrocortisone 21-hemisuccinate (sodium salt)
10006318 Levonorgestrel
9002042 Mebolazine
10006317 Mifepristone
Item No. Product Name
10011286 Chenodeoxycholic Acid
20250 Cholic Acid
9002532 Cholic Acid 7-sulfate
20756 Deoxycholic Acid
16942 Glycochenodeoxycholic Acid (sodium salt)
22670 Glycohyocholic Acid
22643 Glycohyodeoxycholic Acid
20273 Glycolithocholic Acid (sodium salt)
20253 Lithocholic Acid
20292 ω-Muricholic Acid
20290 Murideoxycholic Acid
16215 Taurocholic Acid (sodium salt)
9002538 Taurocholic Acid 3-sulfate
15935 Taurodeoxycholic Acid (sodium salt)
22669 Taurohyocholate
17275 Taurolithocholic Acid (sodium salt)
20277 Tauroursodeoxycholic Acid
Need Custom Synthesis of your particular lipid? Email us at [email protected]
Common oxysterols listed, over 20 oxysterols available online
Common bile acids listed, over 25 bile acids and their internal standards available online Common steroids listed, over 20 steroids available online
Custom Synthesis Spotlight: When our customer needed to optimize blood-brain barrier transport of CDDO in their experimental model, we synthesized this trifluoroethylamide derivative.
CDDO-TFEA - Item No. 90001845 A trifluoroethylamide derivative of CDDO that enhances Nrf2 expression and signaling in various models of neurodegeneration; demonstrates anticancer activity against several neuroblastoma cell lines with IC50s = 85-170 nM
H
H
O
O
NC
H H
N
O
CF3
Synthetic Triterpenoid Enhances Nrf2 Expression
CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897 WWW.CAYMANCHEM.COM2018
CONTACT US
PHONE: (800) 364-9897 (USA and Canada only) (734) 971-3335
FAX: (734) 971-3640
WEB: www.caymanchem.com
EMAIL: Sales: [email protected] Customer Service: [email protected] Technical Support: [email protected]
ADDRESS: 1180 E. Ellsworth Rd. · Ann Arbor, MI · 48108 · USA
Cayman proudly supports the LIPID MAPS® Consortium Providing lipid standards to the LIPID MAPS® Library
®
In Italy: Vinci-Biochem SrlContatto diretto: tel. 0571 568 [email protected]
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