lipidomics standards and research tools · synthesis, purification, and characterization of complex...
TRANSCRIPT
2019 WWW.CAYMANCHEM.COMCAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897
· Ready-to-use, quantitative MaxSpec® standards
· High-purity, qualitative research standards
· Stable isotope-labeled standards
· Custom lipid synthesis, including stable isotope labeling
· Lipidomic profiling services
FATTY ACYLS
� EICOSANOIDS· DOCOSANOIDS· FATTY ACIDS· FATTY AMIDES· HYDROCARBONS· OCTADECANOIDS
· MONOACYLGLYCEROLS· DIACYLGLYCEROLS· TRIACYLGLYCEROLS
· BILE ACIDS· STEROIDS· STEROLS
· CERAMIDES· SPHINGOID BASES· SPHINGOMYELINS
· GLYCEROPHOSPHOCHOLINES PC· GLYCEROPHOSPHOETHANOLAMINES PE· GLYCEROPHOSPHOSERINES PS· GLYCEROPHOSPHOGLYCEROLS PG· GLYCEROPHOSPHOINOSITOLS PI· GLYCEROPHOSPHATES PA
GLYCEROLIPIDSSTEROL LIPIDS
SPHINGOLIPIDS GLYCERO�PHOSPHOLIPIDS
LOOK INSIDE TO LEARN MORE
Fatty Acyls
Mass Spec Standards & Services
GlycerolipidsSphingolipidsGlycerophospholipids
Sterol Lipids
Pages 1-2
Pages 3-4
Page 5
Page 6
Lipidomics 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.
1 WWW.CAYMANCHEM.COMCAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897
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
Fatty AcylsEicosanoids: 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, isoprostanes, thromboxanes, leukotrienes, lipoxins, and hydroperoxy, hydroxy, epoxy, and oxo 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 45 leukotrienes available online
Common hydroxy/hydroperoxy/epoxy/oxo eicosanoids listed, over 180 available online
Common prostaglandins listed, over 425 prostaglandins available online
Common thromboxanes listed, over 20 thromboxanes available online
Hydroxy/Hydroperoxy/Epoxy/Oxo Eicosanoids
Prostaglandins
Thromboxanes
Item No. Product Name
20010 Leukotriene A4 methyl ester
20109 Leukotriene B3
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
Item No. Product Name
18343 (±)5(6)-DiHETE lactone
50651 (±)14(15)-EET
50861 (±)17(18)-EpETE
32550 12(S)-HEPE
32840 (±)18-HEPE
34570 12(S)-HETE
334570 12(S)-HETE-d8
34720 15(S)-HETE
90030 20-HETE
Item No. Product Name
10010 Prostaglandin A1
12010 Prostaglandin D2
14010 Prostaglandin E2
14720 15-keto Prostaglandin E2
14750 16,16-dimethyl Prostaglandin E2
16010 Prostaglandin F2α
16350 8-iso Prostaglandin F2α
17020 Prostaglandin H2
18220 Prostaglandin I2 (sodium salt)
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
19050 2,3-dinor Thromboxane B2
10009584 2,3-dinor Thromboxane B2-d9
19990 Thromboxane B3
19995 11-dehydro Thromboxane B3
Request the full Arachidonic Acid Cascade wall poster at www.caymanchem.com/Literature
To view a complete list of Fatty Acyls,visit us online at www.caymanchem.com
2WWW.CAYMANCHEM.COM CAYMAN CHEMICAL · 1180 EAST ELLSWORTH ROAD · ANN ARBOR, MI 48108 · USA · (800) 364-9897
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 nanomolar concentrations 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
Specialized Pro-Resolving Mediators: An important group of signaling molecules derived from arachidonic acid, eicosapentaenoic acid, docosapentaenoic acid, and docosahexaenoic acid is liberated during the inflammatory process and performs 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 the family of bioactive lipids formed by the conjugation of fatty acids to simple amines such as ethanolamine or monoamine neurotransmitters such as dopamine, taurine, serotonin, or GABA.
Common resolvins listed, more resolvins available online Common maresins listed, more maresins available online
Common essential fatty acids listed, over 300 fatty acids available online
Common lipoxins listed, more lipoxins available online
Resolvins Lipoxins
Essential Fatty Acids
Maresins
Item No. Product Name
10012554 Resolvin D1
13060 17(R)-Resolvin D1
10007279 Resolvin D2
11184 Resolvin D2-d5
13834 Resolvin D3
10007280 Resolvin D5
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
Verified concentration LC-MS identity tested HPLC purity tested Ongoing stability testing
MaxSpec® Quality Guarantee
Request the full Specialized Pro-Resolving Mediators wall poster at www.caymanchem.com/Literature
MAXIMIZE RESULTSMaxSpec® Standards
A line of ready-to-use, quantitative standards prepared specifically for mass spectrometry applications.
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Mass Spectrometry Standards
Mixtures available for · Bioactive Eicosanoids, Precursors, & Metabolites · Hydroxy/Hydroperoxy/Epoxy/Oxo Eicosanoids · Specialized Pro-Resolving Mediators
Prostaglandins Hydroxy/Hydroperoxy/Epoxy/Oxo Eicosanoids
Additional Fatty Acyls
Common prostaglandins and their internal standards listed, over 20 available online
Common hydroxy/hydroperoxy/epoxy/oxo eicosanoids standards listed, over 20 available online
Item No. Product Name
10007202 Prostaglandin D2 MaxSpec® Standard
10007272 Prostaglandin D2-d4 MaxSpec® Standard
10007208 13,14-dihydro-15-keto Prostaglandin D2 MaxSpec® Standard
10007211 Prostaglandin E2 MaxSpec® Standard
10007273 Prostaglandin E2-d4 MaxSpec® Standard
10007214 13,14-dihydro-15-keto Prostaglandin E2 MaxSpec® Standard
25372 13,14-dihydro-15-keto Prostaglandin E2-d4 MaxSpec® Standard
25900 Prostaglandin F1α MaxSpec® Standard
10007219 6-keto Prostaglandin F1α MaxSpec® Standard
10007221 Prostaglandin F2α MaxSpec® Standard
10007275 Prostaglandin F2α-d4 MaxSpec® Standard
Item No. Product Name
10007265 (±)8(9)-DiHET MaxSpec® Standard
10007243 5(S)-HETE MaxSpec® Standard
10007248 12(S)-HETE MaxSpec® Standard
10007269 20-HETE MaxSpec® Standard
Item No. Product Name
10007270 Arachidonoyl Ethanolamide MaxSpec® Standard
10007240 Leukotriene B4 MaxSpec® Standard
10007271 Lipoxin A4 MaxSpec® Standard
10007237 Thromboxane B2 MaxSpec® Standard
Ready-to-Use, Quantitative Standards
Qualitative, Multi-Component LC-MS Mixtures
Achieve quantitative accuracy and interlaboratory reproducibility with Cayman’s new line of MaxSpec® standards and kits for mass spectrometry. MaxSpec®
products are formulated as ready-to-use solutions to accelerate workflows and are guaranteed to meet rigorous quality standards.
Cayman’s fatty acid and eicosanoid mixtures contain 3-20 different compounds and are designed to accelerate workflows and reduce variability. Each mixture undergoes batch-specific LC-MS content analysis and ongoing stability testing to ensure quality.
MaxSpec® Quality GuaranteeVerified concentrationLC-MS identity testedHPLC purity testedOngoing stability testing
· Dietary & Microbiome-Related Fatty Acids · Vasoactive Eicosanoids · Oxidative Stress
Looking to create a custom mass spec mixture? Email us at [email protected]
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Lipidomic Profiling Services
· Eicosanoids · Sphingolipids · Oxidized Phospholipids · Phospholipids (untargeted)
· Project consultation and customized proposal generation · Sample preparation (homogenization, extraction, enrichment as needed) · LC-MS/MS analysis, data collection, and reporting
Maximize Your Data with Customizable Lipid Panels
Service Includes:
Put your lipidomics study in the hands of lipid experts who have decades ofcollective experience in lipid synthesis, purification, and characterization. Cayman’s state-of-the art mass spectrometry laboratories are equipped with high-resolution Orbitrap and triple quadrupole MS, enabling Cayman to offer targeted anduntargeted lipidomics services to meet your specific project needs.
Cayman offers a suite of multiplex lipid panels that offer the sensitivity, efficiency, and specificity needed to identify and quantify biologically relevant lipids.
· Endocannabinoids · Short-Chain Fatty Acids · Cholesterol Esters · Urinary Lipid Metabolites
Cyclooxygenase 5-Lipoxygenase Other Lipoxygenases and P450 Others (Not from AA) Internal Standards
6-keto PGF1α LTB4 5(6)-EET 9-HODE TXB2-d4
TXB2 LTC4 8(9)-EET 13-HODE PGE2-d4
PGF2α LTD4 11(12)-EET 17-HDHA LTD4-d5
PGE2 LTE4 14(15)-EET 18-HEPE LXA4-d5
PGD2 20-hydroxy LTB4 5(6)-DiHET RvD1 LTB4-d4
PGA2 20-carboxy LTB4 8(9)-DiHET RvD2 (±)14(15)-DiHET-d11
PGJ2 5(6)-DiHETE 11(12)-DiHET RvD3 (±)14(15)-EET-d11
15-deoxy-Δ12,14-PGJ2 5-HETE 14(15)-DiHET RvD4 9(S)-HODE-d4
12-HHTrE 5-OxoETE 12-HETE RvE1 5(S)-HETE-d8
11-dehydro TXB2 LXA4 15-HETE MaR1 RvD1-d5
11-HETE LXB4 20-HETE PD1 RvE1-d4
Eicosanoids 44-Plex Panel
Example Panel
Learn more or request a quote at www.caymanchem.com/lipidomics
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LPA�(P2Y5)
LPA�(GPR92, GPR93)
LPA�(P2Y9, GPR23)
G Protein CouplingGq G12/13 Gs Gi
LPA�(EDG-2)
LPA�(EDG-4)
LPA�(EDG-7)
S1P�(EDG-8)
LyPS�(GPR34)
LYSOPHOSPHOLIPID SIGNALING
LPA, LysoPS, and LPI BiosynthesisS1P Biosynthesis
O
O C
O
C
OO
O C
O
C
O
O
O C
O
C
O
Phosphatidic Acid
O
O C
O
C
O
Diacylglycerol
O
OH
O C
O
C
O
Monoacylglycerol
O
OH
OH
C
O
Triacylglycerol
O
O C
O
O C
OC
O
Lysophosphatidic Acid
OH
O C
O
Glycerol-3-phosphate(G3P)
OH
OH
OH
O C
O
OH
O C
O
OH
O C
O
Phosphatidylinositol
O
O C
O
C
O
Lysophosphatidylinositol
OH
O C
O
Galactosylceramide
L-Serine + Palmitoyl-CoA
Dihydroceramide
Ceramide
Sulfogalactosylceramide
HO
NH
O
HO
NH
O
HO
OH
NH
O
HO
OH
NH
O
GlycosphingolipidsComplex
HO
NH
OHO
NH
O
Sphingomyelin
HO
NH
O
Glucosylceramide
HO
OH
NH2
SphingosineSphingosine-1-phosphate
HO
NH2
Ceramide-1-phosphate
HO
NH
O
Lysosphingomyelin
HO
NH2
Phosphoethanolamine
Hexadecanal
H2N
OHC
Functional Groups
GalNAc
Fuc
Sialic acid
Glc
Gal Phosphate
Choline
Serine
Ethanolamine
InositolSulfate
Acyl-CoA
Acyl-CoA
Acyl-CoA
Acyl-CoA
Acyl-CoA
Acyl-CoA
GPAT
Phospholipids
Lysophospholipids
DAGL
MGAT
DGAT
CEPT CEPT
LPP
DAGK
PLA2
LPAAT
PLDCDS
LPEATLPCAT
PLA2
PIS
PLA2 LPIAT
PEMT
PSS1PSS2
PSD
GALC
CGT
GCS
Autotaxin
S1P
LPl
LPA LyPS
GSase
GCase
CDase
SM deacylase
S1P lyase
DES
SMS
CerK
SPT
KDSR
CerS
SK
CerS
C1PP
S1PP
SMase
Cholera ToxinACTIVATES
PLCβ
PLCβ
β γ
Ca2+
Ca2+
Ca2+
β γ
G12/13
Gq
β γ
β γ β γ
IP3
DAG
Adenylate Cyclase
Endoplasmic Reticulum
Ca2+ Channel
GDP GTP
RAP RAP
Epac
cAMP
Pertussis ToxinBLOCKS
ATP
PIP2
PP
P
Ca2+
Ca2+
Ca2+
PKC
PKC
Ca2+Ca2+
Ras
MAPK
Rho
SRF ROCK
Akl Rac
PI3K
LPl
S1P�-�LPA����-�
LyPS������
LPl
S1P-�LPA-�
LyPSLPA�
Gs
Gi
© 2019 Cayman Chemical
LPA-�
S1P���
S1P(EDG-1)
S1P�(EDG-5)
LPl(GPR55)
PKA
LyPS�(GPR174)
Downstream cell-specific responses (e.g., migration, proliferation, survival, cytoskeletal changes)
S1P�(EDG-3)
S1P�(EDG-6)
LyPS�(P2Y10)
LyPS��(A630033H20)
· Glycerolipids · Sphingolipids · GlycerophospholipidsSphingolipids: 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.
Glycerophospholipids: Glycerophospholipids 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. Glycerophospholipids have been widely used to prepare nanoformulations for drug delivery or other types of artificial membranes.
Sphingolipids
Glycerolipids
Glycerophosphocholines (PC) &Glycerophosphoethanolamines (PE)
Platelet-Activating Factors
Item No. Product Name
62527 C6 NBD Ceramide (d18:1/6:0)
10681 C16 Ceramide (d18:1/16:0)
22442 EOS (d18:1/32:1/18:2)
20338 Galactosylsphingosine (d18:1)
10007945 Sphinganine (d18:0)
10007907 Sphingosine (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
10009872 1-Stearoyl-2-Arachidonoyl-d8-sn-Glycero
16489 1,2,3-Triheptadecanoyl-rac-glycerol
Item No. Product Name
15098 1,2-Dioleoyl-sn-glycero-3-PC
15091 1,2-Dioleoyl-sn-glycero-3-PE
10172 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC
10044 PGPC
10031 POV-PC
21139 1-Stearoyl-2-15(S)-HETE-sn-glycero-3-PE
25856 1-Stearoyl-2-15(S)-HpETE-sn-glycero-3-PE
Item No. Product Name
60900 PAF C-16
360900 PAF C-16-d4
60906 Lyso-PAF C-16
60908 Methylcarbamyl PAF C-16
60912 2-O-methyl PAF C-18
60945 2-thio-PAF
Common sphingolipids listed, over 225 sphingolipids available online
Common glycerolipids listed, over 200 glycerolipids available online Over 175 glycerophospholipids available online
Request the full Lysophospholipid Signaling wall poster at www.caymanchem.com/Literature
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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
SteroidsBile Acids
Item No. Product Name
16339 7-keto Cholesterol
10009931 24(S)-hydroxy Cholesterol
11097 25-hydroxy Cholesterol
14790 25(R)-27-hydroxy Cholesterol
Item No. Product Name
15273 Aldosterone
15728 Dehydroepiandrosterone
16146 17α,20β-Dihydroxy-4-pregnen-3-one
10006315 17β-Estradiol
13019 2-Hydroxyestradiol
16145 20-hydroxy Ecdysone
18226 Hydrocortisone 21-hemisuccinate (sodium salt)
10006318 Levonorgestrel
20798 Marinobufagenin
10006317 Mifepristone
10008519 6β-hydroxy Testosterone
Item No. Product Name
10011286 Chenodeoxycholic Acid
20250 Cholic Acid
9002532 Cholic Acid 7-sulfate
16942 Glycochenodeoxycholic Acid (sodium salt)
22670 Glycohyocholic Acid
21723 Glycolithocholic Acid
20253 Lithocholic Acid
20291 α-Muricholic Acid
20287 β-Muricholic Acid
20290 Murideoxycholic Acid
20275 Taurochenodeoxycholic Acid (sodium salt)
16215 Taurocholic Acid (sodium salt)
9002538 Taurocholic Acid 3-sulfate
15935 Taurodeoxycholic Acid (sodium salt)
22669 Taurohyocholic Acid
17275 Taurolithocholic Acid (sodium salt)
20277 Tauroursodeoxycholic Acid
15121 Ursodeoxycholic acid (sodium salt)
Common oxysterols listed, over 30 oxysterols available onlineCommon bile acids listed, over 25 bile acids and their internal standards available online
Common steroids listed, over 200 steroids available online
Custom Synthesis SpotlightWhen 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
Request a quote for a custom synthesis of your particular lipidat www.caymanchem.com/chemicalsynthesis
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CONTACT US
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FAX: (734) 971-3640
WEB: www.caymanchem.com
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ADDRESS: 1180 E. Ellsworth Rd. · Ann Arbor, MI · 48108 · USA