H9521

Sigma-Aldrich

15(S)-Hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid

~100 μg/mL in ethanol, ≥95%

Synonym(s):
15(S)-HPETE
Empirical Formula (Hill Notation):
C20H32O4
CAS Number:
Molecular Weight:
336.47
EC Number:
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

assay

≥95%

concentration

~100 μg/mL in ethanol

shipped in

dry ice

storage temp.

−70°C

SMILES string

CCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI

1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

InChI key

BFWYTORDSFIVKP-VAEKSGALSA-N

Packaging

Packaged under Argon.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

F

Risk Statement

11

Safety Statement

7-16

RIDADR

UN1170 - class 3 - PG 2 - Ethanol, solution

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
J A Weaver et al.
Free radical biology & medicine, 30(3), 299-308 (2001-02-13)
Selenium (Se) is an integral component of glutathione peroxidase and is able to detoxify peroxides that can affect arachidonic acid (AA) metabolism, thereby influencing eicosanoid biosynthesis. This study investigated the effects of oxidant stress, a consequence of Se deficiency, on...
Lorraine M Sordillo et al.
Free radical biology & medicine, 44(1), 34-43 (2007-11-30)
Increased intracellular adhesion molecule 1 (ICAM-1) expression and enhanced monocyte recruitment to the endothelium are critical steps in the early development of atherosclerosis. The 15-lipoxygenase 1 (15-LOX1) pathway can generate several proinflammatory eicosanoids that are known to enhance ICAM-1 expression...
Kotha Anil Kumar et al.
Biotechnology and applied biochemistry, 52(Pt 2), 121-133 (2008-05-23)
The antiproliferative effects of 15-LOX (15-lipoxygenase) metabolites of arachidonic acid {(15S)-HPETE [(15S)-hydroperoxyeicosatetraenoic acid] and (15S)-HETE [(15S)-hydroxyeicosatetraenoic acid]} and the mechanism(s) involved were studied in the human T-cell leukaemia cell line Jurkat. (15S)-HPETE, the hydroperoxy metabolite of 15-LOX, inhibited the growth...
Nguyen Dang Hung et al.
Prostaglandins & other lipid mediators, 90(3-4), 105-111 (2009-10-13)
Arachidonic acid, released from PLA(2) hydrolysis of phosphatidylcholine, is converted to pro-inflammatory or anti-inflammatory mediators. Although lysophosphatidylcholine (lysoPC), another product, is known to be pro-inflammatory, the role of polyunsaturated lysoPCs is not clear. Here, we examined the role of arachidonoyl-lysoPC...
Huiyong Yin et al.
Antioxidants & redox signaling, 7(1-2), 170-184 (2005-01-15)
Free radical-initiated autoxidation of polyunsaturated fatty acids (PUFAs) has been implicated in numerous human diseases, including atherosclerosis and cancer. This review covers the free radical mechanisms of lipid oxidation and recent developments of analytical techniques to analyze the lipid oxidation...

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