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:

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

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
Suraneni V K Mahipal et al.
Biochemical pharmacology, 74(2), 202-214 (2007-05-23)
Growth inhibitory effects of 15-lipoxygenase-1 [13-(S)-HPODE and 13-(S)-HODE] and 15-lipoxygenase-2 [15-(S)-HPETE and 15-(S)-HETE] (15-LOX-1 and LOX-2) metabolites and the underlying mechanisms were studied on chronic myeloid leukemia cell line (K-562). The hydroperoxy metabolites, 15-(S)-HPETE and 13-(S)-HPODE rapidly inhibited the growth...
Lorraine M Sordillo et al.
Prostaglandins & other lipid mediators, 76(1-4), 19-34 (2005-06-22)
Oxidant stress plays an important role in the etiology of vascular diseases by increasing rates of endothelial cell apoptosis, but few data exist on the mechanisms involved. Using a unique model of oxidative stress based on selenium deficiency (-Se), the...
Judith V Ferrante et al.
Journal of immunology (Baltimore, Md. : 1950), 174(6), 3169-3172 (2005-03-08)
The metabolism of arachidonic acid via the lipoxygenase and cyclooxygenase pathways generates metabolites that regulate the inflammatory response. Although products of lipoxygenase are classically proinflammatory, recently it has been demonstrated that lipoxins, 15-hydroperoxyeicosatetraenoic acid (15-HPETE) and 15-hydroxyeicosatetraenoic acid exhibit anti-inflammatory...
Gang Wu et al.
Biochemistry, 46(2), 534-542 (2007-01-11)
Prostaglandin H synthase-1 (PGHS-1) is a bifunctional heme protein catalyzing both a peroxidase reaction, in which peroxides are converted to alcohols, and a cyclooxygenase reaction, in which arachidonic acid is converted into prostaglandin G2. Reaction of PGHS-1 with peroxide forms...
Colleen Rock et al.
Prostaglandins, leukotrienes, and essential fatty acids, 83(4-6), 203-210 (2010-09-10)
Reactive lipid hydroperoxides formed by lipoxygenases and cyclooxygenases can contribute to disease through cellular oxidative damage. Several selenoproteins have lipid hydroperoxidase activity, including glutathione peroxidase 4, thioredoxin reductase, and selenoprotein P (SelP). SelP is an extracellular glycoprotein that functions both...

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