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H9521

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

Name: 15(S)-Hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid
Brand: SIGMA

~100 μg/mL in ethanol, ≥95%

Synonym(s):

15(S)-HPETE

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₃₂O₄

CAS Number:

70981-96-3

Molecular Weight:

336.47

UNSPSC Code:

12352200

PubChem Substance ID:

24895857

EC Number:

200-578-6

MDL number:

MFCD00063577

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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

GHS02,GHS07

signalword

Danger

hcodes

H225,H319

pcodes

P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

57.2 °F - closed cup

flash_point_c

14 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品

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Effects of (15S)-hydroperoxyeicosatetraenoic acid and (15S)-hydroxyeicosatetraenoic acid on the acute- lymphoblastic-leukaemia cell line Jurkat: activation of the Fas-mediated death pathway.

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

Effect of 15-lipoxygenase metabolites, 15-(S)-HPETE and 15-(S)-HETE on chronic myelogenous leukemia cell line K-562: reactive oxygen species (ROS) mediate caspase-dependent apoptosis.

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

Novel role of lipoxygenases in the inflammatory response: promotion of TNF mRNA decay by 15-hydroperoxyeicosatetraenoic acid in a monocytic cell line.

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

Lipid peroxidation scavengers prevent the carbonylation of cytoskeletal brain proteins induced by glutathione depletion.

Oscar A Bizzozero et al.

Neurochemical research, 32(12), 2114-2122 (2007-06-07)

In this study, we investigated the possible link between lipid peroxidation (LPO) and the formation of protein carbonyls (PCOs) during depletion of brain glutathione (GSH). To this end, rat brain slices were incubated with the GSH depletor diethyl maleate (DEM)

Liquid chromatography/mass spectrometry analysis of bifunctional electrophiles and DNA adducts from vitamin C mediated decomposition of 15-hydroperoxyeicosatetraenoic acid.

Michelle V Williams et al.

Rapid communications in mass spectrometry : RCM, 19(6), 849-858 (2005-02-22)

Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into 15-hydroperoxy-5,8,11,13-(Z,Z,ZE)-eicosatetraenoic acid (15-HPETE). Cyclooxygenases and lipoxygenases can also convert arachidonic acid into 15-HPETE. Vitamin C mediated decomposition of 15(S)-HPETE to protein- and DNA-reactive bifunctional electrophiles was examined by

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