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Merck
CN

M9190

Methyl 14(S),15(S)-epoxy-11(R,S)-hydroxy-(5Z,8Z,12E)-eicosatrienoate

≥95% (HPLC), hexane solution

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About This Item

Empirical Formula (Hill Notation):
C21H34O4
Molecular Weight:
350.49
NACRES:
NA.25
PubChem Substance ID:
329818087
UNSPSC Code:
12352211
EC Number:
203-777-6
MDL number:
MFCD04040012

Key Documents

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InChI

1S/C21H34O4/c1-3-4-10-14-19-20(25-19)17-16-18(22)13-11-8-6-5-7-9-12-15-21(23)24-2/h5,7-8,11,16-20,22H,3-4,6,9-10,12-15H2,1-2H3/b7-5-,11-8-,17-16+/t18?,19-,20-/m0/s1

InChI key

MHXSCMMMTRMMBI-PUWVHZPJSA-N

SMILES string

CCCCCC1O[C@H]1\C=C\C(O)C\C=C/C\C=C/CCCC(=O)OC

assay

≥95% (HPLC)

form

hexane solution

functional group

ester

lipid type

unsaturated FAs

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

Application

Methyl 14(S),15(S)-epoxy-11(R,S)-hydroxy-(5Z,8Z,12E)-eicosatrienoate may be used as a reference material in the analysis and identification of 15-lipoxygenase metabolites.

Other Notes

15-Lipoxygenase product of arachidonic acid, formed by a similar biosynthesis as hepoxilins.

signalword

Danger

Hazard Classifications

Aquatic Chronic 2 - Asp. Tox. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 Inhalation - STOT SE 3

target_organs

Central nervous system, Nervous system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

-14.8 °F - closed cup

flash_point_c

-26 °C - closed cup

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
052K1452

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Nitin T Aggarwal et al.
Vascular pharmacology, 56(1-2), 106-112 (2011-12-27)
Endothelial 15-lipoxygenase-1 (15-LO-1) metabolites of arachidonic acid (AA), 11,12,15-trihydroxyeicosatrienoic acid (THETA) and 15-hydroxy-11,12-epoxyeicosatrienoic acid (HEETA) and nitric oxide (NO) mediate relaxations to acetylcholine (ACH). However, interactions between NO and the 15-LO-1 pathway have not been explored. Therefore, the effect of
S Bhattacharya et al.
Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine, 30(4), 185-199 (2009-09-16)
Enzymes involved in the oxidative metabolism of n-6 polyunsaturated fatty acids, like lipoxygenase (LOX) and cyclooxygenase (COX), are significant in the pathogenesis of colorectal cancer. Of these enzymes, 15-LOX-1 is expressed in colon. Aim of this article is to describe
Sasikumar J Soumya et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 61(7), 707-718 (2012-03-28)
15(S)-Hydroxyeicosatetraenoic acid [15(S)-HETE] and 15(S)-hydroperoxyeicosatetraenoic acid [15(S)-HPETE] are the products of arachidonic acid formed in the 15-lipoxygenase pathway. They have opposing effects on the inflammatory process. The present study was designed to examine the role of these metabolites on angiogenesis

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