Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

M9190

Sigma-Aldrich

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

≥95% (HPLC), hexane solution

Sign Into View Organizational & Contract Pricing


About This Item

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

Quality Level

assay

≥95% (HPLC)

form

hexane solution

functional group

ester

lipid type

unsaturated FAs

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

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

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_germany

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


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service