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E4765

Sigma-Aldrich

trans-9,10-Epoxystearic acid

~99% (capillary GC)

Synonym(s):

trans-9,10-Epoxyoctadecanoic acid

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About This Item

Empirical Formula (Hill Notation):
C18H34O3
CAS Number:
2443-39-2
Molecular Weight:
298.46
EC Number:
219-477-3
MDL number:
MFCD00133868
UNSPSC Code:
12352211
PubChem Substance ID:
24894580

Assay

~99% (capillary GC)

form

solid

functional group

carboxylic acid
epoxy

shipped in

ambient

storage temp.

−20°C

SMILES string

CCCCCCCCC1OC1CCCCCCCC(O)=O

InChI

1S/C18H34O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h16-17H,2-15H2,1H3,(H,19,20)

InChI key

IMYZYCNQZDBZBQ-UHFFFAOYSA-N

Packaging

Sealed ampule

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
081H8464

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F Pinot et al.
Biochemical and biophysical research communications, 184(1), 183-193 (1992-04-15)
A microsomal fraction from etiolated Vicia sativa seedlings incubated aerobically with [1-14C]oleic acid (Z9-octadecenoic acid) or [1-14C]9,10-epoxystearic acid or [1-14C]9,10-dihydroxystearic acid catalyzed the NADPH-dependent formation of hydroxylated metabolites. The chemical structure of compounds formed from oleic, 9,10-epoxystearic or 9,10-dihydroxystearic acids
P Fahlstadius
Lipids, 23(11), 1015-1018 (1988-11-01)
Racemic cis-9,10-epoxystearic acid was isolated from total lipids of human leukocytes. Identification of the epoxy acid was based mainly on gas liquid chromatographic-mass spectrometric analysis and on its chemical conversion into threo-9,10-dihydroxystearic acid. A mass spectrometric method for quantitative determination
Determination of 9,10-epoxystearate ester in intravenous solutions stored in poly(vinyl chloride) bags, using gas chromatography-single-ion monitoring mass spectrometry.
G A Ulsaker et al.
The Analyst, 109(7), 967-968 (1984-07-01)
E Blée et al.
The Journal of biological chemistry, 267(17), 11881-11887 (1992-06-15)
Soluble epoxide hydrolase purified from soybean catalyzes trans-addition of water across the oxirane ring of cis-9,10-epoxystearic acid with inversion of configuration at the attacked carbon, yielding threo-9,10-dihydroxystearic acid. Kinetic analyses of the progress curves, obtained at low substrate concentrations (i.e.
F Müller et al.
European journal of biochemistry, 245(2), 490-496 (1997-04-15)
Mammalian soluble and microsomal epoxide hydrolases have been proposed to belong to the family of alpha/beta-hydrolase-fold enzymes. These enzymes hydrolyse their substrates by a catalytic triad, with the first step of the enzymatic reaction being the formation of a covalent
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