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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
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
Alejandro González-Benjumea et al.
Frontiers in bioengineering and biotechnology, 8, 605854-605854 (2021-01-21)
Epoxides of vegetable oils and free and methylated fatty acids are of interest for several industrial applications. In the present work, refined rapeseed, sunflower, soybean, and linseed oils, with very different profiles of mono- and poly-unsaturated fatty acids, were saponified
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