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Sigma-Aldrich

Oleoyl chloride

≥89%

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Synonym(s):
(9Z)-9-Octadecenoyl chloride, (Z)-9-Octadecenoyl chloride, 9-(Z)-Octadecen-1-oyl chloride, Oleic acid chloride, Oleic chloride, Oleyl chloride, cis-9-Octadecenoyl chloride
Linear Formula:
CH3(CH2)7CH=CH(CH2)7COCl
CAS Number:
112-77-6
Molecular Weight:
300.91
Beilstein:
1211748
EC Number:
204-005-0
MDL number:
MFCD00134332
UNSPSC Code:
12352100
PubChem Substance ID:
24862853
NACRES:
NA.22

Quality Level

200

Assay

≥89%

form

liquid

refractive index

n20/D 1.463 (lit.)

bp

193 °C/4 mmHg (lit.)

density

0.91 g/mL at 25 °C (lit.)

SMILES string

CCCCCCCC\C=C/CCCCCCCC(Cl)=O

InChI

1S/C18H33ClO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3/b10-9-

InChI key

MLQBTMWHIOYKKC-KTKRTIGZSA-N

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General description

Oleoyl chloride is a fatty acid derivative.

Application

Oleoyl chloride may be used:
  • in the chemical modification of the jute fibbers to confer hydrophobicity and resistance to biofibers
  • in the synthesis of Oleoyl-S-lipoate, via reaction with dihydrolipoate
  • in the preparation of symmetrical triglyceride, 2-oleoyl distearin
  • in the preparation of ergosteryl oleate

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

339.8 °F

Flash Point(C)

171 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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The specificity of pancreatic lipase for the primary hydroxyl groups of glycerides.
F H MATTSON et al.
The Journal of biological chemistry, 219(2), 735-740 (1956-04-01)
K Ohta et al.
Applied and environmental microbiology, 46(4), 821-825 (1983-10-01)
An exogenous ternary complex composed of Tween 80, ergosterol, and albumin increased the final ethanol concentration of fermentation by sake yeasts from 17.2 to 19.0% (vol/vol) and reduced the fermentation time from 30 to 25 days. Likewise, a complex of
D E Griffiths
The Biochemical journal, 160(3), 809-812 (1976-12-15)
ATP synthase preparations [complex V, proton-translocatin ATPase (adenosine triphosphatase) and oligomycin-sensitive ATPase ] contain stoicheiometric amounts of lipoic acid residues (up to 6mol of lipoic acid/mol of ATPase complex) and catalyse net ATP synthesis in an uncoupler-and oligomycin-sensitive reaction utilizing
F Corrales et al.
Journal of hazardous materials, 144(3), 730-735 (2007-02-27)
Natural fiber reinforced composites is an emerging area in polymer science. Fibers derived from annual plants are considered a potential substitute for non-renewable synthetic fibers like glass and carbon fibers. The hydrophilic nature of natural fibers affects negatively its adhesion
Noemi Jiménez-Rojo et al.
Current biology : CB, 30(19), 3775-3787 (2020-08-29)
Sphingolipids play important roles in physiology and cell biology, but a systematic examination of their functions is lacking. We performed a genome-wide CRISPRi screen in sphingolipid-depleted human cells and identified hypersensitive mutants in genes of membrane trafficking and lipid biosynthesis
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