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311111

Sigma-Aldrich

Methyl oleate

99%

Synonym(s):

Methyl cis-9-octadecenoate, Oleic acid methyl ester

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About This Item

Linear Formula:
CH3(CH2)7CH=CH(CH2)7CO2CH3
CAS Number:
112-62-9
Molecular Weight:
296.49
Beilstein:
1727037
EC Number:
203-992-5
MDL number:
MFCD00009578
UNSPSC Code:
12352100
PubChem Substance ID:
24858840
NACRES:
NA.22

vapor pressure

10 mmHg ( 205 °C)

Quality Level

200

Assay

99%

form

liquid

refractive index

n20/D 1.452 (lit.)

bp

218 °C/20 mmHg (lit.)

density

0.874 g/mL at 20 °C (lit.)

functional group

ester

storage temp.

−20°C

SMILES string

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

InChI

1S/C19H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h10-11H,3-9,12-18H2,1-2H3/b11-10-

InChI key

QYDYPVFESGNLHU-KHPPLWFESA-N

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General description

The methyl oleate monolayers at the air-water interface undergoes ozonolysis that results in rapid loss of material through cleavage of the C=C bond and evaporation/dissolution of reaction products.

Application

Methyl oleate can be used as a reactant to synthesize:
  • Epoxidized methyl oleate via epoxidation.
  • Allyl azides via manganese(III) acetate-mediated addition of azide in the alkyl chain.
  • Bromohydrin products via hydroxybromination with N-bromosuccinimide.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR0129
MKCQ9668
MKCQ6509
MKCQ1723
MKCP8588

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In Saccharomyces cerevisiae, acyl-coenzyme A desaturation by Ole1 requires molecular oxygen. Tween 80, a poly-ethoxylated sorbitan-oleate ester, is therefore routinely included in anaerobic growth media as a source of unsaturated fatty acids (UFAs). During optimization of protocols for anaerobic bioreactor
Estefania Oliva et al.
Biomolecules, 10(2) (2020-02-26)
Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions
Tatiana R Amarante et al.
Inorganic chemistry, 52(8), 4618-4628 (2013-03-28)
The reaction of MoO3, 2,2'-bipyridine-5,5-dicarboxylic acid (H2bpdc), water, and dimethylformamide in the mole ratio 1:1:1730:130 at 150 °C for 3 days in a rotating Teflon-lined digestion bomb leads to the isolation of the molybdenum oxide/bipyridinedicarboxylate hybrid material (DMA)[MoO3(Hbpdc)]·nH2O (1) (DMA
Christian Pfrang et al.
Physical chemistry chemical physics : PCCP, 16(26), 13220-13228 (2014-05-30)
Ozonolysis of methyl oleate monolayers at the air-water interface results in surprisingly rapid loss of material through cleavage of the C=C bond and evaporation/dissolution of reaction products. We determine using neutron reflectometry a rate coefficient of (5.7 ± 0.9) ×
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