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Merck
CN

83916

Methyl ricinoleate

analytical standard

Synonym(s):

(R)-12-Hydroxy-cis-9-octadecenoic acid methyl ester, Methyl 12-hydroxyoleate, Ricinoleic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C19H36O3
CAS Number:
141-24-2
Molecular Weight:
312.49
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329769092
EC Number:
205-472-3
Beilstein/REAXYS Number:
6132055
MDL number:
MFCD00046712

Key Documents

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Product Name

Methyl ricinoleate, analytical standard

InChI key

XKGDWZQXVZSXAO-ADYSOMBNSA-N

InChI

1S/C19H36O3/c1-3-4-5-12-15-18(20)16-13-10-8-6-7-9-11-14-17-19(21)22-2/h10,13,18,20H,3-9,11-12,14-17H2,1-2H3/b13-10-/t18-/m1/s1

SMILES string

O=C(OC)CCCCCCC/C=C\C[C@H](O)CCCCCC

grade

analytical standard

assay

≥99.0% (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

format

neat

functional group

ester

shipped in

ambient

storage temp.

−20°C

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

General description

Methyl ricinoleate is an enantiomerically renewable compound commercially obtained by the transesterification from castor oil, commonly used in cosmetics, plasticizers, lubricating oils and fine-chemical industries.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP0920
BCCN1720
BCCK2128
BCCG7281
BCCF3844

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Synthesis of Enantiomerically Pure 2, 3, 4, 6-Tetrasubstituted Tetrahydropyrans by Prins-Type Cyclization of Methyl Ricinoleate and Aldehydes.
Biermann U, et al.
European Journal of Organic Chemistry, 2006(11), 2631-2637 (2006)
Y Waché et al.
Applied and environmental microbiology, 67(12), 5700-5704 (2001-11-28)
Some microorganisms can transform methyl ricinoleate into gamma-decalactone, a valuable aroma compound, but yields of the bioconversion are low due to (i) incomplete conversion of ricinoleate (C(18)) to the C(10) precursor of gamma-decalactone, (ii) accumulation of other lactones (3-hydroxy-gamma-decalactone and
A Endrizzi et al.
Journal of basic microbiology, 35(5), 285-292 (1995-01-01)
The capacity of several strains of yeasts to do the bioconversion of methyl ricinoleate into gamma-decalactone, was studied in a medium containing this methylic ester of fatty acid as sole carbon source. Amongst the strains which are able to do
Optimization of methyl ricinoleate synthesis with ionic liquids as catalysts using the response surface methodology.
Xu W, et al.
Chemical Engineering Journal, 275(11), 63-70 (2015)
G Feron et al.
FEMS microbiology letters, 149(1), 17-24 (1997-04-01)
This paper provides new information about the metabolism of various fatty acids and gamma-decalactone production by yeast. An analysis of the fatty acid composition of the yeast Sporidiobolus salmonicolor during batch production of lactone with ricinoleic acid methyl ester as
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