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338125

Sigma-Aldrich

(R)-(−)-Glycidyl butyrate

96%

Synonym(s):

(R)-(−)-Oxirane-2-methanol butyrate

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About This Item

Empirical Formula (Hill Notation):
C7H12O3
CAS Number:
60456-26-0
Molecular Weight:
144.17
Beilstein/REAXYS Number:
5246881
MDL number:
MFCD00075120
UNSPSC Code:
12352005
PubChem Substance ID:
24860520
NACRES:
NA.22

Quality Level

100

assay

96%

form

liquid

optical activity

[α]25/D −31°, neat

refractive index

n20/D 1.428 (lit.)

bp

197 °C (lit.)

density

1.032 g/mL at 20 °C (lit.)

SMILES string

CCCC(=O)OC[C@H]1CO1

InChI

1S/C7H12O3/c1-2-3-7(8)10-5-6-4-9-6/h6H,2-5H2,1H3/t6-/m1/s1

Inchi Key

YLNSNVGRSIOCEU-ZCFIWIBFSA-N

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Application

(R)-(-)-glycidyl butyrate undergoes hydrolysis in the presence of lipase enzyme to form (S)-(-)-glycidol. It may also be used to synthesize 1-butyroyl 2-oleoyl-3-bromo-sn-glycerol and (R)-3-(dibenzo[b,e][1,4]dioxin-7-yl)-5-(hydroxymethyl)oxazolidin-2-one.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

183.2 °F - closed cup

flash_point_c

84 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Synthesis of enantiomerically pure glycidol via a fully enantioselective lipase-catalyzed resolution.
Palomo JM, et al.
Tetrahedron Asymmetry, 16(4), 869-874 (2005)
Chiral synthesis of a triglyceride: example of 1-butyroyl 2-oleoyl 3-palmitoyl sn glycerol.
Villeneuve P, et al.
Chemistry and Physics of Lipids, 72(2), 135-141 (1994)
Synthesis of novel oxazolidinone antimicrobial agents.
Ebner DC, et al.
Bioorganic & Medicinal Chemistry, 16(5), 2651-2656 (2008)
Arnaldo Glogauer et al.
Microbial cell factories, 10, 54-54 (2011-07-19)
Metagenomics, the application of molecular genomics to consortia of non-cultivated microbes, has the potential to have a substantial impact on the search for novel industrial enzymes such as esterases (carboxyl ester hydrolases, EC 3.1.1.1) and lipases (triacylglycerol lipases, EC 3.1.1.3).

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