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220396

Sigma-Aldrich

Ethyl 2-acetoxy-2-methylacetoacetate

97%

Synonym(s):

Ethyl 2-acetyllactate acetate

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About This Item

Linear Formula:
CH3COC(O2CCH3)(CH3)CO2C2H5
CAS Number:
25409-39-6
Molecular Weight:
202.20
EC Number:
246-951-7
MDL number:
MFCD00009127
UNSPSC Code:
12352100
PubChem Substance ID:
24852957

assay

97%

form

liquid

refractive index

n20/D 1.428 (lit.)

bp

80-84 °C/1 mmHg (lit.)

density

1.079 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C(C)(OC(C)=O)C(C)=O

InChI

1S/C9H14O5/c1-5-13-8(12)9(4,6(2)10)14-7(3)11/h5H2,1-4H3

InChI key

RHFWCEYBHLGCKH-UHFFFAOYSA-N

Application

Ethyl 2-acetoxy-2-methylacetoacetate was used to prepare 2-acetolactate via hydrolysis with NaOH. It was also used in isolation and characterization of a novel thermophilic bacterium Geobacillus sp. for the production of acetoin and 2,3-butanediol.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

219.2 °F - closed cup

flash_point_c

104.00 °C - closed cup

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

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Zijun Xiao et al.
Biotechnology for biofuels, 5(1), 88-88 (2012-12-12)
Acetoin and 2,3-butanediol are two important biorefinery platform chemicals. They are currently fermented below 40°C using mesophilic strains, but the processes often suffer from bacterial contamination. This work reports the isolation and identification of a novel aerobic Geobacillus strain XT15
Lingxue Lu et al.
Microbial cell factories, 19(1), 102-102 (2020-05-14)
Acetoin, especially the optically pure (3S)- or (3R)-enantiomer, is a high-value-added bio-based platform chemical and important potential pharmaceutical intermediate. Over the past decades, intense efforts have been devoted to the production of acetoin through green biotechniques. However, efficient and economical
Chin-Yu Chen et al.
Scientific reports, 8(1), 7176-7176 (2018-05-10)
Ketol-acid reductoisomerase (KARI) is a bifunctional enzyme in the second step of branched-chain amino acids biosynthetic pathway. Most KARIs prefer NADPH as a cofactor. However, KARI with a preference for NADH is desirable in industrial applications including anaerobic fermentation for
R Y Xing et al.
Journal of bacteriology, 173(6), 2086-2092 (1991-03-01)
Methanococcus aeolicus, Methanococcus maripaludis, and Methanococcus voltae contain similar levels of four enzymes of branched-chain amino acid biosynthesis: acetohydroxy acid synthase, acetohydroxy acid isomeroreductase, dihydroxy acid dehydratase, and transaminase B. Following growth at low partial pressures of H2-CO2, the levels

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