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00878

Sigma-Aldrich

(±)-2-Acetoxypropionic acid

≥97.0% (GC)

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Linear Formula:
CH3COOCH(CH3)COOH
CAS Number:
Molecular Weight:
132.11
Beilstein:
1722938
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥97.0% (GC)

refractive index

n20/D 1.423

density

1.176 g/mL at 20 °C (lit.)

SMILES string

CC(OC(C)=O)C(O)=O

InChI

1S/C5H8O4/c1-3(5(7)8)9-4(2)6/h3H,1-2H3,(H,7,8)

InChI key

WTLNOANVTIKPEE-UHFFFAOYSA-N

Related Categories

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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H S Park et al.
Biochimica et biophysica acta, 1245(3), 366-370 (1995-12-14)
Acetolactate nonenzymatically reduced flavins, quinones and nicotinamide coenzymes in a time-dependent manner at physiological pH and moderate temperature. In the presence of excess acetolactate, the reduction of FAD and NAD+ followed pseudo-first-order kinetics. The rate of reduction was proportional to
C T Duong et al.
Metabolic engineering, 13(6), 638-647 (2011-08-10)
Diacetyl causes an unwanted buttery off-flavor in lager beer. It is spontaneously generated from α-acetolactate, an intermediate of yeast's valine biosynthesis released during the main beer fermentation. Green lager beer has to undergo a maturation process lasting two to three
N Goupil-Feuillerat et al.
Journal of bacteriology, 179(20), 6285-6293 (1997-10-23)
The alpha-acetolactate decarboxylase gene aldB is clustered with the genes for the branched-chain amino acids (BCAA) in Lactococcus lactis subsp. lactis. It can be transcribed with BCAA genes under isoleucine regulation or independently of BCAA synthesis under the control of
E A Sergienko et al.
Biochemistry, 40(25), 7369-7381 (2001-06-20)
Yeast pyruvate decarboxylase (YPDC), in addition to forming its metabolic product acetaldehyde, can also carry out carboligase reactions in which the central enamine intermediate reacts with acetaldehyde or pyruvate (instead of the usual proton electrophile), resulting in the formation of
Ahmet Baykal et al.
Bioorganic chemistry, 34(6), 380-393 (2006-11-07)
In addition to the decarboxylation of 2-oxo acids, thiamin diphosphate (ThDP)-dependent decarboxylases/dehydrogenases can also carry out so-called carboligation reactions, where the central ThDP-bound enamine intermediate reacts with electrophilic substrates. For example, the enzyme yeast pyruvate decarboxylase (YPDC, from Saccharomyces cerevisiae)

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