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Sigma-Aldrich

Ethyl (R)-(−)-3-hydroxybutyrate

98%

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About This Item

Linear Formula:
CH3CH(OH)CH2CO2C2H5
CAS Number:
24915-95-5
Molecular Weight:
132.16
MDL number:
MFCD00075386
UNSPSC Code:
12352108
PubChem Substance ID:
24861478
NACRES:
NA.22

Assay

98%

form

liquid

optical activity

[α]20/D −46°, c = 1 in chloroform

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.42 (lit.)

bp

75-76 °C/12 mmHg (lit.)

density

1.017 g/mL at 25 °C (lit.)

functional group

ester
hydroxyl

SMILES string

CCOC(=O)C[C@@H](C)O

InChI

1S/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3/t5-/m1/s1

InChI key

OMSUIQOIVADKIM-RXMQYKEDSA-N

Related Categories

General description

Ethyl (R)-(-)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds used in the pharmaceutical industry. It is formed during the hydrolysis of poly-3-hydroxybutyrate.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

147.2 °F - closed cup

Flash Point(C)

64 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0753
MKCS0020
MKCP7772
MKCF8743
MKBT8969V

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A two-step enzymatic resolution process for large-scale production of (S)-and (R)-ethyl-3-hydroxybutyrate.
Fishman A, et al.
Biotechnology and Bioengineering, 74(3), 256-263 (2001)
Young-Min Han et al.
Molecular cell, 71(6), 1064-1078 (2018-09-11)
β-hydroxybutyrate (β-HB) elevation during fasting or caloric restriction is believed to induce anti-aging effects and alleviate aging-related neurodegeneration. However, whether β-HB alters the senescence pathway in vascular cells remains unknown. Here we report that β-HB promotes vascular cell quiescence, which
Xiao-Hong Chen et al.
PloS one, 9(4), e94543-e94543 (2014-04-18)
A novel carbonyl reductase (AcCR) catalyzing the asymmetric reduction of ketones to enantiopure alcohols with anti-Prelog stereoselectivity was found in Acetobacter sp. CCTCC M209061 and enriched 27.5-fold with an overall yield of 0.4% by purification. The enzyme showed a homotetrameric

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