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Ethyl (S)-3-hydroxybutyrate

Name: Ethyl (<I>S</I>)-3-hydroxybutyrate
Brand: ALDRICH

99%

Synonym(s):

Ethyl (3S)-3-hydroxybutanoate

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About This Item

Linear Formula:

CH₃CH(OH)CH₂CO₂C₂H₅

CAS Number:

56816-01-4

Molecular Weight:

132.16

UNSPSC Code:

12352108

NACRES:

NA.22

PubChem Substance ID:

24863329

EC Number:

260-393-1

Beilstein/REAXYS Number:

2347951

MDL number:

MFCD00066206

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Properties

assay

99%

form

liquid

optical activity

[α]20/D +43°, c = 1 in chloroform

optical purity

ee: 94% (GLC)

refractive index

n20/D 1.421 (lit.)

bp

180-182 °C (lit.)

density

1.012 g/mL at 20 °C (lit.)

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-/m0/s1

InChI key

OMSUIQOIVADKIM-YFKPBYRVSA-N

Description

General description

Ethyl (S)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds such as pheromones and carbapenem antibiotics.

Application

Ethyl (S)-3-hydroxybutyrate may be used in the preparation of 3-(1′-hydroxyethyl)-2-azetidinones.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

147.2 °F - closed cup

flash_point_c

64 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Asymmetric synthesis of (1'R, 3R, 4R)-4-acetoxy-3-[1'-((tert-butyldimethylsilyl) oxy) ethyl]-2-azetidinone and other 3-(1'-hydroxyethyl)-2-azetidinones from (S)-(+)-ethyl 3-hydroxybutanoate: formal total synthesis of (+)-thienamycin.

Journal of the American Chemical Society, 109(4), 1129-1135 (1987)

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)