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374709

Sigma-Aldrich

Ethyl (S)-3-hydroxybutyrate

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
Beilstein:
2347951
EC Number:
260-393-1
MDL number:
MFCD00066206
UNSPSC Code:
12352108
PubChem Substance ID:
24863329
NACRES:
NA.22

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

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General description

Ethyl (S)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds such as pheromones and carbapenem antibiotics.[1]

Application

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

147.2 °F - closed cup

Flash Point(C)

64 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

374709-BULK:
374709-5ML:
374709-250MG:
374709-VAR:
374709-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCBM4473V
1384419V
1384419
1199802
S33374

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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)
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)

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