All Photos(1)
Synonym(s):
Ethyl (3S)-3-hydroxybutanoate
Linear Formula:
CH3CH(OH)CH2CO2C2H5
CAS Number:
Molecular Weight:
132.16
Beilstein:
2347951
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
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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.
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.
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Certificates of Analysis (COA)
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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)
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