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About This Item
Linear Formula:
CH3CH(OH)CH2CO2C2H5
CAS Number:
Molecular Weight:
132.16
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
EC Number:
260-393-1
Beilstein/REAXYS Number:
2347951
MDL number:
Product Name
Ethyl (S)-3-hydroxybutyrate, 99%
InChI key
OMSUIQOIVADKIM-YFKPBYRVSA-N
InChI
1S/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3/t5-/m0/s1
SMILES string
CCOC(=O)C[C@H](C)O
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.)
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Application
Ethyl (S)-3-hydroxybutyrate may be used in the preparation of 3-(1′-hydroxyethyl)-2-azetidinones.
General description
Ethyl (S)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds such as pheromones and carbapenem antibiotics.
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
Regulatory Information
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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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