56655
(−)-Methyl (R)-3-hydroxyvalerate
≥98.0% (sum of enantiomers, GC)
Synonym(s):
(−)-Methyl (R)-3-hydroxypentanoate
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About This Item
Empirical Formula (Hill Notation):
C6H12O3
CAS Number:
Molecular Weight:
132.16
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4655380
Assay:
≥98.0% (sum of enantiomers, GC)
Quality Level
assay
≥98.0% (sum of enantiomers, GC)
optical activity
[α]20/D −37±3°, c = 1% in chloroform
refractive index
n20/D 1.427
bp
68-70 °C/5 mmHg (lit.)
density
1.029 g/mL at 20 °C (lit.)
functional group
ester, hydroxyl
SMILES string
CC[C@@H](O)CC(=O)OC
InChI
1S/C6H12O3/c1-3-5(7)4-6(8)9-2/h5,7H,3-4H2,1-2H3/t5-/m1/s1
InChI key
XHFXKKFVUDJSPJ-RXMQYKEDSA-N
Application
- Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1-naphthyl)propionic acid.: This research outlines the synthesis of a single-enantiomer pheromone compound using (S)-2-methoxy-2-(1-naphthyl)propionic acid. The process highlights the importance of enantiopure intermediates like (−)-Methyl (R)-3-hydroxyvalerate in the synthesis of biologically active compounds (Ichikawa and Ono, 2006).
Other Notes
Chiral building block for EPC syntheses; selective anti-alkylation of its dianion; OH protection and reduction of ester group to aldehyde or alcohol functions; stereoselective preparation of a dioxanone with pivalaldehyde
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
168.8 °F - closed cup
flash_point_c
76 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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G. Frater
Helvetica Chimica Acta, 62, 2825-2825 (1979)
P. DeShong et al.
Tetrahedron Letters, 27, 2091-2091 (1986)
K. Mori et al.
Tetrahedron, 41, 919-919 (1985)