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Sigma-Aldrich

(−)-Methyl (R)-3-hydroxyvalerate

≥98.0% (sum of enantiomers, GC)

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Synonym(s):
(−)-Methyl (R)-3-hydroxypentanoate
Empirical Formula (Hill Notation):
C6H12O3
CAS Number:
Molecular Weight:
132.16
Beilstein/REAXYS Number:
4655380
MDL number:
PubChem Substance ID:

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.)

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

Related Categories

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_germany

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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