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Merck
CN

301140

(R)-(−)-Hexahydromandelic acid

98%, optical purity ee: 99% (GLC)

Synonym(s):

(R)-(−)-Cyclohexylhydroxyacetic acid

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About This Item

Linear Formula:
C6H11CH(OH)CO2H
CAS Number:
Molecular Weight:
158.19
UNSPSC Code:
51113400
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3196809
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Product Name

(R)-(−)-Hexahydromandelic acid, 98%, optical purity ee: 99% (GLC)

InChI

1S/C8H14O3/c9-7(8(10)11)6-4-2-1-3-5-6/h6-7,9H,1-5H2,(H,10,11)/t7-/m1/s1

SMILES string

O[C@H](C1CCCCC1)C(O)=O

InChI key

RRDPWAPIJGSANI-SSDOTTSWSA-N

assay

98%

optical activity

[α]18/D −23°, c = 1 in acetic acid

optical purity

ee: 99% (GLC)

mp

127-129 °C (lit.)

functional group

carboxylic acid
hydroxyl

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Application

(R)-(−)-Hexahydromandelic acid can be used:
  • As an intermediate in the synthesis of antimycobacterial compound pyridomycin analogs.
  • As a model α-hydroxy acid compound in the chirality sensing studies of organic probes using circular dichroism technique.
  • As a starting material in the synthesis of chiral ionic liquids, which are applicable as chiral solvents in asymmetric synthesis and as chiral stationary phases in chromatographic separations.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Chiral ionic liquids: synthesis, properties, and enantiomeric recognition
Yu S, et al.
The Journal of Organic Chemistry, 73(7), 2576-2591 (2008)
Synthesis and Structure-Activity Relationship Studies of C2-Modified Analogs of the Antimycobacterial Natural Product Pyridomycin
Kienle M, et al.
Journal of medicinal chemistry, 63(3), 1105-1131 (2020)
Chirality sensing of amines, diamines, amino acids, amino alcohols, and ?-hydroxy acids with a single probe
Bentley KW, et al.
Journal of the American Chemical Society, 135(48), 18052-18055 (2013)

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