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Sigma-Aldrich

(R)-(−)-Hexahydromandelic acid

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

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Synonym(s):
(R)-(−)-Cyclohexylhydroxyacetic acid
Linear Formula:
C6H11CH(OH)CO2H
CAS Number:
Molecular Weight:
158.19
Beilstein:
3196809
MDL number:
UNSPSC Code:
51113400
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

optical activity

[α]18/D −23°, c = 1 in acetic acid

optical purity

ee: 99% (GLC)

mp

127-129 °C (lit.)

SMILES string

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

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

InChI key

RRDPWAPIJGSANI-SSDOTTSWSA-N

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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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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