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154210

Sigma-Aldrich

(R)-(−)-Mandelic acid

ReagentPlus®, ≥99%

Synonym(s):

(R)-α-Hydroxyphenylacetic acid

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5 G
MXP 854.00
25 G
MXP 2,351.00

MXP 854.00

Estimated to ship onApril 07, 2025

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5 G
MXP 854.00
25 G
MXP 2,351.00

About This Item

Linear Formula:
C6H5CH(OH)CO2H
CAS Number:
611-71-2
Molecular Weight:
152.15
Beilstein:
2691094
EC Number:
210-276-6
MDL number:
MFCD00064251
UNSPSC Code:
12352106
PubChem Substance ID:
24849414
NACRES:
NA.22

MXP 854.00

Estimated to ship onApril 07, 2025

Request a Bulk Order

Quality Level

100

product line

ReagentPlus®

Assay

≥99%

form

solid

optical activity

[α]23/D −153°, c = 2.5 in H2O

mp

131-133 °C (lit.)

SMILES string

O[C@@H](C(O)=O)c1ccccc1

InChI

1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1

InChI key

IWYDHOAUDWTVEP-SSDOTTSWSA-N

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General description

(R)-(-)-Mandelic acid, a chiral resolving agent,[1] is also used as a building block to synthesize pharmaceutical drugs such as penicillin and cephalosporin.[2] It can be synthesized from (R,S)-mandelonitrile with high yield and enantioselectivity using nitrilase enzyme[3] [1] [2].

(R)-(−)-Mandelic acid is a carboxylic acid used as a starting material to synthesize antibiotics, antitumor agents, and antiobesity drugs. [4]

Application

(R)-(-)-Mandelic acid has been used in studies to assess its ability to undergo spontaneous oscillatory chiral conversion[5] and spontaneous condensation to form polymandelic acid.[6]

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK0343
STBH9772
STBG9274
STBF2729V
STBF1844V

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Green synthesis aspects of (R)-(-)-mandelic acid; a potent pharmaceutically active agent and its future prospects
Rahul Vikram S et al.
Critical Reviews in Biotechnology, 43, 1226-1235 (2023)
Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750.
Yamamoto K, et al.
Applied and Environmental Microbiology, 57(10), 3028-3032 (1991)
On the spontaneous condensation of selected hydroxy acids.
Sajewicz M, et al.
Acta Chromatographica , 21(2), 259-271 (2009)
TLC in a search for structural limitations of spontaneous oscillatory in-vitro chiral conversion. a-hydroxybutyric and mandelic acids.
Sajewicz M, et al.
J. Planar Chromatogr., 22(4), 241-248 (2009)
Ya-Ping Xue et al.
Journal of industrial microbiology & biotechnology, 38(2), 337-345 (2010-07-20)
(R)-(-)-Mandelic acid (R-MA) is an important intermediate with broad uses. Recently, R-MA production using nitrilase has been gaining more and more attention due to its higher productivity and enantioselectivity. In this work, a new bacterium WT10, which exhibited favorable nitrilase
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