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Safety Information

154210

Sigma-Aldrich

(R)-(−)-Mandelic acid

ReagentPlus®, ≥99%

Synonym(s):

(R)-α-Hydroxyphenylacetic acid

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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

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, is also used as a building block to synthesize pharmaceutical drugs such as penicillin and cephalosporin. It can be synthesized from (R,S)-mandelonitrile with high yield and enantioselectivity using nitrilase enzyme .

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

Application

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

154210-5G:
154210-BULK:
154210-10KG:
154210-5KG:
154210-25G:
154210-500G:
154210-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK0343
STBH9772
STBG9274
STBF2729V
STBF1844V

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Enzyme-catalysed optical resolution of mandelic acid via RS (?)-methyl mandelate in non-aqueous media.
Yadav GD and Sivakumar P.
Biochemical Engineering Journal, 19(2), 101-107 (2004)
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)
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)
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)
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