MilliporeSigma
All Photos(1)

Documents

154210

Sigma-Aldrich

(R)-(−)-Mandelic acid

ReagentPlus®, ≥99%

Sign Into View Organizational & Contract Pricing

Synonym(s):
(R)-α-Hydroxyphenylacetic acid
Linear Formula:
C6H5CH(OH)CO2H
CAS Number:
Molecular Weight:
152.15
Beilstein/REAXYS Number:
2691094
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
M2209336505727075
(R)-(−)-Mandelic acid ReagentPlus®, ≥99%

154210

(R)-(−)-Mandelic acid

(R)-(−)-Mandelic acid 98%

M2209

(R)-(−)-Mandelic acid

(R)-(−)-1-Cyclohexylethylamine 98%

336505

(R)-(−)-1-Cyclohexylethylamine

(R)-(−)-Mandelic acid ChiPros®, produced by BASF, 99%

727075

(R)-(−)-Mandelic acid

Quality Level

100

Quality Level

-

Quality Level

-

Quality Level

-

form

solid

form

-

form

liquid

form

crystals

mp

131-133 °C (lit.)

mp

131-133 °C (lit.)

mp

-

mp

131-133 °C (lit.)

product line

ReagentPlus®

product line

-

product line

-

product line

-

optical activity

[α]23/D −153°, c = 2.5 in H2O

optical activity

[α]25/D −151°, c = 1 in ethanol

optical activity

[α]20/D −4°, neat, [α]20/D -3.8±0.3°, neat

optical activity

-

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

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

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)
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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service