All Photos(1)
Synonym(s):
(R)-α-Hydroxyphenylacetic acid
Linear Formula:
C6H5CH(OH)CO2H
CAS Number:
Molecular Weight:
152.15
Beilstein:
2691094
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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
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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.
(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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1
WGK
WGK 1
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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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)
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
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)
Chromatograms
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