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154210 Sigma-Aldrich

(R)-(−)-Mandelic acid

ReagentPlus®, ≥99%

Synonym: (R)-α-Hydroxyphenylacetic acid

  • CAS Number 611-71-2

  • Linear Formula C6H5CH(OH)CO2H

  • Molecular Weight 152.15

  •  Beilstein/REAXYS Number 2691094

  •  EC Number 210-276-6

  •  MDL number MFCD00064251

  •  PubChem Substance ID 24849414

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Carboxylic Acids, Chemical Synthesis, Chiral Building Blocks, Chiral Resolution Reagents,
Quality Level   100
product line   ReagentPlus®
assay   ≥99%
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

Description

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.

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.

Packaging

25 g in poly bottle

5 g in glass bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
Flash Point(F) 
374.0 °F
Flash Point(C) 
> 190 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

GC Analysis of Mandelic Acid Methyl Ester Enantiomers on Astec® CHIRALDEX® B-DP

From our library of Articles, Sigma-Aldrich presents GC Analysis of Mandelic Acid Methyl Ester Enantiomers on Astec® CHIRALDEX® B-DP
Keywords: Chromatography, Flame ionization detector, Gas chromatography, Purification

GC Analysis of Mandelic Acid Methyl Ester Enantiomers on Astec® CHIRALDEX® G-TA

From our library of Articles, Sigma-Aldrich presents GC Analysis of Mandelic Acid Methyl Ester Enantiomers on Astec® CHIRALDEX® G-TA
Keywords: Chromatography, Flame ionization detector, Gas chromatography, Purification

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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