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Merck
CN

M2500

Sigma-Aldrich

D-(−)-Mandelic acid

Sigma Grade

Synonym(s):

(R)-α-Hydroxyphenylacetic acid

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About This Item

Empirical Formula (Hill Notation):
C8H8O3
CAS Number:
611-71-2
Molecular Weight:
152.15
Beilstein:
2691094
EC Number:
210-276-6
MDL number:
MFCD00064251
UNSPSC Code:
12352103

Key Documents

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grade

Sigma Grade

optical activity

[α]20/D ~−155°, c = 2.3 in H2O(lit.)

mp

~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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Other Notes

The nomenclature of mandelic acid isomers has been confused. This isomer was formerly named L(—)mandelic acid.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Flash Point(F)

>374.0 °F

Flash Point(C)

> 190 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
083H2501
038F0416
081K2618

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Jennifer R Bourque et al.
Bioorganic & medicinal chemistry letters, 17(1), 105-108 (2006-10-24)
Mandelate racemase (MR) catalyzes the 1,1-proton transfer that interconverts the enantiomers of mandelate. The transition state/intermediate analogues N-hydroxyformanilide (K(i)=2.79+/-0.19 microM) and cupferron (K(i)=2.67+/-0.09 microM) are identified as potent competitive inhibitors of MR. The pH-pK(i) profile indicates that MR can bind

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