M2500
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:
Molecular Weight:
152.15
EC Number:
210-276-6
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
2691094
InChI key
IWYDHOAUDWTVEP-SSDOTTSWSA-N
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
SMILES string
O[C@@H](C(O)=O)c1ccccc1
grade
Sigma Grade
optical activity
[α]20/D ~−155°, c = 2.3 in H2O(lit.)
mp
~133 °C (lit.)
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Other Notes
The nomenclature of mandelic acid isomers has been confused. This isomer was formerly named L(—)mandelic acid.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1
Storage Class
13 - Non Combustible Solids
wgk
WGK 1
flash_point_f
>374.0 °F
flash_point_c
> 190 °C
ppe
Eyeshields, Gloves, type N95 (US)
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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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