Mandelic acid

  • GreenMolBD CID : 4588
  • Molecular Formula : C8H8O3
  • Molecular Weight : 152.149
  • Exact Molecular Mass : 152.047
  • IUPAC Name : 2-hydroxy-2-phenylacetic acid
  • InChI : InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)
  • InChI Key : IWYDHOAUDWTVEP-UHFFFAOYSA-N
  • Canonical SMILES : C1=CC=C(C=C1)C(C(=O)O)O
  • Isomeric SMILES : c1ccc(cc1)C(C(=O)O)O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

1.2. Taxonomy Tree

1.3. Alternative Parent

Alpha hydroxy acids and derivatives; Secondary alcohols; Monocarboxylic acids and derivatives; Carboxylic acids; Organic oxides; Hydrocarbon derivatives; Carbonyl compounds; Aromatic alcohols;

1.4. Molecular Framework

Aromatic homomonocyclic compounds

1.5. Substituents

Hydroxy acid; Monocyclic benzene moiety; Alpha-hydroxy acid; Secondary alcohol; Monocarboxylic acid or derivatives; Carboxylic acid; Carboxylic acid derivative; Organic oxygen compound; Organic oxide; Hydrocarbon derivative; Aromatic alcohol; Organooxygen compound; Carbonyl group; Alcohol; Aromatic homomonocyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
0.9001 57.53 2 3 11 2 6 6 3.91486 195.952 158.439 0.776462

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-117.141853 2.52 -5.063 -9.95491 -0.17011 4.892

4. Compound Reactivity

DLP nRFG nLMR
0 0 2

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Non-Mutagen Non-Toxic 2.09256 2700.79 0.293203 None None Moderate Degradable 0.474011 101.587

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes No Yes Yes Yes Yes

7. Synonyms

Name
MANDELIC ACID
dl-Mandelic acid
2-hydroxy-2-phenylacetic acid
90-64-2
Amygdalic acid
Phenylglycolic acid
Almond acid
611-72-3
Uromaline
p-Mandelic acid
Racemic mandelic acid
Paramandelic acid
(RS)-Mandelic acid
2-Phenylglycolic acid
Hydroxy(phenyl)acetic acid
Phenylhydroxyacetic acid
Glycolic acid, phenyl-
alpha-Hydroxyphenylacetic acid
Acido mandelico
(+-)-Mandelic acid
Amygdalinic acid
Kyselina mandlova
2-Phenyl-2-hydroxyacetic acid
alpha-Hydroxy-alpha-toluic acid
2-Hydroy-2-phenylacetic acid
DL-Hydroxy(phenyl)acetic acid
Mandelic acid [USP]
Benzeneacetic acid, .alpha.-hydroxy-
Acido mandelico [Italian]
alpha-Toluic acid, alpha-hydroxy-
Kyselina mandlova [Czech]
NSC 7925
(+-)-alpha-Hydroxybenzeneacetic acid
(+/-)-alpha-Hydroxyphenylacetic acid
alpha-Hydroxybenzeneacetic acid
(+-)-2-Hydroxy-2-phenylethanoic acid
2-hydroxy-2-phenyl-acetic acid
(+/-)-mandelic acid
DL-2-Hydroxy-2-phenylacetic acid
Kyselina 2-fenyl-2-hydroxyethanova
(+-)-alpha-Hydroxyphenylacetic acid
EINECS 202-007-6
EINECS 210-277-1
alpha-Hydroxybenzeneacetic acid, (+-)-
AI3-06293
Kyselina 2-fenyl-2-hydroxyethanova [Czech]
.alpha.-Hydroxyphenylacetic acid
CHEBI:35825
Phenylacetic acid, alpha-hydroxy-
IWYDHOAUDWTVEP-UHFFFAOYSA-N
Benzeneacetic acid, alpha-hydroxy-
.alpha.-Hydroxy-.alpha.-toluic acid
.alpha.-Toluic acid, .alpha.-hydroxy-
(+)-Mandelate, XXI
Benzeneacetic acid, .alpha.-hydroxy-, (.+/-.)-
DL-Amygdalic Acid
(R)-Hydroxyphenylaceticacid
2-Hydroxy-2-phenylethanoic acid
acidomandelico
amigdalinicacid
mandelic-acid
DL-Mandelicacid
Benzoglycolic acid
NCGC00166022-01
()-Mandelic acid
l(+)mandelic acid
R,S-Mandelic Acid
(+) mandelic acid
(+)-mandelic acid
PPCM
SAMMA
hyroxyphenylacetic acid
(+/-)-alpha-Hydroxybenzeneacetic acid
Mandelic acid, 99%
(-)-Mandelate, XX
hydroxyphenyl acetic acid
WLN: QYR&VQ
hydroxy-phenyl-acetic acid
Mandelic acid, >=99%
DL-Mandelic acid, 99%
AC1L1B5K
SCHEMBL1050
(.+/-.)-Mandelic acid
CHEMBL1609
alpha-hydroxy-alpha-toluicaci
(+)-Phenylhydroxyacetic acid
(?)-Phenylhydroxyacetic acid
alpha-hydroxy-benzeneaceticaci
alpha-Phenylhydroxyacetic acid
KSC498C0D
MLS001074208
ARONIS25152
Jsp003513
.alpha.-Phenylhydroxyacetic acid
DTXSID6023234
BDBM92715
Benzeneacetic acid, |A-hydroxy-
CTK3J8101
NSC7925
Mandelic acid condensation polymer
MolPort-000-144-484
2-oxidanyl-2-phenyl-ethanoic acid
BB_NC-2227
HMS2230F19
HMS3371M20
HMS3373A03
(2rs)-hydroxy(phenyl)ethanoic acid
NSC-7925
530-31-4 (mono-ammonium salt)
ANW-43754
BBL028097
MFCD00064250
SBB007730
STL283951
AKOS000118795
AKOS016050628
114-21-6 (mono-hydrochloride salt)
ALPHA-HYDROXY-BENZENEACETIC ACID
EBD2224148
KS-1423
LS00073
MCULE-3206518139
MP-2164
QC-1264
RP21581
RTR-021071
134-95-2 (calcium[2:1] salt)
Benzeneacetic acid, ?-hydroxy-, (S)-
KS-0000472D
(+/-)-Mandelic acid, 99% 100g
NCGC00166023-01
NCGC00166269-01
(.+/-.)-alpha-Hydroxybenzeneacetic acid
AC-12228
AK-54084
AN-13931
AN-21623
AN-24198
BC204233
BC250758
BR-54084
BT000169
KB-03390
LS-89042
OR012034
SC-45533
SMR000653543
AB1004330
KB-173030
RT-000957
TR-021071
AM20060842
FT-0083191
FT-0625487
FT-0628148
ST24022254
W7345
Benzeneacetic acid, .alpha.-hydroxy-, ( )-
Benzeneacetic acid, .alpha.-hydroxy-, (S)-
A19434
DL-Mandelic acid, analytical reference material
MLS-0090887.0001
11048-EP2269610A2
11048-EP2269986A1
11048-EP2269988A2
11048-EP2270006A1
11048-EP2270008A1
11048-EP2270011A1
11048-EP2270014A1
11048-EP2275401A1
11048-EP2275413A1
11048-EP2277848A1
11048-EP2277858A1
11048-EP2277867A2
11048-EP2280003A2
11048-EP2281563A1
11048-EP2284160A1
11048-EP2284178A2
11048-EP2284179A2
11048-EP2287156A1
11048-EP2289510A1
11048-EP2289518A1
11048-EP2289890A1
11048-EP2292231A1
11048-EP2292617A1
11048-EP2295433A2
11048-EP2298735A1
11048-EP2298746A1
11048-EP2298747A1
11048-EP2298755A1
11048-EP2298758A1
11048-EP2298759A1
11048-EP2298767A1
11048-EP2298779A1
11048-EP2301931A1
11048-EP2301937A1
11048-EP2305257A1
11048-EP2305641A1
11048-EP2305646A1
11048-EP2305651A1
11048-EP2305664A1
11048-EP2305672A1
11048-EP2305675A1
11048-EP2308849A1
11048-EP2308850A1
11048-EP2308851A1
11048-EP2308854A1
11048-EP2308857A1
11048-EP2308869A1
11048-EP2311807A1
11048-EP2311809A1
11048-EP2311810A1
11048-EP2311842A2
11048-EP2314587A1
11048-EP2314593A1
11048-EP2316457A1
11048-EP2316458A1
11048-EP2316459A1
11048-EP2316825A1
11048-EP2316826A1
11048-EP2316827A1
11048-EP2316828A1
Benzeneaceticacid
A833072
AE-562/40233036
Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.R)-
Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.S)-
I01-1029
I01-4449
I14-0792
(2RS)-2-Hydroxy-2-phenylacetic Acid (Mandelic Acid)
Mandelic Acid ((2RS)-2-Hydroxy-2-phenylacetic Acid)
14A53E4A-8315-42A7-9D60-DE06CCBB1AF9
F2191-0202
Z955123532
Mandelic acid, United States Pharmacopeia (USP) Reference Standard
15769-78-5
71036-61-8
CS-W016307
BG00600678

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Mandelic acid
Echinochloa cruss-galli Root 3

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
197 DNA polymerase kappa POLK Homo sapiens 26.6795 588579
197 DNA polymerase kappa POLK Homo sapiens 29.9349 588579
970 dual specificity phosphatase 6 Dusp6 Rattus norvegicus 100 1052
970 dual specificity phosphatase 6 Dusp6 Rattus norvegicus 100 1054
970 dual specificity phosphatase 6 Dusp6 Rattus norvegicus 100 1055
440 glyceraldehyde-3-phosphate dehydrogenase GAPDH Homo sapiens 100 1227
983 heat shock protein family A (Hsp70) member 8 HSPA8 Homo sapiens 100 1193
28 lamin A/C LMNA Homo sapiens 7.9433 1487
446 Procollagen-proline,2-oxoglutarate-4-dioxygenase Gallus gallus >20000000 3011801
206 protein tyrosine phosphatase, non-receptor type 7 PTPN7 Homo sapiens 100 1059
206 protein tyrosine phosphatase, non-receptor type 7 PTPN7 Homo sapiens 100 1077
184 thioredoxin reductase 1 Txnrd1 Rattus norvegicus 79.4328 588453

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
277292052MolCoreSource URLSource DetailCS15279Source Record URL
318242845Yuhao ChemicalSource URLSource DetailJZ1417Source Record URL
347729669Yuhao ChemicalSource URLSource DetailLX2232Source Record URL
318240168Yuhao ChemicalSource URLSource DetailXJ0179Source Record URL
346564089LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00174005Source Record URL
87572154TCI (Tokyo Chemical Industry)Source URLSource DetailM0038Source Record URL
252256430Wilshire TechnologiesSource URLSource DetailMandelic AcidSource Record URL
292611775Aurora Fine Chemicals LLCSource URLSource DetailA00.003.082Source Record URL
276935133Aurora Fine Chemicals LLCSource URLSource DetailK04.633.125Source Record URL
254781193Boc SciencesSource URLSource Detail611-72-3Source Record URL
275877112BePharm Ltd.Source URLSource DetailB21766Source Record URL
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329817945Sigma-AldrichSource URLSource DetailM2625_SIGMASource Record URL
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346520761King ScientificSource URLSource DetailKS-0000472DSource Record URL
163812733King ScientificSource URLSource DetailKSC498C0DSource Record URL
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