ChemFOnt: Showing chemical card for 3-Hydroxymandelic acid (CFc000000598)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:01 UTC

Chemfont ID

CFc000000598

Molecule Identification

Common Name

3-Hydroxymandelic acid

Definition

3-Hydroxymandelic acid, also known as m-hydroxymandelate or MHMA, is a 2-hydroxy monocarboxylic acid. 3-Hydroxymandelic acid is the dehydroxylated (positions 2 and 3‚Äô) derivative of phenylacetic acid. It is a white crystalline solid that is soluble in water and polar organic solvents. It derives from a mandelic acid. Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway. Mandelate racemase interconverts the two enantiomers via a pathway that involves cleavage of the alpha-CH bond. Mandelate dehydrogenase is yet another enzyme on this pathway. Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated. Derivatives of mandelic acid, such as 3-hydroxymandelic acid, are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxy-2-(3-hydroxyphenyl)acetic acid	ChEBI
m-Hydroxymandelic acid	ChEBI
2-Hydroxy-2-(3-hydroxyphenyl)acetate	Generator
2-Hydroxy-2-(3-hydroxyphenyl)ethanoate	Generator
m-Hydroxymandelate	Generator
3-Hydroxymandelate	Generator
3-Hydroxyphenylglycolic acid	HMDB
alpha,3-Dihydroxybenzeneacetic acid	HMDB
DL-3-Hydroxymandelate	HMDB
DL-3-Hydroxymandelic acid	HMDB
DL-Hydroxy(m-hydroxyphenyl)acetic acid	HMDB
Hydroxy(3-hydroxyphenyl)acetic acid	HMDB
m-Hydroxy-(6ci,7ci,8ci)mandelate	HMDB
m-Hydroxy-(6ci,7ci,8ci)mandelic acid	HMDB
Meta-hydroxymandelic acid	HMDB
MHMA	HMDB
2-Hydroxy-2-(3'-hydroxyphenyl)acetic acid	HMDB

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

IUPAC Name

2-hydroxy-2-(3-hydroxyphenyl)acetic acid

Traditional Name

MHMA

CAS Registry Number

17119-15-2

SMILES

OC(C(O)=O)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)

InChI Key

OLSDAJRAVOVKLG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alpha-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Aromatic alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:86553 )
2-hydroxy monocarboxylic acid (CHEBI:86553 )

Functional Ontology

Physiological effect

Health effect

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0000750)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000750)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000750)
Feces (PMID: 24010549)

Organ

Liver (HMDB: HMDB0000750)
Kidney (HMDB: HMDB0000750)

Cellular substructure

Cytoplasm (HMDB: HMDB0000750)

Source

Endogenous

Endogenous (HMDB: HMDB0000750)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	10.5 g/L	ALOGPS
logP	0.89	ALOGPS
logP	0.59	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.68 m³·mol⁻¹	ChemAxon
Polarizability	15.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000750

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022222

KNApSAcK ID

Not Available

Chemspider ID

78444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Hydroxymandelic acid

METLIN ID

732

PubChem Compound

86957

PDB ID

Not Available

ChEBI ID

86553

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Fanali S; Aturki Z Further study on the use of uncharged beta-cyclodextrin polymer in capillary electrophoresis: enantiomeric separation of some alpha-hydroxy acids. Electrophoresis (1995), 16(8), 1505-9.

Showing chemical card for 3-Hydroxymandelic acid (CFc000000598)

MOL for CFc000000598 (3-Hydroxymandelic acid)

3D MOL for CFc000000598 (3-Hydroxymandelic acid)

3D SDF for CFc000000598 (3-Hydroxymandelic acid)

3D-SDF for CFc000000598 (3-Hydroxymandelic acid)

PDB for CFc000000598 (3-Hydroxymandelic acid)

3D PDB for CFc000000598 (3-Hydroxymandelic acid)

SMILES for CFc000000598 (3-Hydroxymandelic acid)

INCHI for CFc000000598 (3-Hydroxymandelic acid)

Structure for CFc000000598 (3-Hydroxymandelic acid)

3D Structure for CFc000000598 (3-Hydroxymandelic acid)