ChemFOnt: Showing chemical card for p-Hydroxymandelic acid (CFc000000657)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:06 UTC

Chemfont ID

CFc000000657

Molecule Identification

Common Name

p-Hydroxymandelic acid

Definition

p-Hydroxymandelic acid is an acidic metabolite of p-octopamine and p-synephrine (p-phenylephrine). It is also a naturally occurring metabolite of tyramine. A specific enantiomer of p-hydroxymandelic aicd ((R)-(-)-p-hydroxymandelic -- also called pisolithin B) has been shown to exhibit antifungal properties.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxyphenylglycolic acid	ChEBI
4-Hydroxyphenylglycolate	Generator
4-Hydroxymandelate	Generator
p-Hydroxymandelate	Generator
(+/-)-alpha,4-dihydroxy-benzeneacetate	HMDB
(+/-)-alpha,4-dihydroxy-benzeneacetic acid	HMDB
(R)-4-Hydroxymandelate	HMDB
(RS)-p-Hydroxymandelate	HMDB
(RS)-p-Hydroxymandelic acid	HMDB
(S)-4-Hydroxymandelate	HMDB
2-(4-Hydroxyphenyl)-2-hydroxyacetate	HMDB
2-(4-Hydroxyphenyl)-2-hydroxyacetic acid	HMDB
3-Dimethylallyl-4-hydroxymandelate	HMDB
3-Dimethylallyl-4-hydroxymandelic acid	HMDB
4-Hydroxy-DL-mandelate	HMDB
4-Hydroxy-DL-mandelic acid	HMDB
alpha,4-Dihydroxy-benzeneacetate	HMDB
alpha,4-Dihydroxy-benzeneacetic acid	HMDB
alpha,4-Dihydroxybenzeneacetate	HMDB
alpha,4-Dihydroxybenzeneacetic acid	HMDB
D-4-Hydroxymandelate	HMDB
D-p-Hydroxymandelate	HMDB
delta-4-Hydroxymandelate	HMDB
delta-p-Hydroxymandelate	HMDB
DL-4-Hydroxymandelate	HMDB
DL-4-Hydroxymandelic acid	HMDB
DL-p-Hydroxymandelate	HMDB
DL-p-Hydroxymandelic acid	HMDB
DL-p-Hydroxyphenylglycolate	HMDB
DL-p-Hydroxyphenylglycolic acid	HMDB
Hydroxy(4-hydroxyphenyl)acetate	HMDB
Hydroxy(4-hydroxyphenyl)acetic acid	HMDB
L-4-Hydroxymandelate	HMDB
L-p-Hydroxymandelate	HMDB
p-Hydroxy-mandelate	HMDB
p-Hydroxy-mandelic acid	HMDB
p-Hydroxyphenylglycolate	HMDB
p-Hydroxyphenylglycolic acid	HMDB
Para-hydroxymandelic acid	HMDB
4-Hydroxymandelic acid, (D)-isomer	HMDB
Pisolithin b	HMDB
2-Hydroxy-2-(4'-hydroxyphenyl)acetic acid	HMDB
2-Hydroxy-2-(4-hydroxyphenyl)acetic acid	HMDB

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

IUPAC Name

2-hydroxy-2-(4-hydroxyphenyl)acetic acid

Traditional Name

4-hydroxymandelic acid

CAS Registry Number

1198-84-1

SMILES

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

InChI Identifier

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

InChI Key

YHXHKYRQLYQUIH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

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:16388 )
2-hydroxy carboxylic acid (CHEBI:16388 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000822)
Vitreous humor (HMDB: HMDB0000822)

Cellular substructure

Membrane (HMDB: HMDB0000822)
Cell membrane (HMDB: HMDB0000822)

Organ substructure

Retina (HMDB: HMDB0000822)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 25037050)

Source

Endogenous

Endogenous (HMDB: HMDB0000822)

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)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.69 g/L	ALOGPS
logP	0.86	ALOGPS
logP	0.59	ChemAxon
logS	-1.3	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	15.64 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

HMDB0000822

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022267

KNApSAcK ID

Not Available

Chemspider ID

321

KEGG Compound ID

C11527

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Hydroxymandelic acid

METLIN ID

5785

PubChem Compound

328

PDB ID

Not Available

ChEBI ID

16388

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Wang, Bing; Zhang, Guofeng. Synthesis and purity determination of p-hydroxymandelic acid. Qingdao Daxue Xuebao, Gongcheng Jishuban (1999), 14(1), 14-16.

Showing chemical card for p-Hydroxymandelic acid (CFc000000657)

MOL for CFc000000657 (p-Hydroxymandelic acid)

3D MOL for CFc000000657 (p-Hydroxymandelic acid)

3D SDF for CFc000000657 (p-Hydroxymandelic acid)

3D-SDF for CFc000000657 (p-Hydroxymandelic acid)

PDB for CFc000000657 (p-Hydroxymandelic acid)

3D PDB for CFc000000657 (p-Hydroxymandelic acid)

SMILES for CFc000000657 (p-Hydroxymandelic acid)

INCHI for CFc000000657 (p-Hydroxymandelic acid)

Structure for CFc000000657 (p-Hydroxymandelic acid)

3D Structure for CFc000000657 (p-Hydroxymandelic acid)