Showing Compound 4-Hydroxyphenylacetic acid (FDB010534)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:10 UTC

Update date

2024-11-29 22:27:57 UTC

Primary ID

FDB010534

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Hydroxyphenylacetic acid

Description

p-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate or parahydroxy phenylacetate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). p-Hydroxyphenylacetic acid exists in all living species, ranging from bacteria to humans. p-Hydroxyphenylacetic acid is found, on average, in the highest concentration within a few different foods, such as olives, american cranberries, and grape wines and in a lower concentration in corns, beers, and oats. p-Hydroxyphenylacetic acid has also been detected, but not quantified in, several different foods, such as dandelions, common wheats, cocoa beans, milk (cow), and evening primroses. This could make p-hydroxyphenylacetic acid a potential biomarker for the consumption of these foods. p-Hydroxyphenylacetic acid is a potentially toxic compound. p-Hydroxyphenylacetic acid, with regard to humans, has been found to be associated with several diseases such as schizophrenia, crohn's disease, spina bifida, and ulcerative colitis; p-hydroxyphenylacetic acid has also been linked to the inborn metabolic disorder phenylketonuria.

CAS Number

156-38-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(p-Hydroxyphenyl)acetic acid	ChEBI
4-Carboxymethylphenol	ChEBI
4-Hydroxybenzeneacetic acid	ChEBI
4-Hydroxyphenylacetate	ChEBI
4-Hydroxyphenylacetic acid	Kegg
(p-Hydroxyphenyl)acetate	Generator
4-Hydroxybenzeneacetate	Generator
p-Hydroxyphenylacetate	Generator
(4-Hydroxy-phenyl)-acetate	HMDB
(4-Hydroxy-phenyl)-acetic acid	HMDB
(4-Hydroxy-phenyl)-essigsaeure	HMDB
(4-Hydroxyphenyl)acetate	HMDB
(4-Hydroxyphenyl)acetic acid	HMDB
(p-Hydroxyphenyl)-acetate	HMDB
(p-Hydroxyphenyl)-acetic acid	HMDB
4-Hydroxy-benzeneacetate	HMDB
4-Hydroxy-benzeneacetic acid	HMDB
4-Hydroxyphenyl-acetic acid	HMDB
Parahydroxy phenylacetate	HMDB
Parahydroxy phenylacetic acid	HMDB
Parahydroxyphenylacetate	HMDB
Para-hydroxyphenylacetic acid	HMDB
p-Hydroxyphenylacetic acid	ChEBI
4'-Hydroxyphenylacetic acid	HMDB
2-(4-Hydroxyphenyl)acetic acid	HMDB
(4-hydroxy-phenyl)-acetate	biospider
(4-hydroxy-phenyl)-acetic acid	biospider
(4-hydroxyphenyl)acetate	biospider
(4-hydroxyphenyl)acetic acid	biospider
(p-hydroxyphenyl)-acetate	biospider
(p-hydroxyphenyl)-acetic acid	biospider
(p-hydroxyphenyl)acetate	biospider
(p-hydroxyphenyl)acetic acid	biospider
3pcg	biospider
4-HPA	biospider
4-Hydroxy-Benzeneacetate	biospider
4-Hydroxy-Benzeneacetic acid	biospider
4-Hydroxybenzeneacetic acid, 9CI	db_source
4-hydroxyphenyl acetate	biospider
4-hydroxyphenylacetate	biospider
Acetic acid, (p-hydroxyphenyl)-	biospider
Benzeneacetic acid, 4-hydroxy-	biospider
DL-para-hydroxyphenylacetic acid	biospider
p-Hydroxy-a-toluic acid	db_source
P-hydroxyphenyl acetic acid	biospider
P-hydroxyphenylacetate	biospider
P-hydroxyphenylacetic acid	biospider

Predicted Properties

Property	Value	Source
Water Solubility	7.12 g/L	ALOGPS
logP	0.93	ALOGPS
logP	1.31	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39.35 m³·mol⁻¹	ChemAxon
Polarizability	14.83 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H8O3

IUPAC name

2-(4-hydroxyphenyl)acetic acid

InChI Identifier

InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)

InChI Key

XQXPVVBIMDBYFF-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CC1=CC=C(O)C=C1

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

Classification

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
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:18101 )
phenols (CHEBI:18101 )

Ontology

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Microbe:

Pseudomonas:

Pseudomonas aeruginosa

Klebsiella:

Klebsiella pneumoniae

Acinetobacter:

Acinetobacter baumannii

Clostridium:

Plant:

Biological location:

Tissue and substructures:

Epidermis

Organ and components:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 63.15%; H 5.30%; O 31.55%	DFC
Melting Point	Mp 148-150°	DFC
Boiling Point	Not Available
Experimental Water Solubility	60.7 mg/mL at 25 oC	GRACIN,S & RASMUSON,AC (2002)
Experimental logP	0.75	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 4.59 (10% EtOH aq.)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1	2014-09-20	View Spectrum
GC-MS	4-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrum	splash10-01ta-1930000000-57c9e8ddaa10569055aa	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrum	splash10-0h01-0940000000-a14203384331e709252f	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-03fs-1930000000-80c21819072fb01958dc	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrum	splash10-00di-9410000000-678591f03aba45c2a6ae	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrum	splash10-0h0r-2940000000-760b6c506072a61059c0	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-2900000000-3939c62b0d7f649ff402	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-6900000000-fdb73325a31c758496e9	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0gyk-0980000000-ed36f36969e4d51b9a8d	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-01ta-1930000000-57c9e8ddaa10569055aa	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0h01-0940000000-a14203384331e709252f	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-03fs-1930000000-80c21819072fb01958dc	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-00di-9410000000-678591f03aba45c2a6ae	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0h0r-2940000000-760b6c506072a61059c0	Spectrum
GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-03fs-1931100000-50456fed0c5ef95ecb57	Spectrum
Predicted GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-4900000000-b6f6363476ffa290862f	Spectrum
Predicted GC-MS	4-Hydroxyphenylacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-5930000000-abf5245dd22d012d04f8	Spectrum
Predicted GC-MS	4-Hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxyphenylacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxyphenylacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxyphenylacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxyphenylacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxyphenylacetic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0pb9-0900000000-e3dfb4b180d858b3a854	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-056r-9400000000-9a6cb39e019a0b40a666	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0kdl-9400000000-35ecc22161defddc7b21	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-0a4i-2900000000-3939c62b0d7f649ff402	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0a4i-6900000000-fdb73325a31c758496e9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-4900000000-88da569804a98e1a99ea	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9300000000-eef23e2f30d876f4a1f9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-0a95379b7cea57386b0b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-4900000000-88da569804a98e1a99ea	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9300000000-eef23e2f30d876f4a1f9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-0a95379b7cea57386b0b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0900000000-02cd23fa5ff37594d2be	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0900000000-bbac468eb7ce6ea99123	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-1900000000-05d18e7bb4163e35e2aa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-1900000000-9a0086561d6f8a169670	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-398dff08b5b2a56e658c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-5f75ea6de2d6bad624d8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9700000000-68d0f4a3b2f7ccfcc2a4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-7ce02fea5a9ef38024f2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-0900000000-12e388b0927ed1c6e166	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-2900000000-ae1870eee4853c57a447	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18101

Phenol-Explorer ID

573

DrugBank ID

Not Available

HMDB ID

HMDB00020

CRC / DFC (Dictionary of Food Compounds) ID

FCL13-X:FCL13-X

EAFUS ID

Not Available

Dr. Duke ID

4-HYDROXYPHENYLACETIC-ACID|P-HYDROXYPHENYLACETIC-ACID

BIGG ID

35599

KNApSAcK ID

Not Available

HET ID

4HP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

573

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Tyrosine Metabolism	SMP00006	map00350
Metabolism and Physiological Effects of Para-cresol	SMP0123214	Not Available
Metabolism and Physiological Effects of Para-cresyl glucuronide	SMP0123299	Not Available
Metabolsim and Physiological Effects of 4-Ethylphenylsulfate	SMP0125541	Not Available
Metabolism and Physiological Effects of p-Cresol sulphate	SMP0126850	Not Available
Metabolism and Physiological Effects of 4-Hydroxyphenylacetic acid	SMP0126879	Not Available