Showing Compound 3-Hydroxyphenylacetic acid (FDB022047)

Record Information

Version

1.0

Creation date

2011-09-21 00:07:32 UTC

Update date

2019-11-26 03:21:01 UTC

Primary ID

FDB022047

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Hydroxyphenylacetic acid

Description

3-Hydroxyphenylacetic acid, also known as (m-hydroxyphenyl)acetate or 3-hydroxybenzeneacetate, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. 3-Hydroxyphenylacetic acid exists in all living organisms, ranging from bacteria to humans. 3-Hydroxyphenylacetic acid has been detected, but not quantified in, milk (cow). This could make 3-hydroxyphenylacetic acid a potential biomarker for the consumption of these foods. 3-Hydroxyphenylacetic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and colorectal cancer; 3-hydroxyphenylacetic acid has also been linked to the inborn metabolic disorder phenylketonuria. Based on a literature review a significant number of articles have been published on 3-Hydroxyphenylacetic acid.

CAS Number

621-37-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(m-Hydroxyphenyl)acetic acid	ChEBI
3-Hydroxybenzeneacetic acid	ChEBI
m-Hydroxyphenylacetic acid	ChEBI
(m-Hydroxyphenyl)acetate	Generator
3-Hydroxybenzeneacetate	Generator
m-Hydroxyphenylacetate	Generator
3-Hydroxyphenylacetate	Generator
(3-Hydroxy-phenyl)-acetate	HMDB
(3-Hydroxy-phenyl)-acetic acid	HMDB
3-Hydroxy-benzeneacetate	HMDB
3-Hydroxy-benzeneacetic acid	HMDB
Meta-hydroxyphenylacetic acid	HMDB
3'-Hydroxyphenylacetic acid	HMDB
2-(3-Hydroxyphenyl)acetic acid	HMDB
3-Hydroxyphenylacetic acid	KEGG
(3-hydroxy-phenyl)-acetate	hmdb
(3-hydroxy-phenyl)-acetic acid	hmdb
3-hydroxy-benzeneacetate	hmdb
3-hydroxy-benzeneacetic acid	hmdb
m-hydroxyphenylacetate	hmdb
m-hydroxyphenylacetic acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	6.98 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	14.78 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-(3-hydroxyphenyl)acetic acid

InChI Identifier

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

InChI Key

FVMDYYGIDFPZAX-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

Classification

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
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:17445 )
phenols (CHEBI:17445 )

Ontology

Klebsiella pneumoniae

Clostridium:

Clostridium species

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

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 - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
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
GC-MS	3-Hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrum	splash10-03di-1940000000-6378ab49a38d6170a2c7	Spectrum
GC-MS	3-Hydroxyphenylacetic acid, 3 TMS, GC-MS Spectrum	splash10-0a4l-2970000000-c0a0a7b13f6da1df88aa	Spectrum
GC-MS	3-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0950000000-26683d1d8cf72cac5bc1	Spectrum
GC-MS	3-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-03di-1940000000-6378ab49a38d6170a2c7	Spectrum
GC-MS	3-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0a4l-2970000000-c0a0a7b13f6da1df88aa	Spectrum
GC-MS	3-Hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-01ot-0920000000-fe0044d1e19c78b17eb6	Spectrum
Predicted GC-MS	3-Hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-4900000000-6172123969b2e568c06a	Spectrum
Predicted GC-MS	3-Hydroxyphenylacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-5930000000-ac6c8b167a6f6d3d0521	Spectrum
Predicted GC-MS	3-Hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyphenylacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyphenylacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyphenylacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyphenylacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-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)	splash10-0a4i-0900000000-64f3b80f6fa4b2ca0d3a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-066r-9600000000-cd1ada1ac0e33b3478b8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-066r-9300000000-6a96a42ca7818fbc430d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0900000000-acff5d00da3be2a5c74a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-97c0564c13ebd3284f50	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3900000000-a80e9eddf44bc0095f79	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-96b630f0c24804af9aee	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00mo-9000000000-3efd8d8db4dc2eae90dd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0fb9-2900000000-f3873a7ac7ad570e403d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9100000000-e90d6c5d8bf401d57e4e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-ce3129eea4958f02c7b6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000f-9400000000-a325a8a905a878e9c037	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-ca93ecdc5cf66e6d1291	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-b499e6492f74c3b1cd54	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-95cdec832fdad733908a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052b-9600000000-17540945d3efb5ed0aee	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00ou-9300000000-9803bf9d8616a80e7c46	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-0900000000-7f6b0589d86943d38ebf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0gdl-9000000000-7b58085ace82f3720778	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-2c8a7cef25cc353fd182	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-0900000000-3df834bace0a8802e668	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kto-9600000000-42568fc5a5b34539aa51	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-163da322055a76a2c202	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-0900000000-06fd2ca96cf98a192ad7	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-2900000000-d43171f0cd0bce73a080	2017-06-28	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, 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, 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
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum