4-Hydroxyphenylacetic acid (YMDB01486)

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Identification

YMDB ID

YMDB01486

Name

4-Hydroxyphenylacetic acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

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 a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(4-hydroxy-phenyl)-acetate
(4-hydroxy-phenyl)-acetic acid
(4-Hydroxy-phenyl)-essigsaeure
(4-hydroxyphenyl)acetate
(4-hydroxyphenyl)acetic acid
(o-hydroxyphenyl)acetic acid
(p-hydroxyphenyl)-Acetate
(p-hydroxyphenyl)-Acetic acid
(p-Hydroxyphenyl)acetate
(p-Hydroxyphenyl)acetic acid
4-carboxymethylphenol
4-Hydroxy-Benzeneacetate
4-Hydroxy-Benzeneacetic acid
4-Hydroxybenzeneacetate
4-Hydroxybenzeneacetic acid
4-hydroxyphenylacetate
4-Hydroxyphenylacetic acid
Acetic acid, (p-hydroxyphenyl)-
Benzeneacetic acid, 4-hydroxy-
p-hydroxyphenylacetate
p-hydroxyphenylacetic acid
Parahydroxy phenylacetate
Parahydroxy phenylacetic acid
Parahydroxyphenylacetate
4-Hydroxyphenyl-acetic acid
Para-hydroxyphenylacetic acid
4'-Hydroxyphenylacetic acid
2-(4-Hydroxyphenyl)acetic acid

CAS number

156-38-7

Weight

Average: 152.1473
Monoisotopic: 152.047344122

InChI Key

XQXPVVBIMDBYFF-UHFFFAOYSA-N

InChI

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

IUPAC Name

2-(4-hydroxyphenyl)acetic acid

Traditional IUPAC Name

4-hydroxyphenylacetic acid

Chemical Formula

C₈H₈O₃

SMILES

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

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
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 )

Physical Properties

State

Solid

Charge

Melting point

148-150 °C

Experimental Properties

Property	Value	Reference
Water Solubility	60.7 mg/mL at 25 oC [GRACIN,S & RASMUSON,AC (2002)]	PhysProp
LogP	0.75 [HANSCH,C ET AL. (1995)]	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Phenylalanine metabolism	PW002437
Tyrosine metabolism	PW002441

KEGG Pathways

Phenylalanine metabolism	ec00360
Tyrosine metabolism	ec00350

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-01ta-1930000000-57c9e8ddaa10569055aa	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0h01-0940000000-a14203384331e709252f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-03fs-1930000000-80c21819072fb01958dc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9410000000-678591f03aba45c2a6ae	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0h0r-2940000000-760b6c506072a61059c0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-2900000000-3939c62b0d7f649ff402	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-fdb73325a31c758496e9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0gyk-0980000000-ed36f36969e4d51b9a8d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01ta-1930000000-57c9e8ddaa10569055aa	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0h01-0940000000-a14203384331e709252f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03fs-1930000000-80c21819072fb01958dc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9410000000-678591f03aba45c2a6ae	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h0r-2940000000-760b6c506072a61059c0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03fs-1931100000-50456fed0c5ef95ecb57	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-b6f6363476ffa290862f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-5930000000-abf5245dd22d012d04f8	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0pb9-0900000000-e3dfb4b180d858b3a854	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-056r-9400000000-9a6cb39e019a0b40a666	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0kdl-9400000000-35ecc22161defddc7b21	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-0a4i-2900000000-3939c62b0d7f649ff402	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0a4i-6900000000-fdb73325a31c758496e9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-4900000000-88da569804a98e1a99ea	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9300000000-eef23e2f30d876f4a1f9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-0a95379b7cea57386b0b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0zfr-0900000000-369a695f2c7bcf3a4a5c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-4900000000-88da569804a98e1a99ea	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9300000000-eef23e2f30d876f4a1f9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-0a95379b7cea57386b0b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-dd0a48d9d6528f6a0a6a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0900000000-02cd23fa5ff37594d2be	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0900000000-bbac468eb7ce6ea99123	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-1900000000-05d18e7bb4163e35e2aa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-1900000000-9a0086561d6f8a169670	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-398dff08b5b2a56e658c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-5f75ea6de2d6bad624d8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9700000000-68d0f4a3b2f7ccfcc2a4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-7ce02fea5a9ef38024f2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-0900000000-12e388b0927ed1c6e166	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-2900000000-ae1870eee4853c57a447	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-3900000000-3be1d4a7c16ea7a3eee1	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Yannai S. Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Chapman & Hall/CRC; 2004.

Synthesis Reference:

Qiao, Xi-long; Tian, Hui; Li, Wen; Zhao, Xiu-yun; Zhang, Jin-fang. Study of 4-hydroxyphenylacetic acid synthesis from glyoxalic acid. Hebei Gongye Keji (2005), 22(5), 264-266.

External Links:

Resource	Link
CHEBI ID	18101
HMDB ID	HMDB00020
Pubchem Compound ID	127
Kegg ID	C00642
ChemSpider ID	124
FOODB ID	FDB010534
Wikipedia	4-Hydroxyphenylacetic_acid
BioCyc ID	4-HYDROXYPHENYLACETATE

Structure for #<Compound:0xa200c6b4>