Bovine Metabolome Database: Showing metabocard for p-Hydroxymandelic acid (BMDB0000822)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:37:07 UTC

Update Date

2020-05-11 20:57:33 UTC

BMDB ID

BMDB0000822

Secondary Accession Numbers

BMDB00822

Metabolite Identification

Common Name

p-Hydroxymandelic acid

Description

p-Hydroxymandelic acid, also known as 4-hydroxymandelate or 4-hydroxyphenylglycolate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Based on a literature review a significant number of articles have been published on p-Hydroxymandelic acid.

Structure

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

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 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	103 - 106 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1970000000-156d51ef8c0ad0f76d64	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1970000000-156d51ef8c0ad0f76d64	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-8900000000-b062f43216386832dded	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-014i-1091000000-70622b0e5331b2fe290f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-34b31ac9e80ec28f0bbc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-4900000000-776e3b6ee256d0fe5cb4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-4900000000-9dd6f152de533ac938a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-415c5d4c2ea88934e2c4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-0900000000-9c790106a25e9dd43e94	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9300000000-73afdd4e3b6cbc4726e9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-48da404afde1f15d2691	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0v4i-0900000000-da456e31e91f9a9b7c34	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-bb2667f5c8ef34847d41	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fv-9600000000-c7c25ea1fa9244b02d82	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-0900000000-0853088e78547b002394	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00r7-4900000000-4fd0952fc81ec79b040f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-6c7af63bb32592f280fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0v4i-0900000000-bc65c2527a8df7d8147a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pba-4900000000-9f3e7769f03e19541e95	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-3bd2d0f928f8e1b0e0b4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-4900000000-a948bbe144908fb34a34	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0596-5900000000-a99429838637eb5a45ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-a202d17e840c1184fce5	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Liver
Retina
Vitreous Humour

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Retina	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Vitreous Humour	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

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

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for p-Hydroxymandelic acid (BMDB0000822)

Structure for BMDB0000822 (p-Hydroxymandelic acid)