Showing Compound Gentisic acid (FDB000844)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:44 UTC

Update date

2019-11-26 02:55:30 UTC

Primary ID

FDB000844

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Gentisic acid

Description

Gentisic acid is a dihydroxybenzoic acid. It is a crystalline powder that forms monoclinic prism in water solution. Gentisic acid is an active metabolite of salicylic acid degradation. There is an increasing amount of evidence indicating that gentisic acid has a broad spectrum of biological activity, such as anti-inflammatory, antirheumatic and antioxidant properties. Gentisic acid is also a byproduct of tyrosine and benzoate metabolism. [HMDB]. Gentisic acid is found in many foods, some of which are common sage, common grape, nutmeg, and dill.

CAS Number

490-79-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2,5-Dihydroxybenzoate	ChEBI
5-Hydroxysalicylic acid	ChEBI
Gentisate	ChEBI
Hydroquinonecarboxylic acid	ChEBI
2,5-Dihydroxybenzoic acid	Kegg
5-Hydroxysalicylate	Generator
Hydroquinonecarboxylate	Generator
2,5-Dioxybenzoate	HMDB
2,5-Dioxybenzoic acid	HMDB
3,6-Dihydroxybenzoate	HMDB
3,6-Dihydroxybenzoic acid	HMDB
5-Hydroxy-salicylate	HMDB
5-Hydroxy-salicylic acid	HMDB
Carboxyhydroquinone	HMDB
Dihydroxybenzoicacid	HMDB
Gensigen	HMDB
Gensigon	HMDB
Gentisinate	HMDB
Gentisinic acid	HMDB
2,5-Dihydroxybenzoic acid, monosodium salt	HMDB
Lithium 2,5-dihydroxybenzoate	HMDB
Gentisic acid	ChEBI
Gentisic acid, 8CI, INN	db_source
Hydroxyquinonecarboxylic acid	db_source

Predicted Properties

Property	Value	Source
Water Solubility	12.3 g/L	ALOGPS
logP	1.23	ALOGPS
logP	1.67	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.53	ChemAxon
pKa (Strongest Basic)	-5.9	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	1	ChemAxon
Refractivity	37.28 m³·mol⁻¹	ChemAxon
Polarizability	13.78 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

Chemical Formula

C7H6O4

IUPAC name

2,5-dihydroxybenzoic acid

InChI Identifier

InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)

InChI Key

WXTMDXOMEHJXQO-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

154.121

Monoisotopic Molecular Weight

154.026608673

Classification

Description

belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Dihydroxybenzoic acid
Salicylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Benzoic acid
Benzoyl
Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydroxybenzoic acid (CHEBI:17189 )

Ontology

Physiological effect

Health effect:

Health condition:

Idiopathic oro-facial pain

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Fungi

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 54.55%; H 3.92%; O 41.52%	DFC
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

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0849000000-d6f7b541cabdb5e20dd6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0a4i-3955000000-215d684d2fae395f2e76	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-2009080030-be174b5f8728c96650e7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-0229000000-a4712abe7c7db86a97be	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0849000000-d6f7b541cabdb5e20dd6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-3955000000-215d684d2fae395f2e76	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-1946000000-be25f693c540abb01bde	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-114r-2900000000-c5a4c512f555f4ebce47	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-008a-5092000000-1b91af6751ccb58c613c	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0zfr-0900000000-816a84a65cefa1b31731	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-1900000000-977e85749e8fa31315c5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-1900000000-086d66fbe2d41a2d725c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-e3a62163a69461ab2cff	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-0900000000-06431a9cf0c877732fe5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-0900000000-e938fddf26a9bb2cd9e3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-0900000000-38ef6d9660431bec9b3b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-0900000000-ac95d834c95477f325a7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positive	splash10-004r-1913000000-eba82100caa3c2664508	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative	splash10-0udi-0902000000-6cc114aa94b58c53c123	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positive	splash10-0k9i-0930000000-4388abc8fe86bc940e89	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative	splash10-0udi-0901000000-077381dba9d80706a097	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Positive	splash10-0fri-0930000000-4e24b1261f33fba704e2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000b-9800000000-35424c6ac43370b30b89	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0900000000-56fe39ec90c2e54662db	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0900000000-ddf5ec6162fb4b835c3a	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-0fe66ae910e6a6a75fd0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0900000000-92d150f8439f22e9e2bb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a7i-9400000000-b1783532af734cb7e8c4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-64a4c14f26bc9fcf8dfa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-acfcb8c4421ee8a0c31c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-4900000000-dd5469400fff82ccc358	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0f79-7900000000-4ac54ba9a72c8707055d	JSpectraViewer \| MoNA
1D NMR	1H 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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

416

DrugBank ID

Not Available

HMDB ID

HMDB00152

CRC / DFC (Dictionary of Food Compounds) ID

BJR95-G:BJR95-G

EAFUS ID

Not Available

Dr. Duke ID

2,5-DIHYDROXYBENZOIC-ACID|GENTISIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00002648

HET ID

GTQ

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Gentisic_acid

Phenol-Explorer Metabolite ID

416

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

Descriptor	ID	Definition	Reference
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti feedant			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti rheumatic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Gentisic acid (FDB000844)

Structure for FDB000844 (Gentisic acid)