AFCDB: Gentisic acid (FDB000844)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:44 UTC

Update date

2020-09-17 15:38:22 UTC

Primary ID

FDB000844

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Gentisic acid

Description

Gentisic acid, also known as gentisate or 2,5-dioxybenzoate, 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. A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions. Gentisic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gentisic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Gentisic acid is found, on average, in the highest concentration within a few different foods, such as tarragons, common thymes, and common sages and in a lower concentration in lemon balms, parsley, and soy beans. Gentisic acid has also been detected, but not quantified in, several different foods, such as garden tomato (var.), cocoa beans, spearmints, common pea, and carrots. This could make gentisic acid a potential biomarker for the consumption of these foods.

CAS Number

490-79-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0f79-7900000000-4ac54ba9a72c8707055d	2015-03-01	View Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0849000000-d6f7b541cabdb5e20dd6	Spectrum
GC-MS	Gentisic acid, 3 TMS, GC-MS Spectrum	splash10-0a4i-3955000000-215d684d2fae395f2e76	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-03di-2009080030-be174b5f8728c96650e7	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0229000000-a4712abe7c7db86a97be	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0849000000-d6f7b541cabdb5e20dd6	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-3955000000-215d684d2fae395f2e76	Spectrum
GC-MS	Gentisic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-1946000000-be25f693c540abb01bde	Spectrum
Predicted GC-MS	Gentisic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-114r-2900000000-c5a4c512f555f4ebce47	Spectrum
Predicted GC-MS	Gentisic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-008a-5092000000-1b91af6751ccb58c613c	Spectrum
Predicted GC-MS	Gentisic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Gentisic acid, TBDMS_3_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)	splash10-0zfr-0900000000-816a84a65cefa1b31731	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-1900000000-977e85749e8fa31315c5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-1900000000-086d66fbe2d41a2d725c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-e3a62163a69461ab2cff	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-0900000000-06431a9cf0c877732fe5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-0900000000-e938fddf26a9bb2cd9e3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-0900000000-38ef6d9660431bec9b3b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-0900000000-ac95d834c95477f325a7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative	splash10-0udi-0902000000-6cc114aa94b58c53c123	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - MALDI-TOF (Voyager DE-PRO, Applied Biosystems) , Negative	splash10-0udi-0901000000-077381dba9d80706a097	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0900000000-56fe39ec90c2e54662db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pdi-0439000000-d097f2b9a5189bc4bb0f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0900000000-ddf5ec6162fb4b835c3a	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-e3a62163a69461ab2cff	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-06431a9cf0c877732fe5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-e938fddf26a9bb2cd9e3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-38ef6d9660431bec9b3b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-ac95d834c95477f325a7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0900000000-56fe39ec90c2e54662db	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0a4i-0900000000-a0b5d2185d831113c59a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0a4i-0900000000-ddf5ec6162fb4b835c3a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-beeea2764ef314b28b6f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-8f8c308c2151437089c1	2021-09-20	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, 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, 600 MHz, H₂O, experimental)	Spectrum

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.

Gentisic acid (FDB000844)

Structure for FDB000844 (Gentisic acid)