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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-04-03 14:10:30 UTC

Update Date

2023-02-21 17:18:00 UTC

HMDB ID

HMDB0013676

Secondary Accession Numbers

HMDB13676

Metabolite Identification

Common Name

2,6-Dihydroxybenzoic acid

Description

2,6-Dihydroxybenzoic acid, also known as 6-hydroxysalicylic acid or gamma-resorcylic acid, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. 2,6-Dihydroxybenzoic acid is found, on average, in the highest concentration within beer and olives (Olea europaea). 2,6-Dihydroxybenzoic acid has also been detected, but not quantified in, strawberries (Fragaria X ananassa). This could make 2,6-dihydroxybenzoic acid a potential biomarker for the consumption of these foods. 2,6-Dihydroxybenzoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2,6-Dihydroxybenzoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Hydroxysalicylic acid	ChEBI
gamma-Resorcylic acid	ChEBI
6-Hydroxysalicylate	Generator
g-Resorcylate	Generator
g-Resorcylic acid	Generator
gamma-Resorcylate	Generator
Γ-resorcylate	Generator
Γ-resorcylic acid	Generator
2,6-Dihydroxybenzoate	Generator
2,6-Dihydroxy-benzoic acid	HMDB
2,6-Dihydroxybenzoic acid (acd/name 4.0)	HMDB
2,6-Resorcylic acid	HMDB
2-Carboxyresorcinol	HMDB
Benzoate	HMDB
Benzoic acid	HMDB

Chemical Formula

C₇H₆O₄

Average Molecular Weight

154.121

Monoisotopic Molecular Weight

154.026608673

IUPAC Name

2,6-dihydroxybenzoic acid

Traditional Name

2,6-dihydroxybenzoic acid

CAS Registry Number

303-07-1

SMILES

OC(=O)C1=C(O)C=CC=C1O

InChI Identifier

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

InChI Key

AKEUNCKRJATALU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acids

Alternative Parents

Substituents

Salicylic acid
Benzoic acid
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydroxybenzoic acid (CHEBI:68465 )

Ontology

Not Available

Exogenous (HMDB: HMDB0013676)

Food

Fruit

Berry

Strawberry (FooDB: FOOD00083)

Herb and spice

Oilseed crop

Evening primrose (FooDB: FOOD00120)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 °C	Not Available
Boiling Point	343.66 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	9.56 mg/mL	Not Available
LogP	2.20	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.49 g/L	ALOGPS
logP	1.28	ALOGPS
logP	2.32	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-6	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	13.67 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.589	31661259
DarkChem	[M-H]-	126.754	31661259
DeepCCS	[M+H]+	133.046	30932474
DeepCCS	[M-H]-	130.579	30932474
DeepCCS	[M-2H]-	166.493	30932474
DeepCCS	[M+Na]+	141.432	30932474
AllCCS	[M+H]+	132.7	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	137.0	32859911
AllCCS	[M+Na]+	138.2	32859911
AllCCS	[M-H]-	125.7	32859911
AllCCS	[M+Na-2H]-	127.0	32859911
AllCCS	[M+HCOO]-	128.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dihydroxybenzoic acid	OC(=O)C1=C(O)C=CC=C1O	2563.6	Standard polar	33892256
2,6-Dihydroxybenzoic acid	OC(=O)C1=C(O)C=CC=C1O	1528.8	Standard non polar	33892256
2,6-Dihydroxybenzoic acid	OC(=O)C1=C(O)C=CC=C1O	1397.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dihydroxybenzoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(O)C=CC=C1O	1550.6	Semi standard non polar	33892256
2,6-Dihydroxybenzoic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(O)=C1C(=O)O	1603.2	Semi standard non polar	33892256
2,6-Dihydroxybenzoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(O)C=CC=C1O[Si](C)(C)C	1631.6	Semi standard non polar	33892256
2,6-Dihydroxybenzoic acid,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C)=C1C(=O)O	1648.9	Semi standard non polar	33892256
2,6-Dihydroxybenzoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C(O[Si](C)(C)C)C=CC=C1O[Si](C)(C)C	1762.7	Semi standard non polar	33892256
2,6-Dihydroxybenzoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(O)C=CC=C1O	1793.6	Semi standard non polar	33892256
2,6-Dihydroxybenzoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(O)=C1C(=O)O	1872.2	Semi standard non polar	33892256
2,6-Dihydroxybenzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(O)C=CC=C1O[Si](C)(C)C(C)(C)C	2105.2	Semi standard non polar	33892256
2,6-Dihydroxybenzoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)O	2181.7	Semi standard non polar	33892256
2,6-Dihydroxybenzoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1O[Si](C)(C)C(C)(C)C	2411.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dihydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w2i-4900000000-e371483679ffb975b0b7	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dihydroxybenzoic acid GC-MS (3 TMS) - 70eV, Positive	splash10-05gi-5092000000-75920741b3da9d472393	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dihydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dihydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 10V, Negative-QTOF	splash10-0zfr-0900000000-047fb76c7edd9d8a1a11	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 20V, Negative-QTOF	splash10-0aor-9800000000-bd52d2bc7f788640b45e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 40V, Negative-QTOF	splash10-0006-9000000000-cdef27f177ed57f154f5	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 10V, Positive-QTOF	splash10-0a4r-0900000000-d899ed75ac04fcbce213	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 20V, Positive-QTOF	splash10-000i-0900000000-61b442ba35921bf15903	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 40V, Positive-QTOF	splash10-00kr-9700000000-af21042a1145ed08d24f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 10V, Negative-QTOF	splash10-0pb9-0900000000-b2d93bd5c6cc2201063c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 20V, Negative-QTOF	splash10-0a4i-0900000000-b40aa1f15c5c8ca99961	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 40V, Negative-QTOF	splash10-0a4i-7900000000-d0ea5ade866525499246	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 10V, Positive-QTOF	splash10-000i-0900000000-1d3dc5a6ec26910a12df	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 20V, Positive-QTOF	splash10-000i-2900000000-2405474149bdbe719ff7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 40V, Positive-QTOF	splash10-0pvr-9500000000-3b04c7ddb3ecbcc8f3af	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 10V, Negative-QTOF	splash10-0a4r-0900000000-c5748c55776248a64a56	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 20V, Negative-QTOF	splash10-0a4i-3900000000-0d33dcb468f21e33c8b6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dihydroxybenzoic acid 40V, Negative-QTOF	splash10-014i-9100000000-2081dc4c4961d29b4fff	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.014 +/- 0.008 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.011 +/- 0.003 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.022 +/- 0.008 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.026 +/- 0.007 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.012 +/- 0.005 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.005 +/- 0.002 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.01 +/- 0.003 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.009 +/- 0.002 uM	Adult (>18 years old)	Male	Normal	19812218	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.09 +/- 0.057 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

CPD-8816

BiGG ID

Not Available

Wikipedia Link

2,6-Dihydroxybenzoic_acid

METLIN ID

Not Available

PubChem Compound

9338

PDB ID

GRE

ChEBI ID

68465

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1166771

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]

Showing metabocard for 2,6-Dihydroxybenzoic acid (HMDB0013676)

MOL for HMDB0013676 (2,6-Dihydroxybenzoic acid)

3D MOL for HMDB0013676 (2,6-Dihydroxybenzoic acid)

3D SDF for HMDB0013676 (2,6-Dihydroxybenzoic acid)

3D-SDF for HMDB0013676 (2,6-Dihydroxybenzoic acid)

PDB for HMDB0013676 (2,6-Dihydroxybenzoic acid)

3D PDB for HMDB0013676 (2,6-Dihydroxybenzoic acid)

SMILES for HMDB0013676 (2,6-Dihydroxybenzoic acid)

INCHI for HMDB0013676 (2,6-Dihydroxybenzoic acid)

Structure for HMDB0013676 (2,6-Dihydroxybenzoic acid)

3D Structure for HMDB0013676 (2,6-Dihydroxybenzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra