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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-02-26 19:02:50 UTC

Update Date

2023-02-21 17:29:21 UTC

HMDB ID

HMDB0059763

Secondary Accession Numbers

HMDB59763

Metabolite Identification

Common Name

3,4-Dimethoxybenzoic acid

Description

3,4-Dimethoxybenzoic acid, also known as 3,4-dimethylprotocatechuate or veratric acid, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. 3,4-Dimethoxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,4-Dimethoxybenzoic acid has been detected, but not quantified in, corianders and olives. This could make 3,4-dimethoxybenzoic acid a potential biomarker for the consumption of these foods. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12    4                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Dimethylprotocatechuic acid	ChEBI
Dimethylprotocatechuic acid	ChEBI
Veratric acid	ChEBI
Veratrumenoic acid	ChEBI
Veratrylic acid	ChEBI
3,4-Dimethylprotocatechuate	Generator
Dimethylprotocatechuate	Generator
Veratrate	Generator
Veratrumenoate	Generator
Veratrylate	Generator
3,4-Dimethoxybenzoate	Generator
Veratric acid, potassium salt	MeSH
Veratric acid, sodium salt	MeSH
Veratric acid, sodium salt, (11)C-labeled	MeSH
3,4-Dimethoxybenzoic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

3,4-dimethoxybenzoic acid

Traditional Name

veratric acid

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C9H10O4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3,(H,10,11)

InChI Key

DAUAQNGYDSHRET-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

P-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

P-methoxybenzoic acid or derivatives
M-methoxybenzoic acid or derivatives
O-dimethoxybenzene
Dimethoxybenzene
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoic acids (CHEBI:296881 )

Ontology

Not Available

Coriander (FooDB: FOOD00061)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.64 g/L	ALOGPS
logP	1.52	ALOGPS
logP	1.32	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.24 m³·mol⁻¹	ChemAxon
Polarizability	17.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	142.875	31661259
DarkChem	[M-H]-	141.834	31661259
DeepCCS	[M+H]+	138.2	30932474
DeepCCS	[M-H]-	134.373	30932474
DeepCCS	[M-2H]-	171.628	30932474
DeepCCS	[M+Na]+	147.167	30932474
AllCCS	[M+H]+	139.1	32859911
AllCCS	[M+H-H2O]+	134.9	32859911
AllCCS	[M+NH4]+	143.1	32859911
AllCCS	[M+Na]+	144.2	32859911
AllCCS	[M-H]-	137.4	32859911
AllCCS	[M+Na-2H]-	138.3	32859911
AllCCS	[M+HCOO]-	139.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dimethoxybenzoic acid	COC1=C(OC)C=C(C=C1)C(O)=O	2707.5	Standard polar	33892256
3,4-Dimethoxybenzoic acid	COC1=C(OC)C=C(C=C1)C(O)=O	1553.7	Standard non polar	33892256
3,4-Dimethoxybenzoic acid	COC1=C(OC)C=C(C=C1)C(O)=O	1679.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dimethoxybenzoic acid,1TMS,isomer #1	COC1=CC=C(C(=O)O[Si](C)(C)C)C=C1OC	1707.1	Semi standard non polar	33892256
3,4-Dimethoxybenzoic acid,1TBDMS,isomer #1	COC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1OC	1946.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxybenzoic acid EI-B (Non-derivatized)	splash10-001i-6900000000-4a8e98b69d84f09a207d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxybenzoic acid EI-B (Non-derivatized)	splash10-001i-4900000000-cb469c325f86dcaebb63	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxybenzoic acid EI-B (Non-derivatized)	splash10-001i-6900000000-4a8e98b69d84f09a207d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxybenzoic acid EI-B (Non-derivatized)	splash10-001i-4900000000-cb469c325f86dcaebb63	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethoxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fs9-1900000000-7b7b6ee16c41bbeb8ea7	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethoxybenzoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9660000000-f0ac17b7c31703cdd68b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethoxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethoxybenzoic 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 - 3,4-Dimethoxybenzoic acid Linear Ion Trap , negative-QTOF	splash10-000i-0900000000-b278ebee06358e45a484	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid Linear Ion Trap , negative-QTOF	splash10-000i-0900000000-65cc74d2e20865936db9	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 10V, Positive-QTOF	splash10-001i-0900000000-68319718835cc95c3de1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 20V, Positive-QTOF	splash10-001i-0900000000-3112f03abf5146b7fdbc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 40V, Positive-QTOF	splash10-0ff1-6900000000-ed8884f3fcc1216b34a3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 10V, Negative-QTOF	splash10-001i-0900000000-6b3b62b879aa4d5e208e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 20V, Negative-QTOF	splash10-0080-0900000000-10547cd32070770340ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 40V, Negative-QTOF	splash10-05ir-7900000000-c21b16fa3776d4007851	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 10V, Positive-QTOF	splash10-000i-0900000000-c50ac015643e0db698cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 20V, Positive-QTOF	splash10-0019-0900000000-796d5f48c5cee4880d65	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 40V, Positive-QTOF	splash10-0ff0-9600000000-ae900b44493c1d073437	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 10V, Negative-QTOF	splash10-001i-0900000000-49a059652c5c432bc06e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 20V, Negative-QTOF	splash10-000i-0900000000-2d692dbb4687b9ffd794	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 40V, Negative-QTOF	splash10-052f-9300000000-cf393361be800fb908b2	2021-09-22	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

419

FooDB ID

FDB000222

KNApSAcK ID

Not Available

Chemspider ID

6854

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7121

PDB ID

TWO

ChEBI ID

296881

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Shin SW, Jung E, Kim S, Lee KE, Youm JK, Park D: Antagonist effects of veratric acid against UVB-induced cell damages. Molecules. 2013 May 10;18(5):5405-19. doi: 10.3390/molecules18055405. [PubMed:23666007 ]
Pham NH, Baldo BA, Manfredi M, Zerboni R: Fine structural specificity differences of trimethoprim allergenic determinants. Clin Exp Allergy. 1996 Oct;26(10):1155-60. [PubMed:8911701 ]

Showing metabocard for 3,4-Dimethoxybenzoic acid (HMDB0059763)

MOL for HMDB0059763 (3,4-Dimethoxybenzoic acid)

3D MOL for HMDB0059763 (3,4-Dimethoxybenzoic acid)

3D SDF for HMDB0059763 (3,4-Dimethoxybenzoic acid)

3D-SDF for HMDB0059763 (3,4-Dimethoxybenzoic acid)

PDB for HMDB0059763 (3,4-Dimethoxybenzoic acid)

3D PDB for HMDB0059763 (3,4-Dimethoxybenzoic acid)

SMILES for HMDB0059763 (3,4-Dimethoxybenzoic acid)

INCHI for HMDB0059763 (3,4-Dimethoxybenzoic acid)

Structure for HMDB0059763 (3,4-Dimethoxybenzoic acid)

3D Structure for HMDB0059763 (3,4-Dimethoxybenzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra