Showing Compound 3,5-Dihydroxy-4-methoxybenzoic acid (FDB001960)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:11 UTC

Update date

2019-11-26 02:56:49 UTC

Primary ID

FDB001960

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3,5-Dihydroxy-4-methoxybenzoic acid

Description

4-O-Methyl gallic acid (4-OMGA) has first been identified as a major methyl derivative of gallic acid in human plasma and urine. More recently, 4-O-methyl gallic acid (4-OMGA) has been found in urine during regular black tea ingestion and in plasma after moderate red wine consumption. PMID: 15527792 4-O-methylgallic acid (4-OMGA), a major metabolite of gallic acid abundant in red wine. 4-OMGA inhibited the expression of intercellular adhesion molecule-1(ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) in human umbilical vein endothelial cells (HUVECs) stimulated with tumor necrosis factor-alpha (TNF-alpha), resulting in the suppression of leukocyte adhesion to HUVECs. PMID: 17027748 [HMDB]

CAS Number

4319-02-2

Structure

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

Synonyms

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Synonym	Source
3,5-Dihydroxy-4-methoxy-benzoate	HMDB
3,5-Dihydroxy-4-methoxy-benzoic acid	HMDB
3,5-Dihydroxy-4-methoxybenzoate	HMDB, Generator
3,5-Dihydroxy-4-methoxybenzoic acid	MeSH
3,5-Dihydroxy-P-anisic acid	HMDB
4-Methoxy-3,5-dihydroxybenzoate	HMDB
4-Methoxy-3,5-dihydroxybenzoic acid	MeSH
4-Methoxygallate	Generator, HMDB
4-Methoxygallic acid	MeSH
4-O-Methylgallate	Generator

Showing 1 to 10 of 54 entries

Predicted Properties

Property	Value	Source
Water Solubility	4.93 g/L	ALOGPS
logP	1.32	ALOGPS
logP	0.87	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.74 m³·mol⁻¹	ChemAxon
Polarizability	16.72 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

Chemical Formula

C8H8O5

IUPAC name

3,5-dihydroxy-4-methoxybenzoic acid

InChI Identifier

InChI=1S/C8H8O5/c1-13-7-5(9)2-4(8(11)12)3-6(7)10/h2-3,9-10H,1H3,(H,11,12)

InChI Key

UBXDWYFLYYJQFR-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(O)C=C(C=C1O)C(O)=O

Average Molecular Weight

184.1461

Monoisotopic Molecular Weight

184.037173366

Classification

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
Methoxyphenol
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Resorcinol
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
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

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Plant

Fungi:

Beauveria:

Beauveria sulfurescens

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 52.18%; H 4.38%; O 43.44%	DFC
Melting Point	Mp 246°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	3,5-Dihydroxy-4-methoxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0159-1900000000-32a93cf4f7568a9bdedc	Spectrum
Predicted GC-MS	3,5-Dihydroxy-4-methoxybenzoic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-009i-2139000000-adf8b88e8bb85a43cb0f	Spectrum
Predicted GC-MS	3,5-Dihydroxy-4-methoxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-a129a3b3cfd0493a0408	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-4576c6e0e594b56d93b5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-2900000000-19f8938cc76bae18f2e9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-886cb3b61676c31904a2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0080-0900000000-4bad45b0a4df1de7f271	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xr-2900000000-17d90b668a07c63b811e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-25175f7a5af29e8cfca5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0900000000-f2f0c47926cb84d06fdd	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05n0-9000000000-eb7116993f3b670a52cf	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-962a559c43543c7fb0cb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-0900000000-4cfc053bdff3ca1768bb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9200000000-548c94ddc8cc64cba53b	2021-09-24	View Spectrum