Showing Compound Methyl gallate (FDB000663)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:39 UTC

Update date

2019-11-26 02:55:10 UTC

Primary ID

FDB000663

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methyl gallate

Description

Methyl gallate, also known as methyl 3 or methyl galloic acid, is a member of the class of compounds known as galloyl esters. Galloyl esters are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. Methyl gallate is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Methyl gallate can be found in peach and pomegranate, which makes methyl gallate a potential biomarker for the consumption of these food products. Methyl gallate is a phenolic compound. It is the methyl ester of gallic acid .

CAS Number

99-24-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Methyl gallic acid	Generator
Methyl 3	ChEMBL
45-Trihydroxybenzoate	ChEMBL
Methyl galloate	ChEMBL
345-Trihydroxy-benzoic acid methyl ester	ChEMBL
45-Trihydroxybenzoic acid	Generator
Methyl galloic acid	Generator
345-Trihydroxy-benzoate methyl ester	Generator
Gallic acid, methyl ester	MeSH
Methyl 3,4,5-trihydroxybenzoate	MeSH
3,4,5-Trihydroxy-benzoic acid methyl ester	biospider
Benzoic acid, 3,4,5-trihydroxy-, methyl ester	biospider
Gallic acid methyl ester	biospider
Gallicin?	db_source
Methyl gallate	db_source
Methylgallate	biospider

Predicted Properties

Property	Value	Source
Water Solubility	4.11 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.07	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.03 m³·mol⁻¹	ChemAxon
Polarizability	16.99 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

methyl 3,4,5-trihydroxybenzoate

InChI Identifier

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

InChI Key

FBSFWRHWHYMIOG-UHFFFAOYSA-N

Isomeric SMILES

COC(=O)C1=CC(O)=C(O)C(O)=C1

Average Molecular Weight

184.1461

Monoisotopic Molecular Weight

184.037173366

Classification

Description

Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 52.18%; H 4.38%; O 43.44%	DFC
Melting Point	Mp 157°	DFC
Boiling Point	Not Available
Experimental Water Solubility	10.6 mg/mL	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	0.86	HANSCH,C ET AL. (1995)
Experimental pKa	pKa1 7.88 (25°, 0.1M KNO3)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	283 () (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Methyl gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ufr-0900000000-72baa95f31204513dc9d	Spectrum
Predicted GC-MS	Methyl gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl gallate, 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 - 35V, Positive	splash10-0006-9700000000-11744c62170a98354cbc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-1900000000-d6261b21dc9a9fd566b9	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-401d71dbf57a34ddc235	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-0900000000-51202d68563eee1bdab2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvj-5900000000-b7c5629192d45e0d9cb1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-90389cc7f792df061dc3	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-50a11e1df989b937ae23	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uk9-5900000000-59e6084d7e7bb182a1a7	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-fc79f14d18e4e34433ab	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fc0-1900000000-16bd999e2e402d7a0912	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-067l-9300000000-e54d0ca66a63d30da4f1	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-366cfe98e3457a4b68f3	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-1900000000-5526e088c3d9034b9235	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gds-9300000000-b3fffc0f1194e7adbb93	2021-10-12	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

7428

Pubchem Substance ID

Not Available

ChEBI ID

551062

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BFL35-I:BFL36-J

EAFUS ID

Not Available

Dr. Duke ID

METHYL-GALLATE

BIGG ID

Not Available

KNApSAcK ID

C00030754

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

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
anti allergenic	50857	A drug used to treat allergic reactions.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti bronchitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	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 septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
Gram(+)icide	33282	A substance that kills or slows the growth of bacteria.	DUKE
Gram(-)icide	33282	A substance that kills or slows the growth of bacteria.	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
reverse transcriptase inhibitor	59897	An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the activity of reverse transcriptase, EC 2.7.7.49, a viral DNA polymerase enzyme that retroviruses need to reproduce.	DUKE
xanthine oxidase inhibitor	35634	An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).	DUKE