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

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	An agent that reduces or blocks allergic reactions, commonly used to treat conditions such as hay fever, asthma, and skin allergies, by inhibiting the release of histamine and other inflammatory mediators, providing relief from symptoms like itching, sneezing, and congestion.	DUKE
Anti-asthmatic	49167	An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti-bronchitic	52217	An agent that relieves bronchial congestion and inflammation, commonly used in managing respiratory disorders such as bronchitis, asthma, and chronic obstructive pulmonary disease (COPD), to reduce coughing, wheezing, and shortness of breath.	DUKE
Anti-herpetic	22587	An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.	DUKE
Anti leukemic	35610	An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-staphylococcic	33282	An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Gram(+)icide	33282	An agent that targets and kills Gram-positive bacteria, playing a crucial role in treating bacterial infections. Therapeutically, it is used to combat infections caused by Gram-positive microorganisms, with key medical applications including treating skin infections, pneumonia, and sepsis.	DUKE
Gram(-)icide	33282	An agent that kills Gram-negative bacteria, playing a crucial role in treating infections. Therapeutically, it is used to combat bacterial infections, particularly those resistant to other antibiotics. Key medical uses include treating sepsis, pneumonia, and urinary tract infections caused by Gram-negative bacteria.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Reverse transcriptase inhibitor	59897	An agent that blocks the activity of reverse transcriptase, an enzyme used by retroviruses to replicate. Therapeutically, it prevents viral replication, commonly used in managing HIV/AIDS and other retroviral infections, such as hepatitis B.	DUKE
Xanthine oxidase inhibitor	35634	An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.	DUKE