Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2019-11-26 02:55:10 UTC
Primary IDFDB000663
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyl gallate
DescriptionMethyl 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 Number99-24-1
Structure
Thumb
Synonyms
SynonymSource
Methyl gallic acidGenerator
Methyl 3ChEMBL
45-TrihydroxybenzoateChEMBL
Methyl galloateChEMBL
345-Trihydroxy-benzoic acid methyl esterChEMBL
45-Trihydroxybenzoic acidGenerator
Methyl galloic acidGenerator
345-Trihydroxy-benzoate methyl esterGenerator
Gallic acid, methyl esterMeSH
Methyl 3,4,5-trihydroxybenzoateMeSH
3,4,5-Trihydroxy-benzoic acid methyl esterbiospider
Benzoic acid, 3,4,5-trihydroxy-, methyl esterbiospider
Gallic acid methyl esterbiospider
Gallicin?db_source
Methyl gallatedb_source
Methylgallatebiospider
Predicted Properties
PropertyValueSource
Water Solubility4.11 g/LALOGPS
logP1.01ALOGPS
logP1.07ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.11ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.03 m³·mol⁻¹ChemAxon
Polarizability16.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O5
IUPAC namemethyl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3
InChI KeyFBSFWRHWHYMIOG-UHFFFAOYSA-N
Isomeric SMILESCOC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight184.1461
Monoisotopic Molecular Weight184.037173366
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentGalloyl 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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.18%; H 4.38%; O 43.44%DFC
Melting PointMp 157°DFC
Boiling PointNot Available
Experimental Water Solubility10.6 mg/mLYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.86HANSCH,C ET AL. (1995)
Experimental pKapKa1 7.88 (25°, 0.1M KNO3)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data283 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMethyl gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ufr-0900000000-72baa95f31204513dc9dSpectrum
Predicted GC-MSMethyl gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl gallate, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-9700000000-11744c62170a98354cbc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-1900000000-d6261b21dc9a9fd566b92021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-401d71dbf57a34ddc2352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-51202d68563eee1bdab22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvj-5900000000-b7c5629192d45e0d9cb12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-90389cc7f792df061dc32016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-50a11e1df989b937ae232016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-5900000000-59e6084d7e7bb182a1a72016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-fc79f14d18e4e34433ab2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fc0-1900000000-16bd999e2e402d7a09122021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067l-9300000000-e54d0ca66a63d30da4f12021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-366cfe98e3457a4b68f32021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-1900000000-5526e088c3d9034b92352021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gds-9300000000-b3fffc0f1194e7adbb932021-10-12View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID7428
Pubchem Substance IDNot Available
ChEBI ID551062
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFL35-I:BFL36-J
EAFUS IDNot Available
Dr. Duke IDMETHYL-GALLATE
BIGG IDNot Available
KNApSAcK IDC00030754
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-allergenic50857 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-asthmatic49167 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 bacterial33282 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-bronchitic52217 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-herpetic22587 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 leukemic35610 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-oxidant22586 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 septic33281 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-staphylococcic33282 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
Antitumor35610 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-viral22587 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(+)icide33282 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(-)icide33282 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
Pesticide25944 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 inhibitor59897 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 inhibitor35634 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.