Milk Composition Database: Showing metabocard for gallic acid (BMDB0063600)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-10-03 16:32:23 UTC

Update Date

2020-06-04 19:00:34 UTC

MCDB ID

BMDB0063600

Secondary Accession Numbers

BMDB63600

Metabolite Identification

Common Name

gallic acid

Description

Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid has the chemical formula is C6H2(OH)3CO2H. It is commonly used in the pharmaceutical industry. Gallic acid can also be used to synthesize the hallucinogenic alkaloid mescaline, also known as 3,4,5-trimethoxyphenethylamine. Salts and esters of gallic acid are termed gallates (Wikipedia).

Structure

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

Synonyms

Value	Source
3,4,5-Trihydroxybenzoic acid	ChEBI
Pyrogallol-5-carboxylic acid	ChEBI
3,4,5-Trihydroxybenzoate	Kegg
Pyrogallol-5-carboxylate	Generator
Gallate	Generator
Acid, gallic	MeSH
3,4,5-Trihydroxy-benzoate	HMDB
3,4,5-Trihydroxy-benzoic acid	HMDB
3,4,5-Trihydroxybenzoic acid (acd/name 4.0)	HMDB
Gallic acid polymer	HMDB
Gallic acid tech.	HMDB
Galop	HMDB
3,4,5-Hydroxybenzoic acid	PhytoBank
Gallic acid	HMDB

Chemical Formula

C₇H₆O₅

Average Molecular Weight

170.12

Monoisotopic Molecular Weight

170.021523293

IUPAC Name

3,4,5-trihydroxybenzoic acid

Traditional Name

galop

CAS Registry Number

149-91-7

SMILES

OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)

InChI Key

LNTHITQWFMADLM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gallic acids. These are organic compounds that contain 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 acids

Alternative Parents

Substituents

Gallic acid
Benzenetriol
Benzoic acid
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

trihydroxybenzoic acid (CHEBI:30778 )
Gallotannins (C01424 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	258 - 265 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.9 mg/mL at 20 °C	Not Available
LogP	0.7	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.17	ALOGPS
logP	0.72	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.26 m³·mol⁻¹	ChemAxon
Polarizability	14.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001i-0791200000-4d3e1baed2effb0bf15b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-053r-0491700000-68a1d17dd1d0bb6c5354	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fk9-5900000000-6b43adb858d50b520ba7	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-0791200000-4d3e1baed2effb0bf15b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-053r-0491700000-68a1d17dd1d0bb6c5354	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-0691200000-8b11cbd28f656c4426b4	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fmi-1900000000-56bf9b5e0a68a9c0776a	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-00xu-4009300000-4326897e134d4856b180	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0umi-0900000000-e8e6e57cdaf8d518781a	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-9600000000-8b3c3dc9e263c174a0ac	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ue9-9000000000-da4704e31ba4de6b3aca	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0fk9-5900000000-425a258abda96a507ea0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-951aa8106825faaca3f9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-bdedf4b4b4fd922ec704	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-5900000000-46d7a232b169910da462	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9300000000-010429242e38b1b28c13	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0g29-9100000000-fb4dc241b26c248950f7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0ufr-0900000000-8e1ce790677a7c04e580	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-004i-0900000000-8999270f1e2b746047f7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-880097b21bcd57ec8f77	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-bdedf4b4b4fd922ec704	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-5900000000-bf4cb2a480d9abb570d4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9300000000-63bfcc112fc600a150de	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0g29-9100000000-fb4dc241b26c248950f7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-6a9289e729e66d03cf50	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-175241488c5f0956df1f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0kor-0900000000-1ceb76e12bc399878e0d	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-8e403dcee60bc20ba7b4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fb9-0900000000-20a78444c2179ed7730f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00os-9800000000-3011ae50626d9c15fadd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-bceef5d1a34c38d340ed	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00or-0900000000-bbec391317d064ab4d89	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-8900000000-049b564c5923498a6f3e	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fk9-2900000000-1949ca7ce1b8b610c278	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)	Not Available	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Not Available	2015-03-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.00411 +/- 0.00024 uM	Shin Tsen, Jinyi ...	details
Detected and Quantified	0.002 +/- 0.0011 uM	Shin Tsen, Jinyi ...	details
Detected and Quantified	0.000235 +/- 0.000235 uM	Shin Tsen, Jinyi ...	details
Detected and Quantified	0.00411 +/- 0.00035 uM	Shin Tsen, Jinyi ...	details

External Links

HMDB ID

HMDB0005807

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Gallic_acid

METLIN ID

3295

PubChem Compound

370

PDB ID

Not Available

ChEBI ID

30778

References

Synthesis Reference

Cheng K F; Yip C S; Yeung H W; Kong Y C Leonurine, an improved synthesis. Experientia (1979), 35(5), 571-2. PubMed ID 446644

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke (2014). Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke Cow’s milk as a dietary source of equol and phenolic antioxidants: di erential distribution in the milk aqueous and lipid fractions. Dairy Sci. & Technol. (2014) 94:625–632. DOI 10.1007/s13594-014-0183-4. Dairy Science & Technology.

Showing metabocard for gallic acid (BMDB0063600)

Structure for BMDB0063600 (gallic acid)