AFCDB: Epigallocatechin (FDB017700)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:15 UTC

Update date

2019-11-26 03:15:04 UTC

Primary ID

FDB017700

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Epigallocatechin

Description

(-)-Epigallocatechin, also known as epigallocatechol, belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety (-)-Epigallocatechin is a bitter tasting compound (-)-Epigallocatechin is found, on average, in the highest concentration within a few different foods, such as cocoa beans (Theobroma cacao), green tea, and black tea and in a lower concentration in herbal tea, peanuts (Arachis hypogaea), and pomegranates (Punica granatum) (-)-Epigallocatechin has also been detected, but not quantified in, several different foods, such as common beets (Beta vulgaris), pine nuts (Pinus), common mushrooms (Agaricus bisporus), red bell peppers (Capsicum annuum), and allia (Allium). This could make (-)-epigallocatechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (-)-Epigallocatechin.

CAS Number

970-74-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.87 g/L	ALOGPS
logP	0.71	ALOGPS
logP	1.49	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	130.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.98 m³·mol⁻¹	ChemAxon
Polarizability	29.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H14O7

IUPAC name

(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

InChI Identifier

InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1

InChI Key

XMOCLSLCDHWDHP-IUODEOHRSA-N

Isomeric SMILES

O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C2O

Average Molecular Weight

306.2675

Monoisotopic Molecular Weight

306.073952802

Classification

Description

Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Epigallocatechins

Alternative Parents

Substituents

Epigallocatechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
Pyrogallol derivative
Benzenetriol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:42255 )
flavan-3,3',4',5,5',7-hexol (CHEBI:42255 )
Flavans, Flavanols and Leucoanthocyanidins (C12136 )
Flavan 3-ols (C12136 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020004 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Antineoplastic agent:

Biological role:

Nutrient

Foods

Cocoa and cocoa products

Nuts and legumes:

Nuts

Fruits and vegetables:

Fruits:

Berries

Pomes:

Apple

Red wine

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

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 58.83%; H 4.61%; O 36.57%	DFC
Melting Point	Mp 219-221° dec.	DFC
Optical Rotation	[a]D -60.3 (c, 0.3 in EtOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Epigallocatechin, non-derivatized, GC-MS Spectrum	splash10-0a4i-0978700000-567c7251027c80e91a01	Spectrum
GC-MS	Epigallocatechin, non-derivatized, GC-MS Spectrum	splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6	Spectrum
GC-MS	Epigallocatechin, non-derivatized, GC-MS Spectrum	splash10-0a4i-0978700000-567c7251027c80e91a01	Spectrum
GC-MS	Epigallocatechin, non-derivatized, GC-MS Spectrum	splash10-0a4i-0967700000-febb7658ba2d5bd6d9b6	Spectrum
Predicted GC-MS	Epigallocatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-0940000000-a9630fe8d1a042f59c2a	Spectrum
Predicted GC-MS	Epigallocatechin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udi-3110049000-8b1040defcae8063c769	Spectrum
Predicted GC-MS	Epigallocatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pb9-0019003000-c4d2b02a82d1cf14714e	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0pb9-0019003000-c4d2b02a82d1cf14714e	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-002r-0910000000-8dfe0ba4e2ec1225213f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0pb9-0019003000-c4d2b02a82d1cf14714e	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-00p0-0951000000-95142c4b42b35c4bdac9	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-000i-0900000000-4e9ebbe814af2f8c284d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-05r0-0913000000-be7d3c4d9b40f51414e7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0529000000-0036b0386a7ade78fcac	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00vi-0690000000-702c5a1e065692895b3a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00vi-0690000000-7844ed1a917693a67b37	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0a4i-0029000000-82c2dfbbc69b748bc6f3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-002r-0910000000-8dfe0ba4e2ec1225213f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-00p0-0951000000-95142c4b42b35c4bdac9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-c79003b472daf421e492	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0910000000-f92cf1606a46a5b16f4f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0910000000-2026f33ac95d368b5268	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0729000000-fffbd456b9b51c7d0274	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0911000000-203a6a86214265bc09e4	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ds-2900000000-023b154fc2d731ecee10	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0219000000-db1826421845ecab1485	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05n0-0922000000-86fb5a0b2fc660815604	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-2910000000-2375ce05cd5da757763c	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

42255

Phenol-Explorer ID

127

DrugBank ID

Not Available

HMDB ID

HMDB38361

CRC / DFC (Dictionary of Food Compounds) ID

KZF28-J:KZF29-K

EAFUS ID

Not Available

Dr. Duke ID

EPIGALLOCATECHOL|(-)-EPI-GALLO-CATECHOL|(-)-EPIGALLOCATECHIN|EPIGALLOCATECHIN

BIGG ID

Not Available

KNApSAcK ID

C00008818

HET ID

EGT

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

127

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Show entries

Search:

Descriptor	ID	Definition	Reference
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
angiotensin converting enzyme inhibitor	35457	An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).	DUKE
anti acne	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti amebic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti carcinogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti caries	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti giardial			DUKE
anti mutagenic			DUKE
anti radicular			DUKE

Showing 1 to 10 of 20 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Show entries

Search:

Showing 1 to 1 of 1 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Epigallocatechin (FDB017700)

Structure for FDB017700 (Epigallocatechin)