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Compound Summary

General Compound Information

epigallocatechin-3-gallat

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Description

(-)-epigallocatechin 3-gallate is a gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin. It has a role as an antineoplastic agent, an antioxidant, a Hsp90 inhibitor, a neuroprotective agent and a plant metabolite. It is a gallate ester, a polyphenol and a member of flavans. It derives from a (-)-epigallocatechin.

Synonyms

(-)-Epigallocatechin gallate; EGCG; 989-51-5; Epigallocatechin gallate; Epigallocatechin 3-gallate;

Tea catechin;Epigallocatechin-3-gallate;(-)-Epigallocatechin-3-o-gallate;Teavigo;Epigallocatechin-3-monogallate;(-)-epigallocatechin 3-gallate;(-)-Epigallocatechol gallate;(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate;Catechin deriv.;PF-EGCg 90;NVP-XAA 723;BQM438CTEL;(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate;CHEBI:4806;CHEMBL297453;[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate;DTXSID1029889;[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate;(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate;Benzoic acid, 3,4,5-trihydroxy-, (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester;DTXCID80567;CAS-989-51-5;SMR000449288;CCRIS 3729;SR-01000759328;UNII-BQM438CTEL;L-Epigallocatechin gallate;Epigallocate;EPIGALOCATECHIN GALLATE;(-)-EGCG;Epigallocic acid;Teatannin II;2kdh;3oob;4awm;(-)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate;(-)-epigallocatechin 3-O-gallate;KDH;Epigallocatechol, 3-gallate, (-)-;Epigallocatechingallate;Epigallocatcchin Gallate;Epigallocatechin-gallate;Epigallocatechol Gallate;Spectrum_000316;SpecPlus_000277;Spectrum2_000168;Spectrum3_000244;Spectrum4_001541;Spectrum5_000102;Galloyl-L-epigallocatechol;EGCG [WHO-DD];EGCG [MI];3-O-Galloylepigallocatechin;(-)-Epigallocatechin gallat;(-)-Epigallocatehin gallate;SCHEMBL35258;BSPBio_001628;epigallocatechin-gallate-(-);KBioGR_002002;KBioSS_000796;SPECTRUM210239;cid_65064;MLS000758300;MLS001424000;DivK1c_006373;SPBio_000035;Epigallocatechin monogallate, B;GTPL7002;MEGxp0_001166;ACon1_001054;KBio1_001317;KBio2_000796;KBio2_003364;KBio2_005932;KBio3_001128;(-)-cis-3,3',4',5,5',7-Hexahydroxy-flavane-3-gallate;HMS2051K21;HMS3649E08;3-O-Galloyl-(-)-epigallocatechin;ZINC3870412;EPIGALLOCATECHIN 3-O-GALLATE;Tox21_201468;Tox21_303457;BDBM50070942;CCG-38378;FR-109;LMPK12030005;s2250;AKOS015918182;CS-1258;DB12116;DS-9030;EPIGALLOCATECHIN GALLATE [INCI];NC00078;SDCCGMLS-0066550.P001;(-)-Epigallocatechin gallate, >=95%;(-)-Epigallocatechin-3-gallate; EGCG;NCGC00164319-01;NCGC00164319-02;NCGC00164319-03;NCGC00164319-04;NCGC00164319-06;NCGC00257243-01;NCGC00259019-01;(-)-Epigallocatechin gallate (85% (-)-epigallocatechin gallate, 10% (-)-epigallocatechin, 5% (-)- epicatechin gallate);AC-34075;BP-30205;HY-13653;E0694;SW197458-3;C09731;M01719;(-)-Epigallocatechin gallate, >=97.0% (HPLC);(-)-Epigallocatechin gallate, analytical standard;A845931;Gallic acid, 3-ester with epigallocatechol, (-)-;Q393339;SR-01000946601;(-)-EPIGALLOCATECHIN-3-O-GALLATE [USP-RS];Q-100914;SR-01000759328-5;SR-01000759328-6;SR-01000946601-1;Epigallocatechin-3-gallate 1000 microg/mL in Acetonitrile;(-)-Epigallocatechin gallate, >=80% (HPLC), from green tea;Epigallocatechin gallate, primary pharmaceutical reference standard;(-)-Epigallocatechin-3-O-gallate, United States Pharmacopeia (USP) Reference Standard;(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl3,4,5-trihydroxybenzoate;[5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 2,3,4-trihydroxybenzoate;Epigallocatechin gallate, Pharmaceutical Secondary Standard; Certified Reference Material;(-)-cis-3,4-Dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1(2H)-benzopyran-3-yl Gallate;(-)-EPIGALLOCATECHIN GALLATE (85% (-)-EPIGALLOCATECHIN GALLATE, 10% (-)-EPIGALLOCATECHIN, 5% (-)-EPICATECHIN GALLATE);(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl-3,4,5-trihydroxybenzoate;[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl]3,4,5-trihydroxybenzoate;3,4,5-Trihydroxybenzoic acid (2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester;3,4-Dihydro-5,7-dihydroxy-2R-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3R-yl-3,4,5-trihydroxybenzoate;Benzoic acid, 3,4,5-trihydroxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester, (2R-cis)-;Benzoic acid, 3,4,5-trihydroxy-,(2R,3R)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3-yl ester;

FlavorDB ID

871 PUBCHEM ID

Molecular Weight

458.4 Molecular Formula

C22H18O11

Openeye Can Smiles

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

IUPAC Inchikey

WMBWREPUVVBILR-WIYYLYMNSA-N

Network

Similarity

CATEGORY	QUALITY	THRESHOLD	OCCURENCE	REFERENCE
taste	astringent	1.900e+2 µmol/L	cocoa	details
taste	astringent	1.900e+2 µmol/L	black tea	details
taste	bitter	1.900e+2 µmol/L	whisky	details
taste	astringent	1.900e+2 µmol/L	whisky	details

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database

EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Epigallocatechin-3-gallate

Reference point : Defined point on an experimental dose–response relationship for the critical effect. This term is synonymous to Point of departure (USA). Reference points include the lowest or no observed adverse effect level (LOAEL/NOAEL) or benchmark dose lower confidence limit (BDML), used to derive a reference value or Margin of Exposure in human and animal health risk assessment. In the ecological area, these include lethal dose (LD50), effect concentration (EC5/ECx), no (adverse) effect concentration/dose (NOEC/NOAEC/NOAED), no (adverse) effect level (NEL/NOAEL), hazard concentration (HC5/HCx) derived from a Species Sensitivity Distributions (SSD) for the ecosystem (EFSA Scientific Committee,2018). Citation: DOI 10.5281/zenodo.4740174

Reference point information of this compound is not available!

Reference Value

Reference Value : The estimated maximum dose (on a body mass basis) or the concentration of an agent to which an individual may be exposed over a specified period without appreciable risk. Reference values are established by applying an uncertainty factor to the reference point. Examples of reference values in human health include acceptable daily intake (ADI) for food and feed additives, and pesticides, tolerable upper intake levels (UL) for vitamins and minerals, and tolerable daily intake (TDI) for contaminants and food contact materials. For acute effects and operators, the acute reference dose (ARfD) and the acceptable operator exposure level (AOEL). In animal health and the ecological area, these include safe feed concentrations and the Predicted no effect concentration (PNEC) respectively (EFSA Scientific Committee, 2018). Citation: DOI 10.5281/zenodo.4740174

Reference value information of this compound is not available!

Genotoxicity

Author	YEAR	OUTPUT ID	Genotoxicity
EFSA ANS	2018	3050	No data

EFSA Outputs

Output ID	Title	DOI	Published
3050	Scientific opinion on the safety of green tea catechins	doi:10.2903/j.efsa.2018.5239	18Apr2018

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R4	details	Activated	100.00
TAS2R5	details	12.30 ± 3.63	100.00
TAS2R14	details	Activated	250.00
TAS2R30	details	Activated	100.00
TAS2R39	details	161.00; 8.50 ± 2.84	32.00; 100.00
TAS2R43	details	16.72	100.00

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental GCMS	view	GCMS	positive
Experimental LCMS	view	LCMS_Positive	positive
Experimental LCMS	view	LCMS_Negative	negative

Content

Compound Summary

epigallocatechin-3-gallat

Description

Synonyms

(-)-Epigallocatechin gallate; EGCG; 989-51-5; Epigallocatechin gallate; Epigallocatechin 3-gallate;

FlavorDB ID

871

PUBCHEM ID

65064

Molecular Weight

458.4

Molecular Formula

C22H18O11

Openeye Can Smiles

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

IUPAC Inchikey

WMBWREPUVVBILR-WIYYLYMNSA-N

Network

Shown in network

Similarity

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Content

Compound Summary

epigallocatechin-3-gallat

Description

Synonyms

(-)-Epigallocatechin gallate; EGCG; 989-51-5; Epigallocatechin gallate; Epigallocatechin 3-gallate;

FlavorDB ID

871

PUBCHEM ID

65064

Molecular Weight

458.4

Molecular Formula

C22H18O11

Openeye Can Smiles

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

IUPAC Inchikey

WMBWREPUVVBILR-WIYYLYMNSA-N

Network

Shown in network

Similarity

Show/Hide similarity panel

Reference Details

Reference Details

Reference Details

Reference Details

OpenFoodTox: component Epigallocatechin-3-gallate

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

Reference Details

GC-MS Spectrum

GC-MS Spectrum

GC-MS Spectrum