Basic information
- CAS
1617-55-6- Standard SMILES
Oc1cc(O)c2c(c1)O[C@H](c1cc(O)c(O)c(O)c1)[C@@H](O)C2- InChIKey
XMOCLSLCDHWDHP-SWLSCSKDSA-N- Molecular formula
- C15H14O7
- Average molar mass
- 306.27 g/mol
- Monoisotopic mass
- 306.07395278
Overview
Gallocatechin is a catechin that is a flavan substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7 (the trans isomer). It is isolated from Acacia mearnsii. It has a role as a metabolite. It is a catechin and a flavan-3,3',4',5,5',7-hexol.
Names & identifiers
- Preferred name
- Gallocatechin
- IUPAC
- (2R,3S)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
- English name
- (+)-GALLOCATECHIN
- Molecular formula
- C15H14O7
- Molecular weight
- 306.27
Names & synonyms
(+)-GallocatechinGallocatechin970-73-0Gallocatechol(+)-gallocatechol(2R,3S)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triolHEJ6575V1X(2R,3S)-gallocatechinNSC-674038CHEBI:31018CHEBI:68330DTXSID10914220
Show more names
Nsc674038(+)-Gallocatechin GC(+)-Gallocatechin Standard(+)-Gallocatechin, 10 mM in DMSO(2R,3S)-2-(3,4,5-trihydroxyphenyl)chroman-3,5,7-triol2α-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3β,5,7-triol(2S)-3,4-Dihydro-2β-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3α,5,7-triol
2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-, (2R,3S)-RefChem:5850DTXCID2013432151617-55-6d-GallocatechinGallocatechol, (+-)-(2R,3S)-2-(3,4,5-trihydroxyphenyl)chromane-3,5,7-triolMFCD06798946
Database identifiers
- CAS
1617-55-6、970-73-0
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 131 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 380
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavans, Flavanols and Leucoanthocyanidins [PK1202]
SpringerMaterials PropertiesCrystal structure
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point189 - 191 °C
Physical DescriptionSolid
Physicochemical properties
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly, Sonicated), Ethanol (Slightly, Sonicated), Methanol (Slightly)
- Boiling point
- 685.6 · 685.6±55.0 °C(Predicted)
- Density
- 1.695 · 1.695±0.06 g/cm3(Predicted)
- Melting point
- 218 °C · 218 °C(Solv: water (7732-18-5))
- pka
- 9.02 · 9.02±0.15(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312-P330-P302+P352-P321-P304+P340-P305+P351+P338-P332+P313-P362+P364-P337+P313-P403+P233-P405-P501
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
Description(+)-Gallocatechin is a polyphenol and flavonoid that has been isolated from the leaves of tea plants and has diverse biological activities. It inhibits the adherence of P. gingivalis onto human buccal epithelial cells by more than 50% when used at a concentration of 250 μg/ml. (+)-Gallocatechin has antimutagenic properties in UV-irradiated E. coli cells. It inhibits cell death induced by D-galactosamine and TNF-α in primary cultured mouse hepatocytes by 29.9% when used at a concentration of 80 μM. (+)-Gallocatechin (100 μM) inhibits HCT116 colorectal cancer cell proliferation by 57%.
Uses(+)-Gallocatechin is antioxidant isomer of (-)-Gallocatechin (G188990), a potential cancer chemopreventive agent that inhibits the growth and adherence of P. gingivalis onto the buccal epithelial cells. An epimer of (-)-Epigallocatechin (E588940).
Suppliers6 total
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
四川恒诚致远生物科技有限公司18113192475 18113192475 · [email protected]
青岛浩海安杰医药科技有限公司156-6622-8711 18639325623 · [email protected]
Alchem Pharmtech,Inc.8485655694 · [email protected]
上海甄准生物科技有限公司18019219489 18901678489 · [email protected]
南京世洲生物科技有限公司17301488900 · [email protected]
Related reactions
0 records
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Compound notes
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