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Merck

G6657

Sigma-Aldrich

(−)-Gallocatechin

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C15H14O7
Número de CAS:
Peso molecular:
306.27
Número MDL:
Código UNSPSC:
12352205
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

Ensayo

≥98% (HPLC)

solubilidad

H2O: 5 mg/mL (heat 2-10 min at 105C)
alcohol: soluble

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

temp. de almacenamiento

2-8°C

cadena SMILES

O[C@@H]1Cc2c(O)cc(O)cc2O[C@H]1c3cc(O)c(O)c(O)c3

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

Clave InChI

XMOCLSLCDHWDHP-DOMZBBRYSA-N

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Descripción general

(−)-Gallocatechin is a polyphenolic compound and one of the primary catechins present in green tea Camellia sinensis.

Aplicación

(−)-Gallocatechin has been used as a reference standard:
  • for the identification of phenolic compounds present in Pineapple (Ananas comosus) using high-performance liquid chromatography (HPLC)
  • to evaluate the catechin profiles from Camellia sinensis green tea, white tea, and flower sample by high-performance liquid chromatography/photodiode array detection (RP-HPLC/PDAD) analysis
  • as a reference standard for the flavan-3-ols profiling muscadine grape hybrid varieties using high-performance liquid chromatography-quadrupole, time-of-flight, tandem mass spectrometry (HPLC-qTOF-MS/MS) analysis

Acciones bioquímicas o fisiológicas

(−)-Gallocatechin (GC) exerts antioxidant properties by scavenging free radicals. It can also inhibit osteoclastgenesis. GC elicits antimutagenic activity in Escherichia coli against ultraviolet (UV)-induced mutation. It also displays an inhibitory effect on the growth and adherence of Porphyromonas gingivalis in the buccal epithelial cells.

Otras notas

Polyphenolic compound found in green tea. An epimer of (−)-epigallocatechin.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Chun Hay Ko et al.
Journal of agricultural and food chemistry, 57(16), 7293-7297 (2009-08-06)
In this study, three tea catechins, epigallocatechin (EGC), gallocatechin (GC), and gallocatechin gallate (GCG), were investigated for their effects on bone metabolism. The effects of the tea catechins on bone formation were evaluated using cultured rat osteoblast-like osteosarcoma cell line
Simultaneous analysis of individual catechins and caffeine in green tea
Goto T, et al.,
Journal of Chromatography A, 295-299 (1996)
Q Guo et al.
Biochimica et biophysica acta, 1427(1), 13-23 (1999-03-20)
The purpose of this study is to examine the relationship between the free radical scavenging activities and the chemical structures of tea catechins ((-)-epigallocatechin gallate (EGCG), (-)-epigallocatechin (EGC) and (-)-epicatechin (EC)) and their corresponding epimers ((-)-gallocatechin gallate (GCG), (-)-gallocatechin (GC)
G W Plumb et al.
Redox report : communications in free radical research, 7(1), 41-46 (2002-05-01)
Gallocatechins and a range of prodelphinidins were purified by high performance liquid chromatography from pomegranate peel. Gallocatechin, gallocatechin-(4-8)-catechin, gallocatechin-(4-8)-gallocatechin and catechin-(4-8)-gallocatechin were all identified, purified and quantified by LC-DAD-MS and MS-MS. The antioxidant properties of these compounds were assessed using
In vitro gastrointestinal digestion and colonic fermentation of phenolic compounds in UV-C irradiated pineapple (Ananas comosus) snack-bars
Del juncal-Guzman D, et al.,
LWT--Food Science and Technology, 110636-110636 (2021)

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