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C0692

Sigma-Aldrich

(−)-Catechin gallate

≥98% (HPLC), from green tea

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C22H18O10
Número de CAS:
130405-40-2
Peso molecular:
442.37
Número MDL:
MFCD00214258
Código UNSPSC:
12352205
ID de la sustancia en PubChem:
57653978
NACRES:
NA.77

origen biológico

green tea

Ensayo

≥98% (HPLC)

Formulario

powder

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

temp. de almacenamiento

2-8°C

cadena SMILES

Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@@H](Oc2c1)c4ccc(O)c(O)c4

InChI

1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21+/m1/s1

Clave InChI

LSHVYAFMTMFKBA-CTNGQTDRSA-N

Información sobre el gen

human ... BACE1(23621)

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Descripción general

(−)-Catechin gallate belongs to a class of polyphenol compounds that are formed when catechins in green tea undergo epimerization on heat treatment. It is a naturally occurring flavanol catechin having a galloyl moiety.

Aplicación

(−)-Catechin gallate has been used:
  • to examine the potency of catechins containing galloyl moiety in inhibiting the activity of human immunodeficiency virus-1 (HIV-1)integrase
  • to analyze the anti-oxidant and anti-viral properties of Pseudopiptadenia contorta and the commercial quebracho extracts in a herpes simplex virus type 1 strain, resistant to acyclovir
  • to study the effects of polyphenols on the biochemistry of human spermatozoa and the associated limitations of their use in gamete preservation

Acciones bioquímicas o fisiológicas

(−)-Catechin gallate inhibits the absorption of glucose in adipocytes isolated from rats. It is also reported to exhibit anti-oxidative properties along with a capacity to decrease plasma cholesterol levels. (−)-Catechin gallate shows the potency to be used as an agent to modify antibiotic resistance.
Antioxidant constituent of green tea.
Antioxidant constituent of green tea. At μM concentrations, it inhibits VEGF-induced tyrosine phosphorylation. It also inhibits aromatase activity, an enzyme that converts androgens to estrogen and is thought to play a role in the etiology of breast cancer.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H315,H319,H335

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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Certificados de análisis (COA)

Lot/Batch Number
0000426199
0000426199
0000340213
0000340212
0000340213

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Pablo Strobel et al.
The Biochemical journal, 386(Pt 3), 471-478 (2004-10-08)
The facilitative glucose transporter, GLUT4, mediates insulin-stimulated glucose uptake in adipocytes and muscles, and the participation of GLUT4 in the pathogenesis of various clinical conditions associated with obesity, visceral fat accumulation and insulin resistance has been proposed. Glucose uptake by
Meng Shi et al.
Food research international (Ottawa, Ont.), 132, 109050-109050 (2020-04-26)
Matcha-tuna oil and matcha-maltodextrin-tuna oil emulsions (25% oil, dry basis), formulated to have protein: carbohydrate ratios of 1:1.1, 1:2, 1:3 and 1:4, were spray dried. Confocal laser scanning microscopy showed effective emulsification of oil in all emulsions. All powders had
Antioxidant and antiviral properties of Pseudopiptadenia contorta (Leguminosae) and of quebracho (Schinopsis sp.) extracts
Moreira DL, et al.
Quimica nova, 28(3), 421-425 (2005)
Paul D Stapleton et al.
Antimicrobial agents and chemotherapy, 50(2), 752-755 (2006-01-27)
(-)-Epicatechin gallate (ECg) and (-)-epigallocatechin gallate (EGCg) reduce oxacillin resistance in mecA-containing strains of Staphylococcus aureus. Their binding to staphylococcal cells is enhanced by the nongalloyl analogues (-)-epicatechin (EC) and (-)-epigallocatechin (EGC). EC and EGC significantly increased the capacity of
Chuang Zhang et al.
Food chemistry, 244, 109-119 (2017-11-10)
Tea polyphenols have been a topic of discussion due to their health benefits. Nevertheless, detailed studies on the antioxidant capacity and polyphenol contents of teas in relation to factors including geographical locations, plantation elevations and leaf grades have been limited.
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