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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
MDL number:
MFCD00214258
UNSPSC Code:
12352205
PubChem Substance ID:
57653978
NACRES:
NA.77

biological source

green tea

Quality Level

200

assay

≥98% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

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

InChI key

LSHVYAFMTMFKBA-CTNGQTDRSA-N

Gene Information

human ... BACE1(23621)

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General description

(−)-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.

Application

(−)-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

Biochem/physiol Actions

(−)-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. 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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
Ikuo Ikeda et al.
Journal of agricultural and food chemistry, 51(25), 7303-7307 (2003-12-04)
It has been known that tea catechins, (-)-epicatechin (1), (-)-epigallocatechin (2), (-)-epicatechin gallate (3), and (-)-epigallocatechin gallate (4) are epimerized to(-)-catechin (5), (-)-gallocatechin (6), (-)-catechin gallate (7), and (-)-gallocatechin gallate (8), respectively, during retort pasteurization. We previously reported that tea
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.
Shilpi Sharma et al.
Antimicrobial agents and chemotherapy, 51(7), 2552-2558 (2007-05-09)
The emergence of strains of Plasmodium falciparum resistant to the commonly used antimalarials warrants the development of new antimalarial agents. The discovery of type II fatty acid synthase (FAS) in Plasmodium distinct from the FAS in its human host (type
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