C0692

(−)-Catechin gallate

Name: (−)-Catechin gallate
Brand: SIGMA

≥98% (HPLC), from green tea

Synonym(s):

(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

Empirical Formula (Hill Notation):

C₂₂H₁₈O₁₀

CAS Number:

130405-40-2

Molecular Weight:

442.37

NACRES:

NA.77

PubChem Substance ID:

57653978

UNSPSC Code:

12352205

MDL number:

MFCD00214258

Key Documents

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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)

Related Categories

Biochemicals

Natural Products for Research and Discovery

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.[1][2][3]

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[1]
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[2]

Biochem/physiol Actions

(−)-Catechin gallate inhibits the absorption of glucose in adipocytes isolated from rats.[3] It is also reported to exhibit anti-oxidative properties along with a capacity to decrease plasma cholesterol levels.[4] (−)-Catechin gallate shows the potency to be used as an agent to modify antibiotic resistance.[5]

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.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000491296

0000448624

0000473021

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Myricetin, quercetin and catechin-gallate inhibit glucose uptake in isolated rat adipocytes.

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

Oxidative stability of spray dried matcha-tuna oil powders.

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)

Heat-epimerized tea catechins rich in gallocatechin gallate and catechin gallate are more effective to inhibit cholesterol absorption than tea catechins rich in epigallocatechin gallate and epicatechin gallate.

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

Mass spectrometry-based systems approach for identification of inhibitors of Plasmodium falciparum fatty acid synthase.

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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Articles

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

Global Trade Item Number

SKU	GTIN
C0692-1MG	04061833451472
C0692-5MG	04061833451489

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