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C0692

Sigma-Aldrich

(−)-Catechin gallate

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

biological source

green tea

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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
Urška Jug et al.
Journal of chromatography. A, 1637, 461802-461802 (2021-01-01)
A methodology based on off-line multidimensional thin-layer chromatography was developed for isolation of several secondary metabolites from bark of Japanese knotweed (Fallopia japonica Houtt.) rhizomes. Successive fractionation steps using PLC silica gel and HPTLC silica gel or HPTLC cellulose plates
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
Fan Jiang et al.
Clinical immunology (Orlando, Fla.), 137(3), 347-356 (2010-09-14)
Four catechins with the galloyl moiety, including catechin gallate (CG), epigallocatechin gallate (EGCG), gallocatechin gallate (GCG), and epicatechin gallate (ECG), were found to inhibit HIV-1 integrase effectively as determined by our ELISA method. In our docking study, it is proposed
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
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