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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)
Empirical Formula (Hill Notation):
C22H18O10
CAS Number:
Molecular Weight:
442.37
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

green tea

assay

≥98% (HPLC)

form

powder

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

Packaging

1, 5 mg in glass bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C0692.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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