C0692

(−)-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: 130405-40-2
• Molecular Weight: 442.37
• NACRES: NA.77
• PubChem Substance ID: 57653978
• UNSPSC Code: 12352205
• MDL number: MFCD00214258

Properties

• 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
• 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 key: LSHVYAFMTMFKBA-CTNGQTDRSA-N
• biological source: green tea
• assay: ≥98% (HPLC)
• form: powder
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• Quality Level: 200
• Gene Information: human ... BACE1(23621)

Description

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[4]
• 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.[5] (−)-Catechin gallate shows the potency to be used as an agent to modify antibiotic resistance.[6]

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.

Safety Information

• 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