G6657

(−)-Gallocatechin

≥98% (HPLC)

• Synonym(s): (2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
• Empirical Formula (Hill Notation): C₁₅H₁₄O₇
• CAS Number: 3371-27-5
• Molecular Weight: 306.27
• MDL number: MFCD01632616
• UNSPSC Code: 12352205
• PubChem Substance ID: 24895266
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• solubility: H₂O: 5 mg/mL (heat 2-10 min at 105C); alcohol: soluble
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• SMILES string: O[C@@H]1Cc2c(O)cc(O)cc2O[C@H]1c3cc(O)c(O)c(O)c3
• InChI: 1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m1/s1
• InChI key: XMOCLSLCDHWDHP-DOMZBBRYSA-N

Description

General description

(−)-Gallocatechin is a polyphenolic compound and one of the primary catechins present in green tea Camellia sinensis.

Application

(−)-Gallocatechin has been used as a reference standard:

• for the identification of phenolic compounds present in Pineapple (Ananas comosus) using high-performance liquid chromatography (HPLC)
• to evaluate the catechin profiles from Camellia sinensis green tea, white tea, and flower sample by high-performance liquid chromatography/photodiode array detection (RP-HPLC/PDAD) analysis
• as a reference standard for the flavan-3-ols profiling muscadine grape hybrid varieties using high-performance liquid chromatography-quadrupole, time-of-flight, tandem mass spectrometry (HPLC-qTOF-MS/MS) analysis

Biochem/physiol Actions

(−)-Gallocatechin (GC) exerts antioxidant properties by scavenging free radicals. It can also inhibit osteoclastgenesis. GC elicits antimutagenic activity in Escherichia coli against ultraviolet (UV)-induced mutation. It also displays an inhibitory effect on the growth and adherence of Porphyromonas gingivalis in the buccal epithelial cells.

Other Notes

Polyphenolic compound found in green tea. An epimer of (−)-epigallocatechin.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: 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 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