4233-96-9

Basic information

• Product Name: (-)-Gallocatechin gallate
• Synonyms: (-)-gallocatecholgallate;(2s-trans)-henyl)-2h-1-benzopyran-3-yleste;benzoicacid,3,4,5-trihydroxy-,3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyp;[2S,3R]-2-[3,4,5-TRIHYDROXYPHENYL]-3,4-DIHYDRO-1[2H]-BENZOPYRAN-3,5,7-TRIOL 3-[3,4,5-TRIHYDROXYBENZOATE;(-)-GCG;(-)-GALLOCATECHIN GALLATE;GALLOCATECHIN GALLATE;GALLOCATECHIN GALLATE, (-)-
• CAS NO: 4233-96-9
• Molecular Formula: C₂₂H₁₈O₁₁
• Molecular Weight: 458.37
• EINECS: 2017-001-1
• Product Categories: Catechins & Tannins;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 4233-96-9.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 909.1 °C at 760 mmHg
• Flash Point: 320 °C
• Appearance: /
• Density: 1.9 g/cm³
• Vapor Pressure: 3.71E-35mmHg at 25°C
• Refractive Index: 1.857
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.75±0.25(Predicted)
• CAS DataBase Reference: (-)-Gallocatechin gallate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Gallocatechin gallate(4233-96-9)
• EPA Substance Registry System: (-)-Gallocatechin gallate(4233-96-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-26/36
• WGK Germany: 3
• RTECS: DH9000000
• Hazardous Substances Data: 4233-96-9(Hazardous Substances Data)

Usage

Description

(-)-Gallocatechin gallate, also known as GCG, is a naturally occurring polyphenolic compound belonging to the catechin class. It is predominantly found in green tea (Camellia sinensis) and is known for its potent antioxidant, anti-inflammatory, and anticancer properties. The molecular structure of GCG features a flavan-3-ol skeleton with a gallate ester group attached, which contributes to its unique biological activities.

Uses

Used in Pharmaceutical Industry:
(-)-Gallocatechin gallate is used as a therapeutic agent for its potential anticancer properties. It has been shown to inhibit the growth and proliferation of various cancer cell lines by targeting multiple signaling pathways involved in cell cycle regulation, apoptosis, and angiogenesis. Additionally, GCG exhibits synergistic effects when combined with conventional chemotherapeutic drugs, enhancing their efficacy and overcoming drug resistance in cancer treatment.
Used in Nutraceutical Industry:
(-)-Gallocatechin gallate is used as a key ingredient in dietary supplements and functional foods due to its antioxidant and anti-inflammatory properties. It helps in reducing the risk of chronic diseases, such as cardiovascular diseases, diabetes, and neurodegenerative disorders, by neutralizing free radicals and modulating inflammatory responses.
Used in Cosmetic Industry:
(-)-Gallocatechin gallate is used as an active ingredient in skincare products for its anti-aging and skin protective effects. It helps in reducing the visible signs of aging, such as wrinkles and fine lines, by promoting collagen synthesis and inhibiting matrix metalloproteinases (MMPs). Furthermore, GCG protects the skin from environmental stressors, such as UV radiation and pollution, by enhancing the skin's antioxidant defense mechanisms.
Used in Food and Beverage Industry:
(-)-Gallocatechin gallate is used as a natural preservative and antioxidant in the food and beverage industry. It helps in extending the shelf life of perishable products by preventing lipid oxidation and rancidity. Additionally, GCG can be used as a flavor enhancer and color stabilizer in various food products, such as tea, chocolate, and confectionery items.
Used in Drug Delivery Systems:
(-)-Gallocatechin gallate is used as a component in the development of novel drug delivery systems, such as nanoparticles and liposomes, to improve the bioavailability and targeted delivery of therapeutic agents. Its antioxidant and anti-inflammatory properties can also be harnessed to design stimuli-responsive drug carriers that release their payload in response to specific biological cues, such as pH changes or the presence of specific enzymes.

InChI:InChI=1/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21+/m1/s1

Upstream product

• 225793-49-7 EGCg quinone dimer A 
• 86588-88-7 (2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin-3''-O-gallate 
• 2596-50-1 (-)-epigallocathechin gallate 
• 50-99-7 D-glucose 
• 3081-61-6 N-ethyl-L-glutamine 
• 528852-04-2 C₇₈H₆₆O₁₁ 
• 333796-77-3 (E)-1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-3-[3,4,5-tris(benzyloxy)phenyl]propenone 
• 333796-78-4 5,7-dibenzyloxy-2-[3,4,5-tris(benzyloxy)phenyl]-2H-chromene 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 896121-45-2 5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-ol 
• 108-73-6 3,5-dihydroxyphenol 
• 1359849-48-1 epigallocatechin-3-O-p-hydroxybenzoate-(4β->8)-epigallocatechin-3-O-gallate 
• 100-53-8 phenylmethanethiol 
• 108-98-5 thiophenol 

Downstream Products

• 569-77-7 purpurogallin 
• 102067-92-5 epitheaflagallin 3-O-gallate 
• 224434-07-5 (-)-(2R,3R)-5,7-bis(hydroxy)-2-(3,4,5-tris(hydroxy)phenyl)chroman-3-yl-(3,5-bisbenzyloxy-4-methoxy)benzoate 
• 148707-39-5 (-)-epigallocatechin 3-O-galloylperacetate 
• 225793-49-7 EGCg quinone dimer A 
• 30462-34-1 theaflavin-3-gallate 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 989-51-5 (-)-gallocatechin 3-gallate 

Relevant articles and documents

Study on in Vitro Preparation and Taste Properties of N-Ethyl-2-Pyrrolidinone-Substituted Flavan-3-Ols

N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs) were prepared by an in vitro model reaction, and the taste thresholds of EPSFs and their dose-over-threshold factors in large-leaf yellow tea (LYT) were investigated. The effects of initial reactant

Oligomerization mechanism of tea catechins during tea roasting

Roasting of green tea causes oligomerization of tea catechins, which decreases the astringency. The aim of this study was to elucidate the oligomerization mechanism. The 13C NMR spectrum of the oligomer fraction showed signals arising from catechin and sugar residues. Heating of epigallocatechin-3-O-gallate with 13C-labeled glucose (150 °C for 2 h) suggested that condensation of sugars with catechin A-rings caused the oligomerization. The dimeric product obtained by heating for a shorter period (30 min) suggested cross-linking occurred between sugars and catechin A-rings. Furthermore, heating of phloroglucinol, a catechin A-ring mimic, with glucose, methylglyoxal, and dihydroxyacetone, confirmed that the basic mechanism included reaction of the catechin A-ring methine carbons with carbonyl carbons of glucose and their pyrolysis products.

Oxidation derivative of (-)-epigallocatechin-3-gallate (EGCG) inhibits RANKL-induced osteoclastogenesis by suppressing RANK signaling pathways in RAW 264.7 cells

Tea consumption has positive effects on the skeletal system and prevents postmenopausal osteoporosis, mainly by inhibiting osteoclastogenesis. In green tea, (-)-epigallocatechin-3-gallate (EGCG) is the most abundant and active compound and has been shown to inhibit RANKL-induced osteoclast formation. Taking into account the highly oxidizable and unstable nature of EGCG, we hypothesized that EGCG oxidation product exhibits greater anti-osteoclastogenesis potential than EGCG. In this study, we successfully isolated and identified an EGCG oxidation derivative, (-)-gallocatechin gallate (compound 2), using a chemical oxidation strategy. We then compared the ability of compound 2 and EGCG to inhibit RANKL-induced osteoclastogenesis in RAW 264.7 cells. The results of TRAP staining and F-actin ring immunofluorescent staining showed that compound 2 exhibits stronger inhibition of RANKL-induced osteoclast differentiation and F-actin ring formation, respectively, than EGCG. Additionally, quantitative real-time PCR (qRT-PCR) and western blotting analyses showed that compound 2 significantly and more strongly inhibited the expression of osteoclastogenesis-related marker genes and proteins, including c-Src, TRAP, cathepsin K, β3-Integrin, and MMP-9, compared with EGCG. Furthermore, compound 2 significantly suppressed RANKL-induced expression of NFATc1 and c-Fos, the master transcriptional regulators of osteoclastogenesis, more strongly than EGCG. Mechanistically, molecular interaction assays showed that compound 2 binds to RANK with high affinity (KD = 189 nM) and blocks RANKL–RANK interactions, thereby suppressing RANKL-induced early RANK signaling pathways including p65, JNK, ERK, and p38 in osteoclast precursors. Taken together, this study demonstrates for the first time that an oxidation derivative of EGCG (compound 2) inhibits RANKL-induced osteoclastogenesis by suppressing RANK signaling pathways in RAW 264.7 cells.