2596-50-1

Basic information

• Product Name: (-)-gallocatechin 3-gallate
• CAS NO: 2596-50-1
• Molecular Weight: 458.378
• Mol File: 2596-50-1.mol
• Article Data: 35

Chemical Properties

• CAS DataBase Reference: (-)-gallocatechin 3-gallate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-gallocatechin 3-gallate(2596-50-1)
• EPA Substance Registry System: (-)-gallocatechin 3-gallate(2596-50-1)

Safety Data

• Hazardous Substances Data: 2596-50-1(Hazardous Substances Data)

Upstream product

• 332386-77-3 (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate 
• 402493-24-7 3,4,5-Trihydroxy-benzoic acid (2R,3S,4S)-5,7-dihydroxy-4-phenylsulfanyl-2-(3,4,5-trihydroxy-phenyl)-chroman-3-yl ester 
• 121844-27-7 assamicain B 
• 100-53-8 phenylmethanethiol 
• 121795-66-2 assamicain A 
• 121795-67-3 assamicain C 
• 126715-91-1 epicatechin 3-O-gallate-(4β->6)-epigallocatechin 3-O-gallate 
• 332386-71-7 (-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol 
• 332386-74-0 (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol 
• 1486-47-1 3,4,5-tris(benzyloxy)benzoyl chloride 
• 1486-48-2 3,4,5-tribenzyloxybenzoic acid 
• 86588-88-7 (2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin-3''-O-gallate 
• 225793-49-7 EGCg quinone dimer A 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 989-51-5 (-)-gallocatechin 3-gallate 
• 2596-50-1 (-)-epigallocathechin gallate 
• 1608504-12-6 C₂₁H₁₉NO₈S 
• 1256160-11-8 (2R,3R)-5,7-bis(hydroxyl)-2-[3',4',5'-tris(hydroxy)phenyl]chroman-3-yl 4-fluorobenzoate 
• 1256160-12-9 (2R,3R)-5,7-bis(hydroxyl)-2-[3',4',5'-tris(hydroxy)phenyl]chroman-3-yl 3,4-difluorobenzoate 
• 1608504-26-2 C₅₂H₈₇FO₈Si₅ 
• 1608504-27-3 C₅₂H₈₆F₂O₈Si₅ 
• 1608504-28-4 C₅₁H₈₇NO₈Si₅ 
• 1608504-29-5 C₅₂H₉₄O₈Si₅ 

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

Molecular Mechanism by Which Tea Catechins Decrease the Micellar Solubility of Cholesterol

Tea polyphenols lower the levels of cholesterol in the blood by decreasing the cholesterol micellar solubility. To clarify this mechanism, the interactions between taurocholic acid and (-)-epigallocatechin gallate (EGCg) and its derivatives were investigated. 13C NMR studies revealed remarkable chemical-shift changes for the carbonyl carbon atom and the 1″- and 4″-positions in the galloyl moiety. Furthermore, 1H NMR studies using (-)-EGCg derivatives showed that the number of hydroxyl groups on the B ring did not affect these interactions, whereas the carbonyl carbon atom and the aromatic ring of the galloyl moiety had remarkable effects. The configuration at the 2- and 3-positions of the catechin also influenced these interactions, with the trans-configuration resulting in stronger inhibition activity than the cis-configuration. Additionally, a 1:1 component ratio for the catechin-taurocholic acid complex was determined by electrospray ionization-mass spectrometry. These molecular mechanisms contribute to the development of cholesterol-absorption inhibitors.

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.