10517-25-6

Basic information

• Product Name: (+)-catechin 3-O-gallate
• CAS NO: 10517-25-6
• Molecular Weight: 442.379
• Mol File: 10517-25-6.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (+)-catechin 3-O-gallate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-catechin 3-O-gallate(10517-25-6)
• EPA Substance Registry System: (+)-catechin 3-O-gallate(10517-25-6)

Safety Data

• Hazardous Substances Data: 10517-25-6(Hazardous Substances Data)

Upstream product

• 100-53-8 phenylmethanethiol 
• 1255211-38-1 platanoside-A 
• 108-98-5 thiophenol 
• 1255211-63-2 platanoside-B 
• 154-23-4 catechin 
• 918158-03-9 (1S,2S)-3-[2,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-(3,4-bis-benzyloxy-phenyl)-propane-1,2-diol 
• 918157-97-8 (E)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4-bis(benzyloxy)phenyl]propene 
• 732298-11-2 (+)-(1S,2S)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propane-1,2-diol 
• 732298-08-7 (E)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propene 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 1486-47-1 3,4,5-tris(benzyloxy)benzoyl chloride 
• 1486-48-2 3,4,5-tribenzyloxybenzoic acid 
• 63604-98-8 1,3-dibenzylphloroglucinol 
• 732298-13-4 (+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate 

Downstream Products

• 621-54-5 3-(3-hydroxyphenyl)-propanoic acid 
• 31129-95-0 5-(3′-hydroxyphenyl)valeric acid 
• 6500-64-7 5-(3'-methoxyphenyl)pentanoic acid 
• 31129-94-9 5-(3′,4′,5′-trihydroxyphenyl)valeric acid 
• 111397-00-3 (2S)-1-(3',4'-dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol 
• 191666-22-5 (4R)-5-(3,4-dihydroxyphenyl)-γ-valerolactone 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 30462-34-1 theaflavin-3-gallate 
• 1013313-02-4 theaflavate C 
• 1013313-04-6 bistheaflavate A 
• 89064-33-5 procyanidin B₄ 3'-O-gallate 
• 79907-44-1 procyanidin B₂-3,3'-di-O-gallate 
• 28543-07-9 theaflavin-3-gallate 
• 149-91-7 3,4,5-trihydroxybenzoic acid 

Relevant articles and documents

Potential O-acyl-substituted (-)-epicatechin gallate prodrugs as inhibitors of DMBA/TPA-induced squamous cell carcinoma of skin in swiss albino mice

(-)-Epicatechin-3-gallate (1) is one of the principal catechins of green tea and exhibits cancer-preventive activities in various animal models. However, this compound is unstable in neutral or alkaline medium and, therefore, has a poor bioavailability. To improve its stability, O-acyl derivatives of 1 were prepared by isolating the partially purified tea catechin fraction from green tea extract and treating it with a variety of acylating agents. The resulting derivatives, compounds 2-6, were screened for their antitumor potential against 7,12-dimethylbenz[a]anthracene (DMBA)/12-O-tetradecanoylphorbol-13-acetate (TPA)-induced squamous cell carcinogenesis of skin in mice. The results showed that the antitumor activity decreased with the increase in size of the chain length of the acyl groups, i.e., from compound 2, derivative with an Ac group, to compound 6, possessing a valeryl group. Moreover, the C4 derivative with a branched acyl chain, 5, had a lower activity than the linear C4 derivative 4. This reduction in the inhibitory activity may be due to the steric hindrance by the two Me groups. Moreover, significant increases in the protein levels analyzed by ELISA of c-Jun, p65, and p53 were observed in the skin of DMBA/TPA treated mice, whereas mice treated with 2 and DMBA/TPA had a similar expression of these transcription factors than the control mice. The prodrug potential of the O-acyl derivatives 2-6 showed that they were adequately stable to be absorbed intact from the intestine, more stable at gastric pH, and suitable for oral administration. Copyright

HYDROLYSABLE TANNINS AND PROANTHOCYANIDINS FROM GREEN TEA

Two hydrolysable tannins were isolated from green tea, and their structures were characterized by chemical and spectral means as 1,4,6-tri-O-galloyl-β-D-glucose and 1-O-galloyl-4,6-(-)-hexahydroxydiphenoyl-β-D-glucose.In addition, a new proanthocyanidin gallate was isolated, together with the known procyanidins B-2, B-4 and C-1.The structure of the proanthocyanidin was established as epigallocatechin-(4β -> 8)-3-O-galloylepicatechin.Key Word Index - Thea sinensis; Theaceae; green tea; ellagitannin; gallotannin; proanthocyanidin; polyphenol.

Oligomeric proanthocyanidin glycosides of Clementsia semenovii

Five new proanthocyanidins have been isolated from the roots of Clementsia semenovii A. Bor. The structures of two of these compounds have been established by various chemical and physical methods: 7-0-[6-0-galloyl-β-D-Glcp →6 O-βD-Glcp →6O-β-D-Glcp → 6O-β-D-Glcp]-(+)-gallocatechin-(4α-8)-(+)-gallocatechin- (4α-8)-(-)-epigallocatechin-(4β-8)-(-)-epigallocatechin-(4β-8)- (-) -epigallocatechin-(4β-8)-(+)-catechin - CS-1 and 3-O-galloyl-7-O-(β-D-Glcp → 6O-β-D-Glcp)-(-)-epigallocatechin-(4β-8)-[3-O-galloyl-(-)- epigallocatechin]-(4β-8)-[3-O-galloyl-(-)-epigallocatechin]-(4β-8)-[3- O-galloyl-5-O-(6-O-galloyl-O-β-D-Glcp)]-(-)-epicatechin - CS-2.

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.