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Gallocatechin gallate

Gallocatechin gallate (GCG) is the ester of gallocatechin and gallic acid and a type of catechin. It is an epimer of epigallocatechin gallate (EGCG).

Gallocatechin gallate
Names
IUPAC name
(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)
Other names
(-)-Gallocatechin gallate
Identifiers
  • 5127-64-0 N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:156271
ChemSpider
  • 172662 N
  • 199472
UNII
  • 0C056HB16M N
  • InChI=1S/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 N
    Key: WMBWREPUVVBILR-NQIIRXRSSA-N N
  • 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
    Key: WMBWREPUVVBILR-NQIIRXRSBC
  • C1[C@H]([C@@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
Properties
C22H18O11
Molar mass 458.375 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

In a high temperature environment, an epimerization change is likely to occur, because heating results in the conversion from EGCG to GCG.[1] According to the referenced study the resulting GCG (the epimer of EGCG) results in even lower dietary cholesterol absorption than occurs with EGCG. While this may be a beneficial outcome with respect to cholesterol reduction activity, for those wishing to maximize the EGCG content of green tea infusions, it is still appropriate to use high temperatures, as long as it is taking into account that extreme conditions will lead to small reductions in total EGCG, for example a 12.4% reduction in total EGCG when heated for 30 minutes at 100 °C.[2]

References edit

  1. ^ Ikeda, Ikuo; Kobayashi, Makoto; Hamada, Tadateru; Tsuda, Koichi; Goto, Hitomi; Imaizumi, Katsumi; Nozawa, Ayumu; Sugimoto, Akio; Kakuda, Takami (2003). "Heat-Epimerized Tea Catechins Rich in Gallocatechin Gallate and Catechin Gallate Are More Effective to Inhibit Cholesterol Absorption than Tea Catechins Rich in Epigallocatechin Gallate and Epicatechin Gallate". Journal of Agricultural and Food Chemistry. 51 (25): 7303–7. doi:10.1021/jf034728l. PMID 14640575.
  2. ^ Wang, Rong; Zhou, Weibiao; Jiang, Xiaohui (2008). "Reaction Kinetics of Degradation and Epimerization of Epigallocatechin Gallate (EGCG) in Aqueous System over a Wide Temperature Range". Journal of Agricultural and Food Chemistry. 56 (8): 2694–701. doi:10.1021/jf0730338. PMID 18361498.


gallocatechin, gallate, ester, gallocatechin, gallic, acid, type, catechin, epimer, epigallocatechin, gallate, egcg, namesiupac, name, trihydroxyphenyl, dihydro, benzopyran, triol, trihydroxybenzoate, other, names, identifierscas, number, 5127, model, jsmol, i. Gallocatechin gallate GCG is the ester of gallocatechin and gallic acid and a type of catechin It is an epimer of epigallocatechin gallate EGCG Gallocatechin gallate NamesIUPAC name 2S 3R 2 3 4 5 Trihydroxyphenyl 3 4 dihydro 1 2H benzopyran 3 5 7 triol 3 3 4 5 trihydroxybenzoate Other names Gallocatechin gallateIdentifiersCAS Number 5127 64 0 N3D model JSmol Interactive imageChEBI CHEBI 156271ChemSpider 172662 NPubChem CID 199472UNII 0C056HB16M NInChI InChI 1S 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 NKey WMBWREPUVVBILR NQIIRXRSSA N NInChI 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 s1Key WMBWREPUVVBILR NQIIRXRSBCSMILES C1 C H C H OC2 CC CC C21 O O C3 CC C C C3 O O O OC O C4 CC C C C4 O O OPropertiesChemical formula C 22H 18O 11Molar mass 458 375 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references In a high temperature environment an epimerization change is likely to occur because heating results in the conversion from EGCG to GCG 1 According to the referenced study the resulting GCG the epimer of EGCG results in even lower dietary cholesterol absorption than occurs with EGCG While this may be a beneficial outcome with respect to cholesterol reduction activity for those wishing to maximize the EGCG content of green tea infusions it is still appropriate to use high temperatures as long as it is taking into account that extreme conditions will lead to small reductions in total EGCG for example a 12 4 reduction in total EGCG when heated for 30 minutes at 100 C 2 References edit Ikeda Ikuo Kobayashi Makoto Hamada Tadateru Tsuda Koichi Goto Hitomi Imaizumi Katsumi Nozawa Ayumu Sugimoto Akio Kakuda Takami 2003 Heat Epimerized Tea Catechins Rich in Gallocatechin Gallate and Catechin Gallate Are More Effective to Inhibit Cholesterol Absorption than Tea Catechins Rich in Epigallocatechin Gallate and Epicatechin Gallate Journal of Agricultural and Food Chemistry 51 25 7303 7 doi 10 1021 jf034728l PMID 14640575 Wang Rong Zhou Weibiao Jiang Xiaohui 2008 Reaction Kinetics of Degradation and Epimerization of Epigallocatechin Gallate EGCG in Aqueous System over a Wide Temperature Range Journal of Agricultural and Food Chemistry 56 8 2694 701 doi 10 1021 jf0730338 PMID 18361498 nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Gallocatechin gallate amp oldid 1099852838, wikipedia, wiki, book, books, library,

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