Gallocatechin gallate

Gallocatechin gallate
Other names (-)-Gallocatechin gallate (2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate)
Identifiers
CAS number	4233-96-9
Jmol-3D images	Image 1
SMILES Oc1cc(cc(O)c1O)C(=O)O[C@@H]3Cc2c(cc(O)cc2O)O[C@H]3c4cc(O)c(O)c(O)c4
Properties
Molecular formula	C22H18O11
Molar mass	458.37 g mol−1
Exact mass	458.084911 u
Y gallate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

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 CGC (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 straight at 100 degrees Celsius.^[2]

References

1. ^ Ikeda, Ikuo; Kobayashi, Makoto; Hamada, Tadateru; Tsuda, Koichi; Goto, Hitomi; Imaizumi, Katsumi; Nozawa, Ayumu; Sugimoto, Akio et al. (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. 

This article about a natural phenol is a stub. You can help Wikipedia by expanding it.v · Categories: Flavanols Resorcinols Pyrogallols Benzoates Natural phenol stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем написать курсовую Epicatechin gallate N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate Look at other dictionaries: Epigallocatechin gallate — EGCG redirects here. For the software, see Extended GCG. Epigallocatechin gallate IUPAC name …   Wikipedia Epicatechin gallate — IUPAC name [(2R,3R) 2 (3,4 dihydroxyphenyl) 5,7 dihydroxy 3,4 dihydro 2H chromen 3 yl] 3,4,5 trihydroxybenzoate …   Wikipedia Gallocatechol — Other names epigallocatechin (+) gallocatechin …   Wikipedia Gallic acid — IUPAC name …   Wikipedia Catechin — IUPAC name (2R,3S) 2 (3,4 dihydroxyphenyl) 3,4 dihydro 2H chromene 3,5,7 …   Wikipedia Afzelechin — IUPAC name (2R,3R) 2 (4 hydroxyphenyl) 3,4 dihydro 2H chromene 3,5,7 triol …   Wikipedia Meciadanol — IUPAC name 2 (3,4 dihydroxyphenyl) 3 methoxy 3,4 dihydro 2H chromene 5,7 diol …   Wikipedia Mesquitol — IUPAC name 3,4 Dihydro 2alpha (3,4 dihydroxyphenyl) 2H 1 benzopyran 3beta,7,8 triol …   Wikipedia Flavonoid — The term flavonoid (or bioflavonoid) refers to a class of plant secondary metabolites. According to the IUPAC nomenclature, [http://www.iupac.org/goldbook/F02424.pdf Flavonoids (isoflavonoids and neoflavonoids).] , IUPAC Compendium of Chemical… …   Wikipedia Phenolic content in tea — Most of the polyphenols in Green tea are flavan 3 ols (catechins) Natural phenols and polyphenols are compounds found naturally in plants. A group of natural phenols called the flavonoids are of most popular interest because researchers have… …   Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”