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Gallocatechol

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Gallocatechol
Names
Other names
(+)-gallocatechin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
MeSH Gallocatechol
UNII
  • InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1 ☒N
    Key: XMOCLSLCDHWDHP-SWLSCSKDSA-N ☒N
  • InChI=1/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1
    Key: XMOCLSLCDHWDHP-SWLSCSKDBQ
  • C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O
Properties
C15H14O7
Molar mass 306.270 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 checkY☒N ?)

Gallocatechol or gallocatechin (GC) is a flavan-3-ol, a type of chemical compound including catechin, with the gallate residue being in an isomeric trans position. It is one of the antioxidant chemicals found in food.

This compound possesses two epimers. The most common, (+)-gallocatechin (GC), CAS number 970-73-0, is found notably in green tea. Other sources of (+)-gallocatechin are bananas,[1] persimmons, and pomegranates.[citation needed] The other enantiomer is called (-)-gallocatechin or ent-gallocatechin.

It was first isolated from green tea by Michiyo Tsujimura in 1934.[2]

This compound had been shown to have moderate affinity to the human cannabinoid receptor,[3] which may contribute to the health benefits found by consuming green tea.

Epigallocatechin is another type of catechin, with the gallate residue being in an isomeric cis position. It can be found in St John's wort.[4]

See also

References

  1. ^ Someya, Shinichi; Yoshiki, Yumiko; Okubo, Kazuyoshi (2002). "Antioxidant compounds from bananas (Musa Cavendish)". Food Chemistry. 79 (3): 351–354. doi:10.1016/S0308-8146(02)00186-3.
  2. ^ "Michiyo Tsujimura (1888–1969)". Ochanomizu University. Retrieved 10 November 2015.
  3. ^ Korte, G.; Dreiseitel, A.; Schreier, P.; Oehme, A.; Locher, S.; Geiger, S.; Heilmann, J.; Sand, P. (2010). "Tea catechins' affinity for human cannabinoid receptors". Phytomedicine. 17 (1): 19–22. doi:10.1016/j.phymed.2009.10.001. PMID 19897346.
  4. ^ Wei, Yun; Xie, Qianqian; Dong, Wanting; Ito, Yoichiro (2009). "Separation of epigallocatechin and flavonoids from Hypericum perforatum L. By high-speed counter-current chromatography and preparative high-performance liquid chromatography". Journal of Chromatography A. 1216 (19): 4313–4318. doi:10.1016/j.chroma.2008.12.056. PMC 2777726. PMID 19150073.
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