Chemistry:Theogallin

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Theogallin
Chemical structure of theogallin
Names
Preferred IUPAC name
(1S,3R,4R,5R)-1,3,4-Trihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]cyclohexane-1-carboxylic acid
Other names
3-O-Galloylquinic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
Properties
C14H16O10
Molar mass 344.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Theogallin is a trihydroxybenzoic acid glycoside, a type of polyphenolic compound found in tea[1] where it has been characterised as an umami enhancing compound.[2] The compound can also be found in Arbutus unedo fruits.[3]

In rats, theogallin, or its metabolite quinic acid, can move through the blood brain barrier and can have cognition enhancing activities.[4]

References

  1. Cartwright, R. A.; Roberts, E. A. H. (1954). "Theogallin, a polyphenol occurring in tea". Journal of the Science of Food and Agriculture 5 (12): 593. doi:10.1002/jsfa.2740051207. 
  2. Kaneko, S; Kumazawa, K; Masuda, H; Henze, A; Hofmann, T (2006). "Sensory and structural characterisation of an umami enhancing compound in green tea (mat-cha)". Flavour Science - Recent Advances and Trends. Developments in Food Science. 43. pp. 181. doi:10.1016/S0167-4501(06)80043-9. ISBN 978-0-444-52742-4. [|permanent dead link|dead link}}]
  3. Pawlowska, A.M., De Leo, M., Braca, A. (2006). "Phenolics of Arbutus unedo L. (Ericaceae) fruits: identification of anthocyanins and gallic acid derivatives". J. Agric. Food Chem. 54 (26): 10234–8. doi:10.1021/jf062230o. PMID 17177565. http://www.wikigenes.org/e/ref/e/17177565.html. 
  4. Dimpfel, Wilfried; Kler, Adolf; Kriesl, Erwin; Lehnfeld, Romanus (2007). "Theogallin and l-theanine as active ingredients in decaffeinated green tea extract: II. Characterization in the freely moving rat by means of quantitative field potential analysis". Journal of Pharmacy and Pharmacology 59 (10): 1397–403. doi:10.1211/jpp.59.10.0010. PMID 17910815.