Theogallin

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Theogallin
Chemical structure of theogallin
IUPAC name

(1S,3R,4R,5R)-1,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxycyclohexane-1-carboxylic acid

Other names

3-O-Galloylquinic acid

Identifiers
CAS number 17365-11-6 N
PubChem 442988
ChemSpider 391291 YesY
ChEBI CHEBI:9522 YesY
Jmol-3D images {{#if:O=C(O)[C@]2(O)C[C@@H](O)[C@@H](O)[C@H](OC(=O)c1cc(O)c(O)c(O)c1)C2|Image 1
Properties
Molecular formula C14H16O10
Molar mass 344.27 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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. p. 181. doi:10.1016/S0167-4501(06)80043-9. ISBN 978-0-444-52742-4. 
  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. 
  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. 
Phenolic acids and their glycosides
Monohydroxybenzoic acids
Aglycones
Glycosides
  • p-Hydroxybenzoic acid glucoside
Dihydroxybenzoic acids
Trihydroxybenzoic acids
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