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Theogallin

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Theogallin
Chemical structure of theogallin
Names
Preferred IUPAC name (1S,3R,4R,5R)-1,3,4-Trihydroxy-5-cyclohexane-1-carboxylic acid
Other names 3-O-Galloylquinic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H16O10/c15-6-1-5(2-7(16)10(6)18)12(20)24-9-4-14(23,13(21)22)3-8(17)11(9)19/h1-2,8-9,11,15-19,23H,3-4H2,(H,21,22)/t8-,9-,11-,14+/m1/s1Key: LDPLFHGGZNSKDS-FTBFGRRBSA-N
SMILES
  • O=C(O)2(O)C(O)(O)(OC(=O)c1cc(O)c(O)c(O)c1)C2
Properties
Chemical formula C14H16O10
Molar mass 344.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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

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. Bibcode:1954JSFA....5..593C. 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. Vol. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. S2CID 33938157.
Phenolic acids (C6-C1) and their glycosides
Monohydroxybenzoic acids
Glycosides
Alkylated
Dihydroxybenzoic acids
Alkylated
Trihydroxybenzoic acids
Glycosides
Alkylated
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