Theogallin

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
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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/s1 checkY
    Key: LDPLFHGGZNSKDS-FTBFGRRBSA-N checkY
  • 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
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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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]

  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.[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.{{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.