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Theogallin

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Theogallin
Names
Chemical structure of theogallin
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-Galloyl quinic acid
Identifiers
CAS Number	17365-11-6^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9522^Y
ChemSpider	391291^Y
PubChem CID	442988
UNII	N8GTS57R32^Y
CompTox Dashboard(EPA)	DTXSID60332031
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/s1^Y Key: LDPLFHGGZNSKDS-FTBFGRRBSA-N^Y
SMILES 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
Chemical formula	C₁₄H₁₆O₁₀
Molar mass	344.27 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

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

In rats, theogallin, or its metabolitequinic acid, can move through theblood brain barrier and can have cognition enhancing activities.^[4]

^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.
^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]}
^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)
^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

Glycosides	p-Hydroxybenzoic acid glucoside
Alkylated	Methylparaben (Methyl-p-hydroxybenzoic acid)

Alkylated	Ethyl protocatechuate Orsellinic acid

Glycosides	Bergenin Norbergenin Theogallin Chebulic acid
Alkylated	Ethyl gallate Eudesmic acid Methyl gallate Syringic acid

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