Theogallin

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
PubChem 442988
ChemSpider 391291 Y
ChEBI CHEBI:9522
Jmol-3D images Image 1
Properties
Molecular formula C14H16O10
Molar mass 344.27 g/mol
Exact mass 344.074347 u
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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. pp. 181. doi:10.1016/S0167-4501(06)80043-9. ISBN 9780444527424. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B8G60-4NTHF8G-1H&_user=10&_coverDate=12%2F31%2F2006&_rdoc=1&_fmt=high&_orig=search&_origin=search&_sort=d&_docanchor=&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=cf813e5aaeb56a06c0f4828eac21dd0f&searchtype=a. 
  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. 
Monohydroxybenzoic acids
Dihydroxybenzoic acids
Trihydroxybenzoic acids