Theaflavin

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Theaflavin
Theaflavin.svg
Theaflavin 3D BS.png
Names
Preferred IUPAC name
3,4,5-Trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-6H-benzo[7]annulen-6-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)/t21-,22-,28-,29-/m1/s1 checkY
    Key: IPMYMEWFZKHGAX-ZKSIBHASSA-N checkY
  • InChI=1/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)/t21-,22-,28-,29-/m1/s1
    Key: IPMYMEWFZKHGAX-ZKSIBHASBU
  • c1c(cc(=O)c(c2c1c(cc(c2O)O)[C@@H]3[C@@H](Cc4c(cc(cc4O3)O)O)O)O)[C@@H]5[C@@H](Cc6c(cc(cc6O5)O)O)O
Properties
C29H24O12
Molar mass 564.499 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Theaflavin (TF) and its derivatives, known collectively as theaflavins, are antioxidant polyphenols that are formed from the condensation of flavan-3-ols in tea leaves during the enzymatic oxidation (sometimes erroneously referred to as fermentation) of black tea. Theaflavin-3-gallate, theaflavin-3'-gallate, and theaflavin-3-3'-digallate are the main theaflavins.[1] Theaflavins are types of thearubigins, and are therefore reddish in color. Those molecules contain a tropolone moiety.


Certain benefits of black tea containing TFs can include the ability to whiten skin in cosmetics[2] and support antiobesity by affecting lipid metabolism.[3][4] The radical scavenging function remains under investigation.[5]

See also[edit]

References[edit]

  1. ^ "Theaflavin Effectiveness, Safety, and Drug Interactions on RxList". rxlist.com. Archived from the original on 4 September 2017. Retrieved 24 April 2018.
  2. ^ Y. C. Kim, S. Y. Choi, and E. Y. Park, “Anti-melanogenic effects of black, green, and white tea extracts on immortalized melanocytes,”Journal of Veterinary Science, vol. 16, no. 2, p. 135, 2015.
  3. ^ P. J. Park, C.-S. Rha, and S. T. Kim, “Theaflavin-enriched fraction stimulates adipogenesis in human subcutaneous fat cells,”International Journal of Molecular Sciences, vol. 20, no. 8, p. 2034, 2019.
  4. ^ Shan Z, Nisar M, Li M, Zhang C, Wan C. Theaflavin Chemistry and Its Health Benefits Oxidative Medicine and Cellular Longevity. 2021 Jan;2021. PMCID: PMC8601833.
  5. ^ Vu, Huyen Trang; Song, Fu V.; Tian, Kun V.; Chass, Gregory A. (2019). "Systematic characterisation of the structure and radical scavenging potency of Pu'Er tea (普洱) polyphenol theaflavin". Organic & Biomolecular Chemistry. 17 (46): 9942–9950. doi:10.1039/C9OB02007A. PMID 31729510.