Theaflavin

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.

Theaflavin
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 Y
    Key: IPMYMEWFZKHGAX-ZKSIBHASSA-N Y
  • 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 YN ?)
Infobox references

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]

See also

  • Theaflavin 3-gallate

References

  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.
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