Mesquitol

Mesquitol
Chemical structure of mesquitol
Chemical structure of mesquitol
Names
IUPAC name
(2R,3S)-Flavan-3,3′,4′,7,8-pentol
Systematic IUPAC name
(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,7,8-triol
Other names
(−)-mesquitol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C15H14O6/c16-9-3-1-7(5-11(9)18)14-12(19)6-8-2-4-10(17)13(20)15(8)21-14/h1-5,12,14,16-20H,6H2/t12-,14+/m0/s1 X markN
    Key: TXULLYMENMRLHL-GXTWGEPZSA-N X markN
  • InChI=1/C15H14O6/c16-9-3-1-7(5-11(9)18)14-12(19)6-8-2-4-10(17)13(20)15(8)21-14/h1-5,12,14,16-20H,6H2/t12-,14+/m0/s1
    Key: TXULLYMENMRLHL-GXTWGEPZBX
  • Oc1ccc(cc1O)[C@H]3Oc2c(O)c(O)ccc2C[C@@H]3O
Properties
C15H14O6
Molar mass 290.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

Mesquitol is a flavan-3-ol, a type of flavonoid.

Prosopis juliflora, an invasive New World mesquite now found in Kenya, has unusually high levels of (−)-mesquitol in its heartwood.

Mesquitol, with its pyrogallol-type A-ring, is more susceptible to quinone formation at this ring, leading to aryl–aryl bond formation at carbon 5. The structural moieties constitute the proteracacinidin class of proanthocyanidins. Mesquitol-(5→8)-catechin atropisomers can be isolated from Prosopis glandulosa.

References

  1. ↑ "Mesquitol". metabolomics.jp.
  2. ↑ Sirmah, Peter; Dumarçay, Stéphane; Masson, Eric; Gérardin, Philippe (January 2009). "Unusual amount of (−)-mesquitol from the heartwood of Prosopis juliflora". Natural Product Research. 23 (2): 183–189. doi:10.1080/14786410801940968.
  3. ↑ Ferreira, Daneel; Slade, Desmond (2002). "Oligomeric proanthocyanidins: naturally occurring O-heterocycles". Natural Product Reports. 19: 517–541. doi:10.1039/b008741f.
  4. ↑ Young, Esmé; Brandt, Edward V.; Young, Desmond A.; Ferreira, Daneel; Roux, David G. (1986). "Synthesis of condensed tannins. Part 17. Oligomeric (2R,3S)-3,3′,4′,7,8-pentahydroxyflavans: atropisomerism and conformation of biphenyl and m-terphenyl analogues from Prosopis glandulosa ('mesquite')". Journal of the Chemical Society, Perkin Transactions 1. 1986: 1737–1749. doi:10.1039/P19860001737.