Mesquitol

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 ☒N
    Key: TXULLYMENMRLHL-GXTWGEPZSA-N ☒N
  • 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).
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Mesquitol is a flavan-3-ol, a type of flavonoid.[1]

Prosopis juliflora, an invasive New World mesquite now found in Kenya, has unusually high levels of (-)-mesquitol in its heartwood.[2]

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.[3] Mesquitol-(5→8)-catechin atropisomers can be isolated from Prosopis glandulosa.[4]

  1. ^ Mesquitol on metabolomics.jp
  2. ^ Unusual amount of (-)-mesquitol from the heartwood of Prosopis juliflora. Sirmah Peter, Dumarcay Stephane, Masson Eric and Gerardin Philippe, Natural Product Research, January 2009, Volume 23, Number 2, pages 183-189, doi:10.1080/14786410801940968
  3. ^ Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Daneel Ferreira and Desmond Slade, Nat. Prod. Rep., 2002, volume 19, pages 517–541, doi:10.1039/b008741f
  4. ^ 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’). Esmé Young, Edward V. Brandt, Desmond A. Young, Daneel Ferreira and David G. Roux, J. Chem. Soc., Perkin Trans. 1, 1986, pages 1737-1749, doi:10.1039/P19860001737