Mesquitol

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Mesquitol
IUPAC name

3,4-Dihydro-2alpha- (3,4-dihydroxyphenyl) -2H-1-benzopyran-3beta,7,8-triol

Other names

(-)-mesquitol

Identifiers
CAS number 109671-55-8
PubChem 11033582
Jmol-3D images Image 1
Properties
Molecular formula C15H14O6
Molar mass 290.26 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Mesquitol is a flavan-3-ol, a type of flavonoid.[1]

Prosopis juliflora, a mesquite found in Kenya, shows unusual amount of (-)-mesquitol from 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]

References

  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
Flavan-3-ols and their glycosides
Flavan-3-ols
O-methylated flavan-3ols
  • Meciadanol (3-O-methylcatechin)
  • Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
Glycosides
  • Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside)
  • Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside)
  • Catechin-3-O-glucoside
  • Catechin-3'-O-glucoside
  • Catechin-4'-O-glucoside
  • Catechin-5-O-glucoside
  • Catechin-7-O-glucoside
Acetylated
Misc.


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