Mesquitol
Names | |
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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 | |
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Properties | |
Chemical formula | 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). N verify (what is YN ?) Infobox references |
Chemical compound
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]
References
- ^ Mesquitol on metabolomics.jp
- ^ 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
- ^ Oligomeric proanthocyanidins: naturally occurring O-heterocycles. Daneel Ferreira and Desmond Slade, Nat. Prod. Rep., 2002, volume 19, pages 517–541, doi:10.1039/b008741f
- ^ 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
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Flavan-3-ols and their glycosides
- Afzelechin
- Catechin (Epicatechin)
- Epicatechin gallate
- Epigallocatechin
- Fisetinidol
- Gallocatechin
- Guibourtinidol
- Mesquitol
- Oritin
- Robinetinidol
- Meciadanol (3-O-methylcatechin)
- Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)
- 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
- (+)-Catechin 7-O-β-D-xylopyranoside
- Epicatechin-3′-O-glucoside
- Glochiflavanoside A, B, C D
- Polydine ((+)-catechin 7-O-α-L-arabinoside)
- Symplocoside (3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
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