Mesquitol (original) (raw)
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Mesquitol
 Chemical structure of mesquitol |
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| Names | |
| IUPAC name (2_R_,3_S_)-Flavan-3,3′,4′,7,8-pentol | |
| Systematic IUPAC name (2_R_,3_S_)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2_H_-1-benzopyran-3,7,8-triol | |
| Other names(−)-mesquitol | |
| Identifiers | |
| CAS Number | 109671-55-8  Y |
| 3D model (JSmol) | Interactive image |
| ChemSpider | 9208756  N |
| PubChem CID | 11033582 |
| UNII | 584GQF2MLB Y |
| CompTox Dashboard (EPA) | DTXSID10551896  |
| InChI 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 NKey: TXULLYMENMRLHL-GXTWGEPZSA-N NInChI=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/s1Key: TXULLYMENMRLHL-GXTWGEPZBX |
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| SMILES Oc1ccc(cc1O)[C@H]3Oc2c(O)c(O)ccc2C[C@@H]3O | |
| 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]
- ^ "Mesquitol". metabolomics.jp.
- ^ 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.
- ^ Ferreira, Daneel; Slade, Desmond (2002). "Oligomeric proanthocyanidins: naturally occurring _O_-heterocycles". Natural Product Reports. 19: 517–541. doi:10.1039/b008741f.
- ^ Young, Esmé; Brandt, Edward V.; Young, Desmond A.; Ferreira, Daneel; Roux, David G. (1986). "Synthesis of condensed tannins. Part 17. Oligomeric (2_R_,3_S_)-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.