Linderatin
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| Chemical and physical data | |
| Formula | C25H30O4 |
| Molar mass | 394.511 g·mol−1 |
| 3D model (JSmol) | |
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Linderatin and linderatone are two flavonoids from the leaves of Lindera umbellata var. lancea and L. umbellata.[1][2]
Linderatin has patented use as a skin whitening (depigmentation) agent.[3]
Synthesis
The Hoesch reaction between hydrocinnamonitrile (2-phenylethylcyanide) [645-59-0] (1) with phloroglucinol [108-73-6] (2) gives 3-phenylpropanoyl-phloroglucinol [1088-08-0] (3). Treatment with menthadiene (alpha-phellandrene) [99-83-2] (4) completes the synthesis of linderatin (5).
See also
References
- ^ Ichino, K., Tanaka, H., Ito, K. (November 1988). "ChemInform Abstract: Two Novel Flavonoids from the Leaves of Lindera umbellata var. lancea and L. umbellata". ChemInform. 19 (44): chin.198844339. doi:10.1002/chin.198844339.
- ^ Tanaka, Hitoshi; Ichino, Kazuhiko; Ito, Kazuo (1984). "A novel dihydrochalcone, linderatin from Lindera umbellata var. lancea". CHEMICAL & PHARMACEUTICAL BULLETIN. 32 (9): 3747–3750. doi:10.1248/cpb.32.3747.
- ^ US9629786 idem Anne Mandeau, et al., WO2012098134 (to Pierre Fabre Dermo Cosmetique SA).
- ^ Mustafa, Kamarul'Ain; Kjaergaard, Henrik G; Perry, Nigel B; Weavers, Rex T (2003). "Hydrogen-bonded rotamers of 2′,4′,6′-trihydroxy-3′-formyldihydrochalcone, an intermediate in the synthesis of a dihydrochalcone from Leptospermum recurvum". Tetrahedron. 59 (32): 6113–6120. doi:10.1016/S0040-4020(03)00940-2
- ^ Crombie, Leslie; Crombie, W. Mary L.; Firth, David F. (1988). "Terpenylations using (R)-(–)-α-phellandrene. Synthesis of the (3S,4R)-8,9-dihydro-o- and -p-cannabidiols, their iso-THC's, and the natural dihydrochalcone (3S,4R)-(+)-linderatin". J. Chem. Soc., Perkin Trans. 1 (5): 1251–1253. doi:10.1039/P19880001251.
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