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quebrachitol
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Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. It can be found in ''Allophylus edulis''〔(First record of l-quebrachitol in Allophylus edulis (Sapindaceae). Martina Díaz, Andrés González, Ian Castro-Gamboa, David Gonzalez and Carmen Rossini, Carbohydrate Research, Volume 343, Issue 15, 13 October 2008, Pages 2699-2700, ) 〕 and in the serum left after the coagulation of the ''Hevea brasiliensis'' latex in the operation of rubber tapping.〔(Quebrachitol. Jan van Alphen, Ind. Eng. Chem., 1951, 43 (1), pp 141–145, ) 〕 It is also found in ''Cannabis sativa'',〔(1955 - ACTA UNIVERSITATIS PALACKIANAE OLOMUCENSIS - TOM. VI. - HEMP AS A MEDICAMENT, Properties of isolated substances. Prof. Jan Kabelik, A brief survey of the methods of isolation and the physical and chemical properties and structures of the isolated antibacterial substances. F. Santavy & Z. Krejci )〕 in ''Paullinia pinnata'' and in seabuckthorn.〔(Some new data about antiviral and related activities of seabuckthorn principals and the prospects of their use. Shipulina L.D., All-Russian Research Institute of Medicinal and Aromatic Plants, Moscow, Russia )〕
It was first isolated by Tanret in 1887 from the bark of ''Aspidosperma quebracho''. The substance was tested as a sweetening agent for diabetics in 1933. It shows a sweetening property half of that of sucrose but induces colic or diarrhoea at concentration used to render the food palatable.〔(An investigation of quebrachitol as a sweetening agent for diabetics. Robert Alexander McCance and Robert Daniel Lawrence, Biochem J. 1933; 27(4): 986–989 )〕
Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials.〔(Quebrachitol: A Versatile Building Block in the Construction of Naturally Occurring Bioactive Materials. James J. Kiddle, Chem. Rev., 1995, 95 (6), pp 2189–2202, ) 〕 For example, its conversion into antifungal (E)-β-methoxyacrylate, oudemansin X has been made.〔(Total synthesis of antibiotic (−)-oudemansin X utilizing L-quebrachitol as a chiral pool. Chida N., Yamada K. and Ogawa S., Chemistry Letters, 1992, no4, pp. 687-690 )〕
== References ==
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