Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. It can be found in Allophylus edulis[1] and in the serum left after the coagulation of the Hevea brasiliensis latex in the operation of rubber tapping.[2] It is also found in Cannabis sativa,[3] in Paullinia pinnata and in seabuckthorn.[4]
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IUPAC name
(1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
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Other names
Quebrachitol
L-Quebrachitol (-)-Quebrachitol 2-O-methyl-l-inositol 2-0-methyl-chiro-inositol | |
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Properties | |
C7H14O6 | |
Molar mass | 194.18 g/mol |
Appearance | White to off-white powder |
Melting point | 190 to 198 °C (374 to 388 °F; 463 to 471 K) |
Soluble in DMSO, dimethyl formamide, or water | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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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.[5]
Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials.[6] For example, its conversion into antifungal (E)-β-methoxyacrylate, oudemansin X has been made.[7]
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