Quebrachitol

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quebrachitol
Chemical structure of quebrachitol
Names
IUPAC name
(1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
Other names
Quebrachitol
L-Quebrachitol
(-)-Quebrachitol
2-O-methyl-l-inositol
2-0-methyl-chiro-inositol
Identifiers
642-38-6 N=
ChEMBL ChEMBL501109 YesY
ChemSpider 10254652 YesY
Jmol-3D images Image
PubChem 151108
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

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 of 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]

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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