Quebrachitol

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
CAS Number	642-38-6 N=
3D model (JSmol)	Interactive image
ChemSpider	10254652 Y
PubChem CID	151108
InChI InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1 Y Key: DSCFFEYYQKSRSV-FIZWYUIZSA-N Y
SMILES CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H]([C@H]1O)O)O)O)O
Properties
Chemical formula	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)
Solubility in water	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).
N  (what is YN ?)
Infobox references

Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. It can be found in Allophylus edulis and in the serum left after the coagulation of the Hevea brasiliensis latex in the operation of rubber tapping. It is also found in Cannabis sativa, in Paullinia pinnata and in seabuckthorn.

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.

Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials. For example, its conversion into antifungal (E)-β-methoxyacrylate, oudemansin X has been made.