Quebrachitol is a naturally occurring optically active
cyclitol
In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is or where 3 ≤ ''x'' ≤ ''n''.
The name is also used for c ...
, a cyclic polyol. It can be found in ''
Allophylus edulis
''Allophylus edulis'' ( pt, chal-chal) is a plant species in the genus ''Allophylus'' endemic to the Guianas, Brazil, Bolivia, Paraguay, Argentina and Uruguay.
Phytochemistry
Quebrachitol, a cyclitol, and viridiflorol, a sesquiterpenoid
Ses ...
'' and in the serum left after the coagulation of the ''
Hevea brasiliensis
''Hevea brasiliensis'', the Pará rubber tree, ''sharinga'' tree, seringueira, or most commonly, rubber tree or rubber plant, is a flowering plant belonging to the spurge family Euphorbiaceae
Euphorbiaceae, the spurge family, is a large fami ...
'' latex in the operation of
rubber tapping
Rubber tapping is the process by which latex is collected from a rubber tree. The latex is harvested by slicing a groove into the bark of the tree at a depth of with a hooked knife and peeling back the bark. Trees must be approximately six years ...
. It is also found in ''
Cannabis sativa
''Cannabis sativa'' is an annual Herbaceous plant, herbaceous flowering plant indigenous to East Asia, Eastern Asia, but now of cosmopolitan distribution due to widespread cultivation. It has been cultivated throughout recorded history, used as ...
'', in ''
Paullinia pinnata
''Paullinia pinnata'' is a flowering plant species in the genus of ''Paullinia'' found in South America and Africa.
The long flexible stems of ''P. pinnata'' are used to poison fish in shallow pools, as described by the English naturalist Henry ...
'' and in
seabuckthorn
''Hippophae'' is the genus of sea buckthorns, deciduous shrubs in the family Elaeagnaceae. The name sea buckthorn may be hyphenated to avoid confusion with the unrelated true buckthorns (''Rhamnus'', family Rhamnaceae). It is also referred to as ...
.
It was first isolated by
Tanret in 1887 from the bark of ''
Aspidosperma quebracho
''Aspidosperma quebracho-blanco'', commonly known as Quebracho blanco, kebrako, or white quebracho, is a South American tree species, native to Brazil, northern Argentina, Bolivia, Paraguay, and Uruguay. It must not be confused with other specie ...
''. 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
Diarrhea, also spelled diarrhoea, is the condition of having at least three loose, liquid, or watery bowel movements each day. It often lasts for a few days and can result in dehydration due to fluid loss. Signs of dehydration often begin wi ...
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.
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
/ref>
References
External links
*{{Cite web , url=http://www.sigmaaldrich.com/catalog/product/aldrich/s404551?lang=en®ion=US , title=Quebrachitol on the Sigma-Aldrich website , access-date=September 19, 2016 , archive-url=https://web.archive.org/web/20121003153319/http://www.sigmaaldrich.com/catalog/product/aldrich/s404551?lang=en®ion=US , archive-date=October 3, 2012 , url-status=bot: unknown , df=mdy-all
Cyclitols