Cyclitol
Encyclopedia
Cyclitols are cycloalkane
Cycloalkane
Cycloalkanes are types of alkanes that have one or more rings of carbon atoms in the chemical structure of their molecules. Alkanes are types of organic hydrocarbon compounds that have only single chemical bonds in their chemical structure...

s containing one hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...

 group on three or more ring atoms. They are cyclic polyol
Polyol
A polyol is an alcohol containing multiple hydroxyl groups. In two technological disciplines the term "polyol" has a special meaning: food science and polymer chemistry.- Polyols in food science :...

s. Cyclitols are one of the compatible solutes
Osmoprotectant
Osmoprotectants or compatible solutes are small molecules that act as osmolytes and help organisms survive extreme osmotic stress. Examples include betaines, amino acids, and the sugar trehalose. These molecules accumulate in cells and balance the osmotic difference between the cell's surroundings...

 which are formed in a plant as a response to salt or water stress. Some cyclitol (e.g quinic
Quinic acid
Quinic acid is a cyclitol, a cyclic polyol. It is a crystalline acid obtained from cinchona bark, coffee beans, and other plant products and made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee...

 or shikimic acid
Shikimic acid
Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi , from which it was first isolated....

) are parts of hydrolysable tannin
Hydrolysable tannin
A hydrolyzable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids....

s.

Naturally occurring cyclitols

  • Bornesitol
    Bornesitol
    Bornesitol is a cyclitol. It can be found in the gentianaceae and menyanthaceae plant families. Chemically, it is a methyl ether of D-myo-inositol....

  • Conduritol
    Conduritol
    Conduritol or 1,2,3,4-cyclohexenetetrol is any of six isomeric organic compounds with chemical formula C6H10O4, that can be seen as derivatives of cyclohexene with four hydroxyl groups replacing hydrogen atoms on the four carbon atoms not adjacent to the double bond...

  • Inositol
    Inositol
    Inositol or cyclohexane-1,2,3,4,5,6-hexol is a chemical compound with formula 6126 or 6, a sixfold alcohol of cyclohexane. It exists in nine possible stereoisomers, of which the most prominent form, widely occurring in nature, is cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol...

  • Ononitol
    Ononitol
    Ononitol is a cyclitol. It is a 4-O-methyl-myo-inositol and is a constituent of Medicago sativa....

     (4-O-methyl-myo-inositol)
  • Pinitol
    Pinitol
    Pinitol is a cyclitol, a cyclic polyol. It is a known anti-diabetic agent isolated from Sutherlandia frutescens leaves. Gall plant tannins can be differentiated by their content of pinitol....

     (3-O-methyl-chiro-inositol)
  • Pinpollitol
    Pinpollitol
    Pinpollitol is a cyclitol. It is a di-O-methyl--chiro-inositol that can be isolated from Pinus radiata....

     (di-O-methyl -(+)-chiro-inositol)
  • Quebrachitol
    Quebrachitol
    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. It is also found in Cannabis sativa and in seabuckthorn.It was first isolated by Tanret in 1887 from...

     (2-0-methyl-chiro-inositol)
  • Quinic acid
    Quinic acid
    Quinic acid is a cyclitol, a cyclic polyol. It is a crystalline acid obtained from cinchona bark, coffee beans, and other plant products and made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee...

  • Shikimic acid
    Shikimic acid
    Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi , from which it was first isolated....

  • Valienol
    Valienol
    Valienol is a C-7 cyclitol similar in structure to valienamine....

  • Viscumitol
    Viscumitol
    Viscumitol is a cyclitol. It is a dimethyl-ether of muco-inositol that can be isolated from Viscum album....

    (dimethyl-ether-muco-inositol)

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