Cyclitol Esters
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Cyclitol Esters
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 compounds that can be viewed as result of substituting various functional groups for the hydrogen atoms in such a molecule, as well as similar molecules with one or more double bonds in the ring. Cyclitols and their derivatives are some of the compatible solutes which are formed in a plant as a response to salt or water stress. Some cyclitols (e.g. quinic or shikimic acid) are parts of hydrolysable tannins. Isomerism and nomenclature Unsubstituted cyclitols with the same ring size and number of hydroxyls may exist in several structural isomers, depending on the position of the hydroxyls along the ring. For example, cyclohexanetriol exists in three distinct isomers (1,2,3-, 1,2,4-, and 1,3,5-). Furthermore, the hydrogen and the h ...
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1,2,3,4-cyclohexanetetrol (generic)
1,2,3,4-Cyclohexanetetrol (also named cyclohexane-1,2,3,4-tetrol, 1,2,3,4-tetrahydroxycyclohexane, or ''ortho''-cyclohexanetetrol) is an organic compound whose molecule can be described as a cyclohexane with four hydroxyl (OH) groups substituted for hydrogen atoms on four consecutive carbon atoms. Its formula can be written , , or (––)4(––)2. There are 10 isomers with this same structural formula, which are among the 43 isomers of cyclohexanetetrol. They are all polyols, more specifically tetrols and cyclitols. Some of them have biologically important roles in some organisms. Isomers and nomenclature There are 10 different isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...s of this compound, that differ in the orientation of the four hydroxyls relative to the mean ...
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Inositol
Inositol, or more precisely ''myo''-inositol, is a carbocyclic sugar that is abundant in the brain and other mammalian tissues; it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation. It is a sugar alcohol with half the sweetness of sucrose (table sugar). It is made naturally in the human body from glucose. A human kidney makes about two grams per day. Other tissues synthesize it too, and the highest concentration is in the brain, where it plays an important role by making other neurotransmitters and some steroid hormones bind to their receptors. Inositol is promoted as a dietary supplement in the management of polycystic ovary syndrome (PCOS). However, there is only evidence of very low quality for its efficacy in increasing fertility for IVF in women with PCOS. Overview ''myo''-Inositol plays an important role as the structural basis for a number of secondary messengers in eukaryotic ...
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1,2,3,4-Cyclohexanetetrol
1,2,3,4-Cyclohexanetetrol (also named cyclohexane-1,2,3,4-tetrol, 1,2,3,4-tetrahydroxycyclohexane, or ''ortho''-cyclohexanetetrol) is an organic compound whose molecule can be described as a cyclohexane with four hydroxyl (OH) groups substituted for hydrogen atoms on four consecutive carbon atoms. Its formula can be written , , or (––)4(––)2. There are 10 isomers with this same structural formula, which are among the 43 isomers of cyclohexanetetrol. They are all polyols, more specifically tetrols and cyclitols. Some of them have biologically important roles in some organisms. Isomers and nomenclature There are 10 different isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...s of this compound, that differ in the orientation of the four hydroxyls relative to the mean ...
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Phytic Acid
Phytic acid is a six-fold dihydrogenphosphate ester of inositol (specifically, of the ''myo'' isomer), also called inositol hexakisphosphate (IP6) or inositol polyphosphate. At physiological pH, the phosphates are partially ionized, resulting in the phytate anion. The (''myo'') phytate anion is a colorless species that has significant nutritional role as the principal storage form of phosphorus in many plant tissues, especially bran and seeds. It is also present in many legumes, cereals, and grains. Phytic acid and phytate have a strong binding affinity to the dietary minerals, calcium, iron, and zinc, inhibiting their absorption in the small intestine. The lower inositol polyphosphates are inositol esters with less than six phosphates, such as inositol penta- (IP5), tetra- (IP4), and triphosphate (IP3). These occur in nature as catabolites of phytic acid. Significance in agriculture Phytic acid was discovered in 1903. Generally, phosphorus and inositol in phytate form ...
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Ciceritol
Ciceritol is a cyclitol. It is a pinitol digalactoside that can be isolated from seeds of chickpea, lentil and white lupin ''Lupinus albus'', commonly known as the white lupin or field lupine, is a member of the genus ''Lupinus'' in the family Fabaceae. It is a traditional pulse cultivated in the Mediterranean region. Description The white lupin is annual, more .... References Cyclitols Galactosides {{organic-compound-stub ...
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Viscumitol
Viscumitol is a cyclitol. It is a dimethyl-ether of ''muco''-inositol that can be isolated from ''Viscum album ''Viscum album'' is a species of mistletoe in the family Santalaceae, commonly known as European mistletoe, common mistletoe or simply as mistletoe (Old English ''mistle''). It is native to Europe and western and southern Asia. ''Viscum album'' ...''. References Cyclitols Methoxy compounds {{organic-compound-stub ...
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Valienol
Valienol (streptol) is a C-7 cyclitol similar in structure to valienamine Valienamine is a C-7 aminocyclitol found as a substructure of pseudooligosaccharides such as the antidiabetic drug acarbose and the antibiotic validamycin. It can be found in ''Actinoplanes ''Actinoplanes'' is a genus in the family Micromono .... References Cyclitols Cyclohexenes {{Alcohol-stub ...
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Shikimic Acid
Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower ''shikimi'' (, the Japanese star anise, ''Illicium anisatum''), from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later. Biosynthesis Phosphoenolpyruvate and erythrose-4-phosphate condense to form 3-deoxy-D-arabinoheptulosonate-7-phosphate (DAHP), in a reaction catalyzed by the enzyme DAHP synthase. DAHP is then transformed to 3-dehydroquinate (DHQ), in a reaction catalyzed by DHQ synthase. Although this reaction requires nicotinamide adenine dinucleotide (NAD) as a cofactor, the enzymic mechanism regenerates it, resulting in the net use of no NAD. : DHQ is dehydrated to 3-dehydroshikimic acid by the enzyme 3-dehydroquinate dehydratase, which is reduced to shiki ...
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Quinic Acid
Quinic acid is a cyclitol, a cyclic polyol, and a cyclohexanecarboxylic acid. It is a colorless solid that can be extracted from plant sources. Quinic acid is implicated in the perceived acidity of coffee. Occurrence and preparation The compound is obtained from cinchona bark, coffee beans, and the bark of ''Eucalyptus globulus''. It is a constituent of the tara tannins. ''Urtica dioica'' is another common source. It is made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee. History and biosynthesis This substance was isolated for the first time in 1790 by German pharmacist Friedrich Christian Hofmann in Leer from Cinchona. Its transformation into hippuric acid by animal metabolism was studied by German chemist Eduard Lautemann in 1863.Lautemann, E. (1863"Ueber die Reduction der Chinasäure zu Benzoësäure und die Verwandlung derselben in Hippursäure im thierischen Organismus"(On the reduction of quinic ...
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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 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 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, ...
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Pinpollitol
Pinpollitol is a cyclitol. It is a di-''O''-methyl-(+)- chiro-inositol that can be isolated from ''Pinus radiata ''Pinus radiata'' ( syn. ''Pinus insignis''), the Monterey pine, insignis pine or radiata pine, is a species of pine native to the Central Coast of California and Mexico (Guadalupe Island and Cedros island). It is an evergreen conifer in the fa ...''. References Cyclitols {{organic-compound-stub ...
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Ononitol
Ononitol is a cyclitol. It is a 4-''O''-methyl-myo-inositol and is a constituent of ''Medicago sativa Alfalfa () (''Medicago sativa''), also called lucerne, is a perennial flowering plant in the legume family Fabaceae. It is cultivated as an important forage crop in many countries around the world. It is used for grazing, hay, and silage, as we ...''. References Cyclitols {{organic-compound-stub ...
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