Common NameScyllo-inositol
Descriptionscyllo-Inositol or scyllitol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol. scyllo-Inositol was first isolated from the kidneys of fish in 1858 by Staedeler and Freierchs. scyllo-Inositol is a naturally occurring plant sugar alcohol found most abundantly in the coconut palm. It appears to accumulate in a number of human tissues and biofluids through dietary consumption. It has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379). Results reported by Viola et al (PMID: 15340856 ) suggest that high CSF concentrations of scyllo-inositol can be induced by chronic alcoholism. scyllo-Inositol when fed to transgenic mice that exhibit a memory disease very similar to human Alzheimer's disease, can block the accumulation of soluble amyloid-beta (Aβ) plaques in the brain. scyllo-Inositol was found to reverse memory deficits in the mice, reduce the amount of Aβ plaque in the brains of the mice, and reversed other symptoms associated with the presence of Aβ in the brain (PMID: 16767098 ).
Structure
Molecular FormulaC6H12O6
Average Mass180.15590
Monoisotopic Mass180.06339
IUPAC Name(1R,2S,3r,4R,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol
Traditional NameInositol
CAS Registry Number488-59-5
SMILESO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3+,4+,5-,6-
InChI KeyCDAISMWEOUEBRE-CDRYSYESSA-N
CHEBI IDCHEBI:10642
HMDB IDHMDB0006088
StateSolid
Water Solubility4.85e+02 g/l
logP-2.59
logS0.43
pKa (Strongest Acidic)12.29
pKa (Strongest Basic)-3.65
Hydrogen Acceptor Count6
Hydrogen Donor Count6
Polar Surface Area121.38 Ų
Rotatable Bond Count0
Physiological Charge0
Formal Charge0
Refractivity35.78 m³·mol⁻¹
Polarizability16.05

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