Neo-Inositol
Chemical compound
From Wikipedia, the free encyclopedia
The chemical compound neo-inositol is one of the nine stereoisomers cyclohexane-1,2,3,4,5,6-hexol, the "inositols". Its formula is C6H12O6; the six carbon atoms form a ring, each of them is bonded to a hydrogen atom and a hydroxyl group (–OH). If the ring is assumed horizontal, three consecutive hydroxyls lie above the respective hydrogens, and the other three lie below them.
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| Names | |
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| IUPAC name
neo-Inositol[1] | |
| Systematic IUPAC name
(1R,2R,3s,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol | |
| Other names
(1s,2R,3R,4s,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol;
1,2,3/4,5,6-cyclohexanehexol[2] | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| UNII | |
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| Properties | |
| C6H12O6 | |
| Molar mass | 180.156 g·mol−1 |
| Appearance | white crystalline solid [3] |
| Density | 1.697 g/ml (from X-ray structure)[4] |
| Melting point | 315 °C; 599 °F; 588 K[5][6] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Irritating to eyes, respiratory system and skin.[7] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Like the other stereoisomers, neo-inositol is considered a carbohydrate, specifically a sugar alcohol (to distinguish it from the more familiar ketose and aldose sugars, like glucose). It occurs in nature, but only in small amounts; usually much smaller than those of myo-inositol, the most important stereoisomer.[8]
Chemical and physical properties
Crystal structure
neo-inositol crystallizes in the triclinic system with group . The cell parameters are a = 479.9 pm, b = 652.0 pm, c = 650.5 pm, α = 70.61°, β = 69.41°, γ = 73.66°, Z = 1, with molecular symmetry . The cell volume is 0.176 nm3. The ring has the chair conformation with puckering parameter Q = 60.9 pm.[4]
Synthesis
neo-Inositol can be obtained from para-benzoquinone via conduritol intermediates.[9]
Natural occurrence and biological roles
Small amounts of neo-inositol can be deteceted in human urine.[10]
