Neo-Inositol

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.

neo-Inositol

Names
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
CAS Number	488-54-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:25492 Y
ChemSpider	10199749 Y
UNII	8LQ63P85IC Y
InChI InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5-,6- Y Key: CDAISMWEOUEBRE-DCLYFUHFSA-N Y
SMILES O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@H](O)[C@H]1O
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

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 ${\displaystyle P{\bar {1}}}$. 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 ${\displaystyle {\bar {1}}}$. 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]

See also

• allo-Inositol
• cis-Inositol
• D-chiro-Inositol
• L-chiro-Inositol
• epi-Inositol
• muco-Inositol
• scyllo-Inositol