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.

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.

Crystal structure
neo-inositol crystallizes in the triclinic system with group $$P\bar 1$$. 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 $$\bar 1$$. The cell volume is 0.176 nm3. The ring has the chair conformation with puckering parameter Q = 60.9 pm.

Synthesis
neo-Inositol can be obtained from para-benzoquinone via conduritol intermediates.

Natural occurrence and biological roles
Small amounts of neo-inositol can be deteceted in human urine.