Inositol
| Names | |
|---|---|
| IUPAC name
myo-Inositol | |
| Systematic IUPAC name
(1R,2S,3r,4R,5S,6s)-Cyclohexane-1,2,3,4,5,6-hexol | |
| Other names
cis-1,2,3,5-trans-4,6-Cyclohexanehexol Cyclohexanehexol Mouse antialopecia factor Nucite Phaseomannite Phaseomannitol Rat antispectacled eye factor Scyllite (for the isomer scyllo-inositol) Vitamin B8 | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.027.295 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H12O6 | |
| Molar mass | 180.16 g/mol |
| Density | 1.752 g/cm3 |
| Melting point | 225 to 227 °C (437 to 441 °F; 498 to 500 K) |
| Thermochemistry | |
Std enthalpy of formation (ΔfH⦵298) |
−1329.3 kJ/mol |
Std enthalpy of combustion (ΔcH⦵298) |
−2747 kJ/mol |
| Pharmacology | |
| A11HA07 (WHO) | |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 143 °C (289 °F; 416 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
In biochemistry, medicine, and related sciences, inositol generally refers to myo-inositol (formerly meso-inositol), the most important stereoisomer of the chemical compound cyclohexane-1,2,3,4,5,6-hexol. Its formula is C6H12O6; the molecule has a ring of six carbon atoms, each with a hydrogen atom and a hydroxyl group (–OH). In myo-inositol, two of the hydroxyls, neither adjacent nor opposite, lie above the respective hydrogens relative to the mean plane of the ring.
The compound is a carbohydrate, specifically a sugar alcohol (as distinct from aldoses like glucose) with half the sweetness of sucrose (table sugar). It is one of the most ancient components of living beings with multiple functions in eukaryotes, including structural lipids and secondary messengers. A human kidney makes about two grams per day from glucose, but other tissues synthesize it too. The highest concentration is in the brain, where it plays an important role in making other neurotransmitters and some steroid hormones bind to their receptors. In other tissues, it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation. In most mammalian cells the concentrations of myo-inositol are 5 to 500 times greater inside cells than outside them.
A 2023 meta-analysis found that inositol is a safe and effective treatment 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.
The other naturally occurring stereoisomers of cyclohexane-1,2,3,4,5,6-hexol are scyllo-, muco-, D-chiro-, L-chiro-, and neo-inositol, although they occur in minimal quantities compared to myo-inositol. The other possible isomers are allo-, epi-, and cis-inositol.