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Inositol

myo-Inositol[1]
myo-Inositol
myo-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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.027.295 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6- checkY
    Key: CDAISMWEOUEBRE-GPIVLXJGSA-N checkY
  • InChI=1/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-
    Key: CDAISMWEOUEBRE-GPIVLXJGBG
  • O[C@@H]1[C@@H](O)[C@H](O)[C@H](O)[C@H](O)[C@H]1O
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[2]
−1329.3 kJ/mol
−2747 kJ/mol
Pharmacology
A11HA07 (WHO)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
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).
checkY verify (what is checkY☒N ?)

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 an hydrogen atom and a hydroxyl group (–OH). In myo-inositol, two of the hydroxyls, neither adjacent not 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.[3] 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.[4] In other tissues, it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation.[5] In most mammalian cells the concentrations of myo-inositol are 5 to 500 times greater inside cells than outside them.[6]

A 2023 meta-analysis found that inositol is a safe and effective treatment in the management of polycystic ovary syndrome (PCOS).[7] However, there is only evidence of very low quality for its efficacy in increasing fertility for IVF in women with PCOS.[8]

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.

  1. ^ Merck Index (11th ed.). p. 4883.
  2. ^ Knyazev, A.V.; Emel’yanenko, V.N.; Shipilova, A.S.; Zaitsau, D.H.; Lelet, M.I.; Knyazeva, S.S.; Gusarova, E.V.; Varfolomeev, M.A. (2018). "Thermodynamic properties of myo-inositol". The Journal of Chemical Thermodynamics. 116: 76–84. doi:10.1016/j.jct.2017.08.028. ISSN 0021-9614.
  3. ^ Cite error: The named reference liyu2021 was invoked but never defined (see the help page).
  4. ^ Croze, M. L.; Soulage, C. O. (October 2013). "Potential role and therapeutic interests of myo-inositol in metabolic diseases". Biochimie. 95 (10): 1811–1827. doi:10.1016/j.biochi.2013.05.011. PMID 23764390.
  5. ^ Parthasarathy, L. K.; Seelan, R. S.; Tobias, C.; Casanova, M. F.; Parthasarathy, R. N. (2006). Mammalian inositol 3-phosphate synthase: its role in the biosynthesis of brain inositol and its clinical use as a psychoactive agent. Subcellular Biochemistry. Vol. 39. pp. 293–314. doi:10.1007/0-387-27600-9_12. ISBN 978-0-387-27599-4. PMID 17121280.
  6. ^ Cite error: The named reference pmid33755975 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference pcos2023 was invoked but never defined (see the help page).
  8. ^ Showell, M. G.; Mackenzie-Proctor, R.; Jordan, V.; Hodgson, R.; Farquhar, C. (2018). "Inositol for subfertile women with polycystic ovary syndrome". The Cochrane Database of Systematic Reviews. 2018 (12): CD012378. doi:10.1002/14651858.CD012378.pub2. PMC 6516980. PMID 30570133.

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