Neo-Inositol

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neo-Inositol
Neo-inositol.svg
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
3D model (JSmol)
ChEBI
ChemSpider
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- Yes check.svgY
    Key: CDAISMWEOUEBRE-DCLYFUHFSA-N Yes check.svgY
  • O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@H](O)[C@H]1O
Properties
C6H12O6
Molar mass 180.156 g·mol−1
Appearancewhite 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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 nm 3. 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

Related Research Articles

Inositol trisphosphate or inositol 1,4,5-trisphosphate abbreviated InsP3 or Ins3P or IP3 is an inositol phosphate signaling molecule. It is made by hydrolysis of phosphatidylinositol 4,5-bisphosphate (PIP2), a phospholipid that is located in the plasma membrane, by phospholipase C (PLC). Together with diacylglycerol (DAG), IP3 is a second messenger molecule used in signal transduction in biological cells. While DAG stays inside the membrane, IP3 is soluble and diffuses through the cell, where it binds to its receptor, which is a calcium channel located in the endoplasmic reticulum. When IP3 binds its receptor, calcium is released into the cytosol, thereby activating various calcium regulated intracellular signals.

<span class="mw-page-title-main">Hexose</span> 6-Carbon simple sugar

In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol.

<span class="mw-page-title-main">Inositol</span> Carbocyclic sugar

In biochemistry, medicine, and related sciences, inositol generally refers to myo-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.

<span class="mw-page-title-main">Phosphatidylinositol</span> Signaling molecule

Phosphatidylinositol or inositol phospholipid is a biomolecule. It was initially called "inosite" when it was discovered by Léon Maquenne and Johann Joseph von Scherer in the late 19th century. It was discovered in bacteria but later also found in eukaryotes, and was found to be a signaling molecule.

The molecular formula C6H12O6 (molar mass: 180.16 g/mol) may refer to:

<span class="mw-page-title-main">Inositol oxygenase</span> Protein-coding gene in the species Homo sapiens

Inositol oxygenase, also commonly referred to as myo-inositol oxygenase (MIOX), is a non-heme di-iron enzyme that oxidizes myo-inositol to glucuronic acid. The enzyme employs a unique four-electron transfer at its Fe(II)/Fe(III) coordination sites and the reaction proceeds through the direct binding of myo-inositol followed by attack of the iron center by diatomic oxygen. This enzyme is part of the only known pathway for the catabolism of inositol in humans and is expressed primarily in the kidneys. Recent medical research regarding MIOX has focused on understanding its role in metabolic and kidney diseases such as diabetes, obesity and acute kidney injury. Industrially-focused engineering efforts are centered on improving MIOX activity in order to produce glucaric acid in heterologous hosts.

1<small>D</small>-<i>chiro</i>-Inositol Chemical compound

1D-chiro-Inositol or D-chiro-inositol is a chemical substance with formula C6H12O6, one of the nine isomers of cyclohexane-1,2,3,4,5,6-hexol. The molecule has a ring of six carbon atoms, each bound to one hydrogen atom and one hydroxyl (OH) group. The hydroxyls on atoms 1, 2, and 4, in counterclockwise order, lie above the plane of the ring. The molecule being distinct from its mirror image, the compound is chiral, hence its name. Its enantiomer is 1L-chiro-inositol.

<i>scyllo</i>-Inositol Chemical compound

scyllo-Inositol, also called scyllitol, cocositol, or quercinitol, is a chemical compound with formula C6H12O6, one of the nine inositols, the stereoisomers of cyclohexane-1,2,3,4,5,6-hexol. The molecule has a ring of six carbon atoms, each bound to one hydrogen atom and one hydroxyl group (–OH); if the ring is assumed horizontal, the hydroxyls lie alternatively above and below the respective hydrogens.

<span class="mw-page-title-main">Inositol-phosphate phosphatase</span> Class of enzymes

The enzyme Inositol phosphate-phosphatase is of the phosphodiesterase family of enzymes. It is involved in the phosphophatidylinositol signaling pathway, which affects a wide array of cell functions, including but not limited to, cell growth, apoptosis, secretion, and information processing. Inhibition of inositol monophosphatase may be key in the action of lithium in treating bipolar disorder, specifically manic depression.

<span class="mw-page-title-main">Isomer</span> Chemical compounds with the same molecular formula but different atomic arrangements

In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element – but distinct arrangements of atoms in space. Diamond and graphite are a familiar example; they are isomers of carbon. Isomerism refers to the existence or possibility of isomers.

<span class="mw-page-title-main">Tetrahydroxy-1,4-benzoquinone</span> Chemical compound

Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-p-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone, is an organic compound with formula C6O2(OH)4. Its molecular structure consists of a cyclohexadiene ring with four hydroxyl groups and two ketone groups in opposite (para) positions.

<i>muco</i>-Inositol Chemical compound

muco-Inositol is a critically important chemical in the gustatory (taste) modality of the mammalian nervous system. The generic form is coupled to a phospholipid of the outer lemma of the sensory neurons associated with the sodium ion sensitive channel of gustation.

1<small>L</small>-<i>chiro</i>-Inositol Chemical compound

The chemical compound 1L-chiro-inositol is one of the nine stereoisomers of cyclohexane-1,2,3,4,5,6-hexol, with formula C6H12O6, the generic "inositol". Its molecule has a ring of six carbon atoms, each bonded to a hydrogen atom and a hydroxyl group (–OH). Imagining the ring is horizontal, the hydroxyls on carbons 1, 2, and 4, in clockwise order are above the respective hydrogens, while the other three are below them.

<i>epi</i>-Inositol Chemical compound

Epi-Inositol is one of the stereoisomers of inositol.

<i>cis</i>-Inositol Chemical compound

cis-Inositol is one of the isomers of inositol.

<i>allo</i>-Inositol Chemical compound

allo-Inositol is a stereoisomer of inositol.

<span class="mw-page-title-main">Cyclitol</span> Class of chemical compounds

In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is C
nH
2n-x(OH)
x or C
nH
2nO
x where 3 ≤ x ≤ n.

2,5-Dihydroxy-1,4-benzoquinone or 2,5-dihydroxy-para-benzoquinone is an organic compound with formula C
6H
4O
4, formally derived from 1,4-benzoquinone by replacing two hydrogen atoms with hydroxyl (OH) groups. It is one of seven dihydroxybenzoquinone isomers. It is a yellow solid with planar molecules that exhibits ferroelectric properties.

<span class="mw-page-title-main">1,2,3,4,5-Cyclopentanepentol</span> Chemical compound

1,2,3,4,5-Cyclopentanepentol, also named cyclopentane-1,2,3,4,5-pentol or 1,2,3,4,5-pentahydroxycyclopentane is a chemical compound with formula C
5H
10O
5 or (–CHOH–)
5, whose molecule consists of a ring of five carbon atoms, each connected to one hydrogen and one hydroxyl group. The unqualified term "cyclopentanepentol" usually refers to this compound. There are four distinct stereoisomers with this same structure.

<span class="mw-page-title-main">Cyclohexane-1,2,3,4,5,6-hexol</span> Family of sugars with a six-carbon ring

Cyclohexane-1,2,3,4,5,6-hexol is a family of chemical compounds with formula C6H12O6, whose molecule consists of a ring of six carbon atoms, each bound to one hydrogen atom and one hydroxyl group (–OH). There are nine stereoisomers, that differ by the position of the hydroxyl groups relative to the mean plane of the ring. All these compounds are sometimes called inositol, although this name most often refers to a particular isomer, myo-inositol, which has many important physiological roles and medical uses.

References

  1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1415. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. ↑ "Neo-Inositol" . Retrieved 9 October 2012.
  3. ↑ Synthose Inc. (2024): "". Product catalog page at [synthose.com]. Accessed on 2024-07-02.
  4. 1 2 Younghee Yeon (2001): "The crystal and molecular structures of neo-inositol and two forms of scyllo-inositol". Korean Journal of Crystallography, volume 12, issue 3, pages 150-156.
  5. ↑ Alexandra Simperler, Stephen W. Watt, P. Arnaud Bonnet, William Jones, W. D. Samuel Motherwell (2006): "Correlation of melting points of inositols with hydrogen bonding patterns". CrystEngComm, volume 8, pages 589-600 doi : 10.1039/B606107A
  6. ↑ Watt, S. W.; Chisholm, J. A.; Jones, W.; Motherwell, S. (2004). "A Molecular Dynamics Simulation of the Melting Points and Glass Transition Temperatures of Myo- and Neo-Inositol". Journal of Chemical Physics. 121 (19): 9565–9573. doi:10.1063/1.1806792. PMID   15538878.
  7. ↑ "Material Safety Data Sheet". Sigma-Aldrich. Retrieved 9 October 2012.
  8. ↑ Michell, R. H. (February 2008). "Inositol Derivatives: Evolution and Functions" (PDF). Nature Reviews Molecular Cell Biology. 9 (2): 151–61. doi:10.1038/nrm2334. PMID   18216771.
  9. ↑ Michael Podeschwa, Oliver Plettenburg, Jochen vom Brocke, Oliver Block, Stephan Adelt, Hans-Josef Altenbach (2003): "Stereoselective synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-inositol systems via conduritols prepared from p-benzoquinone". European Journal of Organic Chemistry, volume 2003, issue 10, pages 1958-1972. doi : 10.1002/ejoc.200200572
  10. ↑ Irina Monnard, Thierry Bénet, Rosemarie Jenni, Sean Austin, Irma Silva-Zolezzi, Jean-Philippe Godin (2020): "Plasma and urinary inositol isomer profiles measured by UHPLC-MS/MS reveal differences in scyllo-inositol levels between non-pregnant and pregnant women". Analytical and Bioanalytical Chemistry, volume 412, pages 7871–7880. doi : 10.1007/s00216-020-02919-8


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