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1L-chiro-Inositol

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1L-chiro-Inositol
Names
IUPAC name 1L-chiro-Inositol
Systematic IUPAC name (1R,2R,3R,4R,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.183 Edit this at Wikidata
UNII
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+/m1/s1Key: CDAISMWEOUEBRE-SHFUYGGZSA-N
SMILES
  • O1(O)(O)(O)(O)1O
Properties
Chemical formula C6H12O6
Molar mass 180.156 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

1L-chiro-Inositol (L-chiro-Inositol) is one of the nine stereoisomers of the chemical compound cyclohexane-1,2,3,4,5,6-hexol, with formula C6H12O6, often called "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.

Laboratory synthesis

Structure

L-chiro-inositol crystallizes in the monoclinic system, group P21, with cell dimensions a = 686.7 pm, b = 913.3 pm, c = 621.7 pm (±0.004 pm) angle β = 106.59° (± 0.04°), molecular count Z = 2. The molecule has the expected chair conformation, with puckering parameters Q = 56.1 pm, θ = 4.4°, φ = 51.2°. The non-hydrogen molecular symmetry is close to C2. The C–C bond lengths range from 151.5 to 152.8 pm, and the C–O bond lengths from 141.8 to 143.6 pm. The C–C–C angles range from 109.7 to 113.1°, and the C–C–O angles from 106.5 to 112.0°.

See also

References

  1. ^ IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-104.2.1". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
  2. George A. Jeffrey, Younghee Yeon (1987): "The crystal structure of l-chiro-inositol". Carbohydrate Research, volume 159, issue 2, pages 211-216. doi:10.1016/S0008-6215(00)90216-7


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