chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
1L-''chiro''-inositol (often called L-''chiro''-inositol or LCI) is one of the nine
stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
s of
cyclohexane-1,2,3,4,5,6-hexol
Cyclohexane-1,2,3,4,5,6-hexol is a family of chemical compounds with elemental formula, formula , 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 ...
, with formula , the generic "
inositol
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 elemental formula, formula is ...
". Its molecule has a ring of six
carbon
Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
atoms, each bonded to a
hydrogen
Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...
atom and a
hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
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.
The compound occurs in the human body and other organisms, together with its
enantiomer
In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...
monoclinic
In crystallography, the monoclinic crystal system is one of the seven crystal systems. A crystal system is described by three Vector (geometric), vectors. In the monoclinic system, the crystal is described by vectors of unequal lengths, as in t ...
system,
group
A group is a number of persons or things that are located, gathered, or classed together.
Groups of people
* Cultural group, a group whose members share the same cultural identity
* Ethnic group, a group whose members share the same ethnic iden ...
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
Cyclohexane conformations are any of several three-dimensional shapes adopted by cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane are important prototypes of a wide r ...
, 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°.
Laboratory synthesis
L-''chiro''-inositol can be prepared from ''myo''-inositol. It can be prepared also from ''para''-benzoquinone by
enzymatic
An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as produc ...
action on a derived conduritol B intermediate; or by controlled oxidation of cyclohexa-3,5-diene-1,2-diol.
Another viable method is decomposition of plant-sourced
quebrachitol
Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. It can be found in '' Allophylus edulis'' and in the serum left after the coagulation of the ''Hevea brasiliensis'' latex in the operation of rubber tapping. It is a ...
, which can be obtained in good quantity from natural rubber serum (NRS), the liquid remaining from coagulation of
latex
Latex is an emulsion (stable dispersion) of polymer microparticles in water. Latices are found in nature, but synthetic latices are common as well.
In nature, latex is found as a wikt:milky, milky fluid, which is present in 10% of all floweri ...
from ''
Hevea brasiliensis
''Hevea brasiliensis'', the Pará rubber tree, ''sharinga'' tree, seringueira, or most commonly, rubber tree or rubber plant, is a flowering plant belonging to the spurge family, Euphorbiaceae, originally native to the Amazon basin, but is now p ...
''.
Natural occurrence
L-''chiro''-inositol occurs, together with the D- isomer, in
phospholipids
Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids typi ...
of animal tissues. Analysis of rat tissues shows predominance of DCI in fat, liver, brain and kidney, and approximately equal amounts of DCI and LCI in muscles. L-chiro-inositol is also found in plants and parasites as
quebrachitol
Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. It can be found in '' Allophylus edulis'' and in the serum left after the coagulation of the ''Hevea brasiliensis'' latex in the operation of rubber tapping. It is a ...
, an
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
of LCI — specifically, 2-O-methyl-L-''chiro''-inositol.
L-''chiro''-inositol can be extracted from dead leaf material from the seagrass ''
Syringodium filiforme
''Syringodium filiforme'', commonly known as manatee grass, is a species of marine seagrass. It forms meadows in shallow sandy or muddy locations in the Caribbean Sea and the Gulf of Mexico, and is also found in the Bahamas and Bermuda. It occur ...
'' that washes up as flotsam on Caribbean beaches. Yeld of 2.3–2.5% of dry weight has been reported.
Microbial action in soil incubated for 12 days at 70% moisture converted about 4% of the at converted about 4% of infused ''myo''-inositol to ''chiro''-inositol of unspecified (D or L) optical activity.
George A. Jeffrey, Younghee Yeon (1987): "The crystal structure of l-chiro-inositol". ''Carbohydrate Research'', volume 159, issue 2, pages 211-216. 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. M. Belén Cid, Francisco Alfonso, Manuel Martín-Lomas (2003): "L-''chiro''-inositol derivatives from ''myo''-inositol. Building blocks for inositol phosphoglycans". ''Synlett'', volume 2003, issue 9, pages 1370-1372. Larry E Brammer Jr., Tomas Hudlicky (1998): "Inositol synthesis: concise preparation of l-chiro-inositol and muco-inositol from a common intermediate". ''Tetrahedron: Asymmetry'', volume 9, issue 12, 19 june , pages 2011-2014 Christine Sue Chen Lee, Manroshan Singh, Chin-Hoe Teh, Dazylah Darji, Azhar Ahmad & Zairossani Mohd Nor (2023): "Modification of quebrachitol extracted from natural rubber serum (NRS) to L-''chiro''-inositol for pharmaceutical and nutraceutical applications". ''Journal of Rubber Research'', volume 26, pages 179–192 Gladys Nuissier a, Faïza Diaba b, Micheline Grignon-Dubois a (2008): "Bioactive agents from beach waste: ''Syringodium'' flotsam evaluation as a new source of L-''chiro''-inositol". ''Innovative Food Science & Emerging Technologies'', volume 9, issue 3, pages 396-400. Michael F. L'Annunziata, Juan González Iturbe, Luis A. Olivares Orozco (1977) "Microbial epimerization of ''myo''-inositol to ''chiro''-inositol in soil". ''Soil Science Society of America Journal'', Division S-3 - ''Soil Microbiology and Biochemistry'', volume 41, issue 4, pages 733-736. Sigma-Aldrich (2024), Product 468053: L-(−)-chiro-Inositol . Online catalog, accessed on 2024-06-31.Joseph Larner (2000): "D-chiro-inositol – Its functional role in insulin action and its deficit in insulin resistance". ''Journal of Diabetes Research'', volume 3, pages 47-60. Howard A. J. Carless, K. Busia, O. Z. Oak (1993): "Microbial oxidation of benzene as a route to inositol stereoisomers and (±)-quebrachitol". ''Synlett'', volume 1993, issue 9, pages 672-674.
{{DEFAULTSORT:Inositol, L-chiro-
Inositol