1.0 2010-04-08 22:04:51 UTC 2025-11-18 22:28:23 UTC FDB001138 Chiro-Inositol Levoinositol (also known as 1L-chiro-Inositol or L-chiro-inositol, abbreviated LCI) is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, with the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol. In humans, most inositol is synthesized in the kidneys, typically in amounts of a few grams per day. Levoinositol is found in dandelion and is widely distributed in higher plants predominantly as its monomethyl ether. It is found in many foods, particularly in cereals with high bran content. It is an isomer of glucose that has traditionally been a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in humans. Inositol is a cyclic polyalcohol that plays an important role as a second messenger in a cell, in the form of inositol phosphates. Inositol phospholipids are important in signal transduction. A possible health effect of inositols, including chiro-inositol, was recently reviewed. The review concluded that myo-inositol, together with chiro-inositol, at a 40:1 ratio, were an important therapeutic strategy for the improvement of metabolic, hormonal, and reproductive aspects of polycystic ovarian syndrome (PMID: 29309199). (1a,2a,3b,4a,5b,6b)-Cyclohexanehexol 1,2,4/3,5,6-Inositol Chiroinositol C6H12O6 180.1559 180.063388116 (1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol D-chiro-inositol 643-12-9 O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m0/s1 CDAISMWEOUEBRE-LKPKBOIGSA-N belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Cyclohexanols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homomonocyclic compounds Cyclitols and derivatives Hydrocarbon derivatives Polyols Sugar alcohols Aliphatic homomonocyclic compound Cyclic alcohol Cyclitol or derivatives Cyclohexanol Hydrocarbon derivative Polyol Sugar alcohol chiro-inositol logp -2.59 ALOGPS logs 0.43 ALOGPS solubility 4.85e+02 g/l ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 12.29 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol ChemAxon average_mass 180.1559 ChemAxon mono_mass 180.063388116 ChemAxon smiles O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C6H12O6 ChemAxon 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+/m0/s1 ChemAxon inchikey CDAISMWEOUEBRE-LKPKBOIGSA-N ChemAxon polar_surface_area 121.38 ChemAxon refractivity 35.78 ChemAxon polarizability 16.1 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14892 Specdb::CMs 43770 Specdb::CMs 151341 Specdb::MsMs 45072 Specdb::MsMs 45073 Specdb::MsMs 45074 Specdb::MsMs 140445 Specdb::MsMs 140446 Specdb::MsMs 140447 Specdb::MsMs 2422866 Specdb::MsMs 2422867 Specdb::MsMs 2422868 Specdb::MsMs 2513153 Specdb::MsMs 2513154 Specdb::MsMs 2513155 Specdb::NmrOneD 72092 Specdb::NmrOneD 72093 Specdb::NmrOneD 72094 Specdb::NmrOneD 72095 Specdb::NmrOneD 72096 Specdb::NmrOneD 72097 Specdb::NmrOneD 72098 Specdb::NmrOneD 72099 Specdb::NmrOneD 72100 Specdb::NmrOneD 72101 Specdb::NmrOneD 72102 Specdb::NmrOneD 72103 Specdb::NmrOneD 72104 Specdb::NmrOneD 72105 Specdb::NmrOneD 72106 Specdb::NmrOneD 72107 Specdb::NmrOneD 72108 Specdb::NmrOneD 72109 Specdb::NmrOneD 72110 Specdb::NmrOneD 72111 HMDB0034220 Carob Type 1 specific Ceratonia siliqua 20340 100.0 100.0 100.0 mg/100 g Soy bean Type 1 specific Glycine max 3847