1D-chiro-Inositol

1D-chiro-Inositol

Names
IUPAC name 1D-chiro-Inositol
Systematic IUPAC name (1R,2R,3S,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexol
Other names DCI cis-1,2,4-trans-3,5,6-Cyclohexanehexol 1D-1,2,4/3,5,6-Cyclohexanehexol 1,2,4/3,5,6-Hexahydroxycyclohexane (+)-inositol
Identifiers
CAS Number	643-12-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27372 Y
ChemSpider	10254647 Y
ECHA InfoCard	100.010.359
IUPHAR/BPS	4645
UNII	6R79WV4R10 Y
CompTox Dashboard (EPA)	DTXSID60903982
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 Y Key: CDAISMWEOUEBRE-LKPKBOIGSA-N Y
SMILES O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Properties
Chemical formula	C6H12O6
Molar mass	180.156 g·mol−1
Melting point	230 °C (446 °F; 503 K)
Chiral rotation ([α]D)	[α]23/D +55°, c = 1.2 in H2O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

1D-chiro-Inositol (formerly D-chiro-inositol, commonly abbreviated DCI) is a member of a family of related substances often referred to collectively as "inositol", although that term encompasses several isomers of questionable biological relevance, including 1L-chiro-inositol. myo-Inositol is converted into DCI by an insulin dependent NAD/NADH epimerase enzyme. It is known to be an important secondary messenger in insulin signal transduction. DCI accelerates the dephosphorylation of glycogen synthase and pyruvate dehydrogenase, rate limiting enzymes of non-oxidative and oxidative glucose disposal. DCI may act to bypass defective normal epimerization of myo-inositol to DCI associated with insulin resistance and at least partially restore insulin sensitivity and glucose disposal. One pilot study found males taking it had increased androgens and reduced estrogen.