# 1D-chiro-Inositol

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1D-chiro-Inositol[1] D-chiro-Inositol Names IUPAC name 1D-chiro-Inositol[2] 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[2] 1,2,4/3,5,6-Hexahydroxycyclohexane (+)-inositol[2] 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

Chemical compound

**1D-*chiro*-Inositol**[2] or **D-*chiro*-inositol**[3] (often abbreviated **DCI**) is a [chemical substance](/source/Chemical_substance) with formula C6H12O6, one of the nine [isomers](/source/Isomer) of [cyclohexane-1,2,3,4,5,6-hexol](/source/Cyclohexane-1%2C2%2C3%2C4%2C5%2C6-hexol) (which may be collectively called "inositol"). The molecule has a ring of six [carbon](/source/Carbon) atoms, each bound to one [hydrogen](/source/Hydrogen) atom and one [hydroxyl](/source/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](/source/Chirality_(chemistry)), hence its name. Its [enantiomer](/source/Enantiomer) (mirror compound) is [1L-*chiro*-inositol](/source/1L-chiro-inositol).

Compared to its more common isomer [*myo*-inositol](/source/Inositol), DCI seems to have relatively minor roles in [biochemistry](/source/Biochemistry) and medicine, mostly connected to the biochemistry of [insulin](/source/Insulin) and other [hormones](/source/Hormone).[4][5]

## Biochemistry and physiology

### Occurrence

The common isomer *myo*-inositol is converted into DCI in the human body by an [insulin](/source/Insulin) dependent [enzyme](/source/Enzyme), [NAD/NADH epimerase](https://en.wikipedia.org/w/index.php?title=NAD/NADH_epimerase&action=edit&redlink=1).[6][7][8][9][10]

### Insulin interactions

D-*chiro*-inositol is known to be an important [secondary messenger](/source/Secondary_messenger) in [insulin](/source/Insulin) [signal transduction](/source/Signal_transduction). It accelerates the dephosphorylation of glycogen synthase and pyruvate dehydrogenase, rate limiting enzymes of non-oxidative and oxidative glucose disposal. Exogenous 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.[4] In clinical practice, it improves insulin signaling, thus restoring physiological insulin levels in resistant subjects.[3]

### Hormonal treatment

D-*chiro*-inositol has been used to induce ovulation in women with polycystic ovary syndrome.[3]

DCI depresses the expression of the [steroidogenic enzyme](/source/Steroidogenic_enzyme) [aromatase](/source/Aromatase), which is responsible for the conversion of [androgens](/source/Androgens) to [estrogens](/source/Estrogens).[3] One pilot study found males taking DCI had increased androgens and reduced estrogen.[5]

## References

1. **[^](#cite_ref-1)** *[Merck Index](/source/Merck_Index)*, 11th Edition, **4883**

1. ^ [***a***](#cite_ref-bb_2-0) [***b***](#cite_ref-bb_2-1) [***c***](#cite_ref-bb_2-2) [***d***](#cite_ref-bb_2-3) 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*](https://books.rsc.org/books/monograph/180/Nomenclature-of-Organic-Chemistry). [IUPAC](/source/International_Union_of_Pure_and_Applied_Chemistry)–[RSC](/source/Royal_Society_of_Chemistry). [ISBN](/source/ISBN_(identifier)) [978-0-85404-182-4](https://en.wikipedia.org/wiki/Special:BookSources/978-0-85404-182-4).

1. ^ [***a***](#cite_ref-arag2021_3-0) [***b***](#cite_ref-arag2021_3-1) [***c***](#cite_ref-arag2021_3-2) [***d***](#cite_ref-arag2021_3-3) R. Gamboli, G. Forte, C. Aragona, A. Bevilacqua, M. Bizzarri, V. Unfer (2021): "The use of D-chiro-inositol in clinical practice". *European Review for Medical and Pharmacological Sciences*, volume 25, issue 1, pages 438-446. [doi](/source/Doi_(identifier)):[10.26355/eurrev_202101_24412](https://doi.org/10.26355%2Feurrev_202101_24412)

1. ^ [***a***](#cite_ref-larn2002_4-0) [***b***](#cite_ref-larn2002_4-1) Larner, Joseph (2002). ["D-*chiro*-inositol—its functional role in insulin action and its deficit in insulin resistance"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2478565). *International Journal of Experimental Diabetes Research*. **3** (1): 47–60. [doi](/source/Doi_(identifier)):[10.1080/15604280212528](https://doi.org/10.1080%2F15604280212528). [ISSN](/source/ISSN_(identifier)) [1560-4284](https://search.worldcat.org/issn/1560-4284). [PMC](/source/PMC_(identifier)) [2478565](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2478565). [PMID](/source/PMID_(identifier)) [11900279](https://pubmed.ncbi.nlm.nih.gov/11900279).

1. ^ [***a***](#cite_ref-vasq2021_5-0) [***b***](#cite_ref-vasq2021_5-1) Monastra G, Vazquez-Levin M, Bezerra Espinola MS, Bilotta G, Laganà AS, Unfer V (June 2021). ["D-chiro-inositol, an aromatase down-modulator, increases androgens and reduces estrogens in male volunteers: a pilot study"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8173878). *[Basic and Clinical Andrology](https://en.wikipedia.org/w/index.php?title=Basic_and_Clinical_Andrology&action=edit&redlink=1)*. **31** (1) 13. [doi](/source/Doi_(identifier)):[10.1186/s12610-021-00131-x](https://doi.org/10.1186%2Fs12610-021-00131-x). [PMC](/source/PMC_(identifier)) [8173878](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8173878). [PMID](/source/PMID_(identifier)) [34078260](https://pubmed.ncbi.nlm.nih.gov/34078260).

1. **[^](#cite_ref-sort2017_6-0)** Sortino, Maria A.; Salomone, Salvatore; Carruba, Michele O.; Drago, Filippo (2017-06-08). ["Polycystic Ovary Syndrome: Insights into the Therapeutic Approach with Inositols"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5463048). *Frontiers in Pharmacology*. **8** 341. [doi](/source/Doi_(identifier)):[10.3389/fphar.2017.00341](https://doi.org/10.3389%2Ffphar.2017.00341). [ISSN](/source/ISSN_(identifier)) [1663-9812](https://search.worldcat.org/issn/1663-9812). [PMC](/source/PMC_(identifier)) [5463048](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5463048). [PMID](/source/PMID_(identifier)) [28642705](https://pubmed.ncbi.nlm.nih.gov/28642705).

1. **[^](#cite_ref-kalr2016_7-0)** Kalra, Bharti; Kalra, Sanjay; Sharma, J. B. (2016). ["The inositols and polycystic ovary syndrome"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5040057). *Indian Journal of Endocrinology and Metabolism*. **20** (5): 720–724. [doi](/source/Doi_(identifier)):[10.4103/2230-8210.189231](https://doi.org/10.4103%2F2230-8210.189231). [ISSN](/source/ISSN_(identifier)) [2230-8210](https://search.worldcat.org/issn/2230-8210). [PMC](/source/PMC_(identifier)) [5040057](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5040057). [PMID](/source/PMID_(identifier)) [27730087](https://pubmed.ncbi.nlm.nih.gov/27730087).

1. **[^](#cite_ref-nest2015_8-0)** Nestler, John E.; Unfer, Vittorio (July 2015). "Reflections on inositol(s) for PCOS therapy: steps toward success". *Gynecological Endocrinology*. **31** (7): 501–505. [doi](/source/Doi_(identifier)):[10.3109/09513590.2015.1054802](https://doi.org/10.3109%2F09513590.2015.1054802). [ISSN](/source/ISSN_(identifier)) [1473-0766](https://search.worldcat.org/issn/1473-0766). [PMID](/source/PMID_(identifier)) [26177098](https://pubmed.ncbi.nlm.nih.gov/26177098). [S2CID](/source/S2CID_(identifier)) [207490049](https://api.semanticscholar.org/CorpusID:207490049).

1. **[^](#cite_ref-bizz2014_9-0)** Bizzarri, M.; Carlomagno, G. (July 2014). "Inositol: history of an effective therapy for Polycystic Ovary Syndrome". *European Review for Medical and Pharmacological Sciences*. **18** (13): 1896–1903. [ISSN](/source/ISSN_(identifier)) [2284-0729](https://search.worldcat.org/issn/2284-0729). [PMID](/source/PMID_(identifier)) [25010620](https://pubmed.ncbi.nlm.nih.gov/25010620).

1. **[^](#cite_ref-heim2014_10-0)** Heimark, Douglas; McAllister, Jan; Larner, Joseph (2014). ["Decreased *myo*-inositol to *chiro*-inositol (M/C) ratios and increased M/C epimerase activity in PCOS theca cells demonstrate increased insulin sensitivity compared to controls"](https://doi.org/10.1507%2Fendocrj.ej13-0423). *Endocrine Journal*. **61** (2): 111–117. [doi](/source/Doi_(identifier)):[10.1507/endocrj.ej13-0423](https://doi.org/10.1507%2Fendocrj.ej13-0423). [ISSN](/source/ISSN_(identifier)) [1348-4540](https://search.worldcat.org/issn/1348-4540). [PMID](/source/PMID_(identifier)) [24189751](https://pubmed.ncbi.nlm.nih.gov/24189751).

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Adapted from the Wikipedia article [1D-chiro-Inositol](https://en.wikipedia.org/wiki/1D-chiro-Inositol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/1D-chiro-Inositol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.