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	{{DISPLAYTITLE:<small>D</small>-''chiro''-Inositol}}		{{DISPLAYTITLE:1<small>D</small>-''chiro''-Inositol}}
	{{chembox		{{chembox
	\| verifiedrevid = ~~430389778~~		\| verifiedrevid = 443555991
	\| Name = <small>D</small>-''chiro''-Inositol		\| Name = 1<small>D</small>-''chiro''-Inositol
	\| Reference =<ref>'']'', 11th Edition, '''4883'''</ref>		\| Reference =<ref>'']'', 11th Edition, '''4883'''</ref>
	\| ImageFile = D-chiro-inositol.png		\| ImageFile = D-chiro-inositol.png
	\| ImageSize = 125px		\| ImageSize = 125px
	\| ImageName = ''D-~~Chiro~~''-Inositol		\| ImageName = <small>D</small>-''chiro''-Inositol
	\| IUPACName = ~~''cis''-~~1~~,2,4~~-''~~trans~~''-~~3,5,6~~<br />~~-Cyclohexanehexol~~		\| IUPACName = 1<small>D</small>-''chiro''-Inositol<ref name=bb/>
			\| SystematicName = (1''R'',2''R'',3''S'',4''S'',5''S'',6''S'')-Cyclohexane-1,2,3,4,5,6-hexol
	\| OtherNames = DCI <br /> 1,2,4/3,5,6-Hexahydroxycyclohexane
			\| OtherNames = DCI <br /> ''cis''-1,2,4-''trans''-3,5,6<wbr />-Cyclohexanehexol <br /> 1<small>D</small>-1,2,4/3,5,6-Cyclohexanehexol<ref name="bb" /> <br /> 1,2,4/3,5,6-Hexahydroxycyclohexane <br /> (+)-inositol<ref name="bb" />
	\| Section1 = {{Chembox Identifiers		\| Section1 = {{Chembox Identifiers
			\| IUPHAR_ligand = 4645
⚫	\| CASNo = 643-12-9
			\| CASNo_Ref = {{cascite\|correct\|??}}
⚫	\| PubChem =
		⚫	\| CASNo = 643-12-9
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 6R79WV4R10
		⚫	\| PubChem =
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 10254647		\| ChemSpiderID = 10254647
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 27372		\| ChEBI = 27372
	\| SMILES = O1(O)(O)(O)(O)1O		\| SMILES = O1(O)(O)(O)(O)1O
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
Line 23:		Line 29:
	\| Section2 = {{Chembox Properties		\| Section2 = {{Chembox Properties
	\| C=6\|H=12\|O=6		\| C=6\|H=12\|O=6
	\| ~~OpticalActivity~~ = 23/D +55°, c = 1.2 in H<sub>2</sub>O		\| SpecRotation = 23/D +55°, c = 1.2 in H<sub>2</sub>O
	\| MeltingPtC = 230		\| MeltingPtC = 230
	}}		}}
	}}		}}

			'''1<small>D</small>-''chiro''-Inositol'''<ref name=bb/> or '''<small>D</small>-''chiro''-inositol'''<ref name=arag2021/> (often abbreviated '''DCI''') is a ] with formula {{chem2\|C6H12O6}}, one of the nine ]s of ] (which may be collectively called "inositol"). The molecule has a ring of six ] atoms, each bound to one ] atom and one ] (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 ], hence its name. Its ] (mirror compound) is ].
	'''<small>D</small>-''chiro''-Inositol''' (commonly abbreviated '''DCI''') is a member of a family of related substances often referred to collectively as "]," although that term encompasses several ]s of questionable biological relevance. It is known to be an important ] in ] ].<ref>{{cite journal \|author=Larner J \|title=D-chiro-inositol--its functional role in insulin action and its deficit in insulin resistance \|journal=Int. J. Exp. Diabetes Res. \|volume=3 \|issue=1 \|pages=47–60 \|year=2002 \|pmid=11900279 \|doi=10.1080/15604280212528 \|pmc=2478565}}</ref>

			Compared to its more common isomer ], DCI seems to have relatively minor roles in ] and medicine, mostly connected to the biochemistry of ] and other ]s.<ref name=larn2002/><ref name=vasq2021/>
	DCI is not abundant in most diets although it can be found in significant quantities in ] ], and some other foods. It is possible that in higher vertebrates DCI is made from myo-inositol via the action of an ].<ref name="pmid12051772">{{cite journal \|author=Sun TH, Heimark DB, Nguygen T, Nadler JL, Larner J \|title=Both myo-inositol to chiro-inositol epimerase activities and chiro-inositol to myo-inositol ratios are decreased in tissues of GK type 2 diabetic rats compared to Wistar controls \|journal=Biochem. Biophys. Res. Commun. \|volume=293 \|issue=3 \|pages=1092–8 \|year=2002 \|pmid=12051772 \|doi=10.1016/S0006-291X(02)00313-3}}</ref> Contrary to common claims of the non-availability of DCI, it is in fact commercially available to the public as a nutritional supplement in the US.

			==Biochemistry and physiology ==
	DCI appears to have substantial beneficial effects for ], an observation rationalized by the apparent role of DCI in the etiology of PCOS.<ref name="pmid10219066">{{cite journal \|author=Nestler JE, Jakubowicz DJ, Reamer P, Gunn RD, Allan G \|title=Ovulatory and metabolic effects of D-chiro-inositol in the polycystic ovary syndrome \|journal=N. Engl. J. Med. \|volume=340 \|issue=17 \|pages=1314–20 \|year=1999 \|pmid=10219066 \|doi=10.1056/NEJM199904293401703}}</ref><ref name="pmid15251831">{{cite journal \|author=Iuorno MJ, Jakubowicz DJ, Baillargeon JP, ''et al.'' \|title=Effects of d-chiro-inositol in lean women with the polycystic ovary syndrome \|journal=Endocrine practice \|volume=8 \|issue=6 \|pages=417–23 \|year=2002 \|pmid=15251831 \|doi=}}</ref><ref name="pmid11117673">{{cite journal \|author=Nestler JE, Jakubowicz DJ, Iuorno MJ \|title=Role of inositolphosphoglycan mediators of insulin action in the polycystic ovary syndrome \|series=13 \|journal=J. Pediatr. Endocrinol. Metab. \|volume=Suppl 5 \|issue= \|pages=1295–8 \|year=2000 \|pmid=11117673 \|doi=}}</ref> In double-blind studies, women with PCOS who received DCI experienced the following statistically significant benefits when compared with a control group: lowered free and total testosterone, lowered blood pressure, increased insulin sensitivity and a corresponding improvement in glucose disposal, and increased frequency of ovulation. <ref name="pmid10219066"/><ref name="pmid15251831"/>

	==~~Dietary~~ ~~sources~~==		=== Occurrence ===

			The common isomer ''myo''-inositol is converted into DCI in the human body by an ] dependent ], ].<ref name=sort2017/><ref name=kalr2016/><ref name=nest2015/><ref name=bizz2014/><ref name=heim2014/>
	Significant dietary sources include; ] (particularly buckwheat farinetta), ], and '']'' (fig leaf melon).

			===Insulin interactions===
	==See also==
⚫	*]

			D-''chiro''-inositol is known to be an important ] in ] ]. 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.<ref name=larn2002/> In clinical practice, it improves insulin signaling, thus restoring physiological insulin levels in resistant subjects.<ref name=arag2021/>
⚫	==References==
	{{reflist}}

			===Hormonal treatment===
⚫	{{DEFAULTSORT:Inositol, D-chiro-}}
	]

			D-''chiro''-inositol has been used to induce ovulation in women with polycystic ovary syndrome.<ref name=arag2021/>
	]

			DCI depresses the expression of the ] ], which is responsible for the conversion of ] to ].<ref name=arag2021/> One pilot study found males taking DCI had increased androgens and reduced estrogen.<ref name=vasq2021/>

		⚫	== References ==
			<references>

			<ref name=bb>{{BlueBook2013\|rec=104.2.1}}</ref>

			<ref name=vasq2021>{{cite journal \|vauthors=Monastra G, Vazquez-Levin M, Bezerra Espinola MS, Bilotta G, Laganà AS, Unfer V \|title=D-chiro-inositol, an aromatase down-modulator, increases androgens and reduces estrogens in male volunteers: a pilot study \|journal=] \|volume=31 \|issue=1 \|pages=13 \|date=June 2021 \|pmid=34078260 \|pmc=8173878 \|doi=10.1186/s12610-021-00131-x \|url= \|issn= \|doi-access=free }}</ref>

			<ref name=arag2021>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\|10.26355/eurrev_202101_24412}}</ref>

			<ref name=larn2002>{{Cite journal\|last=Larner\|first=Joseph\|date=2002\|title=D-''chiro''-inositol—its functional role in insulin action and its deficit in insulin resistance\|journal=International Journal of Experimental Diabetes Research\|volume=3\|issue=1\|pages=47–60\|doi=10.1080/15604280212528\|issn=1560-4284\|pmc=2478565\|pmid=11900279}}</ref>

			<ref name=heim2014>{{Cite journal\|last1=Heimark\|first1=Douglas\|last2=McAllister\|first2=Jan\|last3=Larner\|first3=Joseph\|date=2014\|title=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\|journal=Endocrine Journal\|volume=61\|issue=2\|pages=111–117\|doi=10.1507/endocrj.ej13-0423\|issn=1348-4540\|pmid=24189751\|doi-access=free}}</ref>

			<ref name=bizz2014>{{Cite journal\|last1=Bizzarri\|first1=M.\|last2=Carlomagno\|first2=G.\|date=July 2014\|title=Inositol: history of an effective therapy for Polycystic Ovary Syndrome\|journal=European Review for Medical and Pharmacological Sciences\|volume=18\|issue=13\|pages=1896–1903\|issn=2284-0729\|pmid=25010620}}</ref>

			<ref name=kalr2016>{{Cite journal\|last1=Kalra\|first1=Bharti\|last2=Kalra\|first2=Sanjay\|last3=Sharma\|first3=J. B.\|date=2016\|title=The inositols and polycystic ovary syndrome\|journal=Indian Journal of Endocrinology and Metabolism\|volume=20\|issue=5\|pages=720–724\|doi=10.4103/2230-8210.189231\|issn=2230-8210\|pmc=5040057\|pmid=27730087 \|doi-access=free }}</ref>

			<ref name=nest2015>{{Cite journal\|last1=Nestler\|first1=John E.\|last2=Unfer\|first2=Vittorio\|date=July 2015\|title=Reflections on inositol(s) for PCOS therapy: steps toward success\|journal= Gynecological Endocrinology\|volume=31\|issue=7\|pages=501–505\|doi=10.3109/09513590.2015.1054802\|issn=1473-0766\|pmid=26177098\|s2cid=207490049}}</ref>

			<ref name=sort2017>{{Cite journal\|last1=Sortino\|first1=Maria A.\|last2=Salomone\|first2=Salvatore\|last3=Carruba\|first3=Michele O.\|last4=Drago\|first4=Filippo\|date=2017-06-08\|title=Polycystic Ovary Syndrome: Insights into the Therapeutic Approach with Inositols\|journal=Frontiers in Pharmacology\|volume=8\|page=341\|doi=10.3389/fphar.2017.00341\|issn=1663-9812\|pmc=5463048\|pmid=28642705\|doi-access=free}}</ref>

			</references>

		⚫	{{DEFAULTSORT:Inositol, D-chiro-}}
		⚫	]

Latest revision as of 12:47, 31 December 2024

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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27372
ChemSpider	10254647
ECHA InfoCard	100.010.359
IUPHAR/BPS	4645
UNII	6R79WV4R10
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/s1Key: CDAISMWEOUEBRE-LKPKBOIGSA-N
SMILES O1(O)(O)(O)(O)1O
Properties
Chemical formula	C₆H₁₂O₆
Molar mass	180.156 g·mol
Melting point	230 °C (446 °F; 503 K)
Chiral rotation (_D)	23/D +55°, c = 1.2 in H₂O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

1D-chiro-Inositol or D-chiro-inositol (often abbreviated DCI) is a chemical substance with formula C₆H₁₂O₆, one of the nine isomers of cyclohexane-1,2,3,4,5,6-hexol (which may be collectively called "inositol"). The molecule has a ring of six carbon atoms, each bound to one hydrogen atom and one 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, hence its name. Its enantiomer (mirror compound) is 1L-chiro-inositol.

Compared to its more common isomer myo-inositol, DCI seems to have relatively minor roles in biochemistry and medicine, mostly connected to the biochemistry of insulin and other hormones.

Biochemistry and physiology

Occurrence

The common isomer myo-inositol is converted into DCI in the human body by an insulin dependent enzyme, NAD/NADH epimerase.

Insulin interactions

D-chiro-inositol is known to be an important secondary messenger in insulin 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. In clinical practice, it improves insulin signaling, thus restoring physiological insulin levels in resistant subjects.

Hormonal treatment

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

DCI depresses the expression of the steroidogenic enzyme aromatase, which is responsible for the conversion of androgens to estrogens. One pilot study found males taking DCI had increased androgens and reduced estrogen.

References

Merck Index, 11th Edition, 4883
^ 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.
^ 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:10.26355/eurrev_202101_24412
^ Larner, Joseph (2002). "D-chiro-inositol—its functional role in insulin action and its deficit in insulin resistance". International Journal of Experimental Diabetes Research. 3 (1): 47–60. doi:10.1080/15604280212528. ISSN 1560-4284. PMC 2478565. PMID 11900279.
^ 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". Basic and Clinical Andrology. 31 (1): 13. doi:10.1186/s12610-021-00131-x. PMC 8173878. PMID 34078260.
Sortino, Maria A.; Salomone, Salvatore; Carruba, Michele O.; Drago, Filippo (2017-06-08). "Polycystic Ovary Syndrome: Insights into the Therapeutic Approach with Inositols". Frontiers in Pharmacology. 8: 341. doi:10.3389/fphar.2017.00341. ISSN 1663-9812. PMC 5463048. PMID 28642705.
Kalra, Bharti; Kalra, Sanjay; Sharma, J. B. (2016). "The inositols and polycystic ovary syndrome". Indian Journal of Endocrinology and Metabolism. 20 (5): 720–724. doi:10.4103/2230-8210.189231. ISSN 2230-8210. PMC 5040057. PMID 27730087.
Nestler, John E.; Unfer, Vittorio (July 2015). "Reflections on inositol(s) for PCOS therapy: steps toward success". Gynecological Endocrinology. 31 (7): 501–505. doi:10.3109/09513590.2015.1054802. ISSN 1473-0766. PMID 26177098. S2CID 207490049.
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 2284-0729. PMID 25010620.
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". Endocrine Journal. 61 (2): 111–117. doi:10.1507/endocrj.ej13-0423. ISSN 1348-4540. PMID 24189751.

Category:

Inositol