Ononitol

Ononitol
Names
	IUPAC name 4-O-methyl-myo-inositol
	Systematic IUPAC name (1R,2S,3S,4S,5S,6S)-6-Methoxycyclohexane-1,2,3,4,5-pentol
Identifiers
CAS Number	6090-97-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18266 ;
ChemSpider	21864849 ;
DrugBank	DB12969;
KEGG	C06352;
PubChem CID	164619;
UNII	A998ME07KR;
CompTox Dashboard (EPA)	DTXSID601029635 ;
	InChI InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6-,7-/m0/s1 Key: DSCFFEYYQKSRSV-GESKJZQWSA-N ; InChI=1/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6-,7-/m0/s1;
	SMILES CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H]([C@@H]1O)O)O)O)O;
Properties
Chemical formula	C7H14O6
Molar mass	194.183 g·mol−1
Appearance	colorless solid
Melting point	167–169 °C (333–336 °F; 440–442 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ononitol is an organic compound with the formula (CHOH)₅(CHOCH₃). It is derivative of inositol, specifically 4-O-methyl-myo-inositol: an ether that can be described as the result of replacing the hydroxyl (–OH) in position 4 of myo-inositol by a methoxy group.

This compound occurs in several organisms.^[1] It is one of the predominant soluble carbohydrate derivatives in the root nodules of the pea plant created by the bacterium Rhizobium leguminosarum,^[2] and a constituent of Medicago sativa.^[3]

References

^ Singh, Madhulika; Kumar, Jitendra; Singh, Samiksha; Singh, Vijay Pratap; Prasad, Sheo Mohan (2015). "Roles of osmoprotectants in improving salinity and drought tolerance in plants: A review". Reviews in Environmental Science and Bio/Technology. 14 (3): 407–426. Bibcode:2015RESBT..14..407S. doi:10.1007/s11157-015-9372-8.
^ Lief Skøt, Helge Egsgaard (1984): "Identification of ononitol and O-methyl-scyllo-inositol in pea root nodules". Planta, volume 161, pages 32–36. doi:10.1007/BF00951457
^ E. A. McComb and V. V. Rendig (1962). "Ononitol (4-O-methyl-myo-inositol) as a constituent of Medicago sativa". Archives of Biochemistry and Biophysics. 99 (1): 192–193. doi:10.1016/0003-9861(62)90261-8.

[1] Singh, Madhulika; Kumar, Jitendra; Singh, Samiksha; Singh, Vijay Pratap; Prasad, Sheo Mohan (2015). "Roles of osmoprotectants in improving salinity and drought tolerance in plants: A review". Reviews in Environmental Science and Bio/Technology. 14 (3): 407–426. Bibcode:2015RESBT..14..407S. doi:10.1007/s11157-015-9372-8.

[skot1984-2] Lief Skøt, Helge Egsgaard (1984): "Identification of ononitol and O-methyl-scyllo-inositol in pea root nodules". Planta, volume 161, pages 32–36. doi:10.1007/BF00951457

[mcco1962-3] E. A. McComb and V. V. Rendig (1962). "Ononitol (4-O-methyl-myo-inositol) as a constituent of Medicago sativa". Archives of Biochemistry and Biophysics. 99 (1): 192–193. doi:10.1016/0003-9861(62)90261-8.

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