Ononitol
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| 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 | |
3D model (JSmol) |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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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]
Biosynthesis
[edit]The enzyme inositol 4-methyltransferase, which has been characterised from Mesembryanthemum crystallinum and Vigna umbellata, catalyses a methylation reaction in which inositol (myo-inositol) is converted to ononitol. The methyl group comes from the cofactor, S-adenosyl methionine (SAM).[4][5]
References
[edit]- ↑ 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.
- ↑ Vernon DM, Bohnert HJ (1992). "A novel methyl transferase induced by osmotic stress in the facultative halophyte Mesembryanthemum crystallinum". EMBO J. 11 (6): 2077–85. doi:10.1002/j.1460-2075.1992.tb05266.x. PMC 556674. PMID 1600940.
- ↑ Wanek W; Richter A (1995). "Purification and characterization of myo-inositol 6-O-methyltransferase from Vigna umbellata Ohwi et Ohashi". Planta. 197 (3): 427–434. Bibcode:1995Plant.197..427W. doi:10.1007/bf00196663.
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