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| Names | |
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| Preferred IUPAC name
(1R,2S,4S,5R)-Cyclohexane-1,2,3,4,5-pentol | |
| Other names
Viburnitol; d-Quercitol; (+)-Quercitol; Proto-quercitol; Acorn sugar | |
| Identifiers | |
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3D model (JSmol) |
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| ChemSpider |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties[1] | |
| C6H12O5 | |
| Molar mass | 164.157 g·mol−1 |
| Appearance | Crystalline solid |
| Melting point | 234 to 235 °C (453 to 455 °F; 507 to 508 K) |
| Soluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
5-Deoxyinositol (quercitol) is a cyclitol. It can be found in wines aged in oak wood barrels.[2] It can also be found in Quercus sp. (oaks)[3] and in Gymnema sylvestre. It is different from quercetol, a synonym of quercetin.
The proposed biosynthesis of 5-deoxyinositol begins with the conversion of D-glucosetomyo-inositol.[4] In this pathway, D-glucose is phosphorylated to form D-glucose-6-phosphate. The NAD+ dependent enzyme inositol 1-phosphate synthase (I1PS) then catalyzes the subsequent oxidation, enolization, aldol cyclization, and reduction of D-glucose 6-phosphate to form myo-inositol 1-phosphate. Hydrolysis of the phosphate group on this molecule gives myo-inositol. Myo-inositol can then be converted into 5-deoxyinositol in three steps,[5] beginning with the oxidation of myo-inositol by inositol dehydrogenase (ID) to form scyllo-inosose. This intermediate is then dehydrated to form a diketone. The reduction of this diketone gives 5-deoxyinositol. This final reduction is thought to be catalyzed by one or more unidentified reductases or dehydrogenases.
