| Prenol[1] | |
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| IUPAC name | 3-Methyl-2-buten-1-ol |
| Other names | 3,3-Dimethylallyl alcohol |
| Identifiers | |
| CAS number | 556-82-1 |
| PubChem | |
| SMILES |
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| Properties | |
| Molecular formula | C5H10O |
| Molar mass | 86.13 g/mol |
| Density | 0.848 g/cm³ |
| Melting point |
<25 °C |
| Boiling point |
140 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Prenol, or 3-methyl-2-buten-1-ol, is a natural alcohol. It is one of the most simple terpenes. It is a clear colorless oil that is insoluble in water, but miscible with most common organic solvents. It has a fruity odor and is used occasionally in perfumery.
It is also a building block of isoprenoid alcohols (or 'prenol'), which have the general formula:
The repeating C5H8 moiety in the brackets is called isoprene.
Prenol is polymerized by dehydration reactions; when there are at least four isoprene units (n in the above formula is greater than or equal to four), the polymer is called a polyprenol. Polyprenols can contain up to 100 isoprene units (n=100) linked end to end with the hydroxyl group (-OH) remaining at the end. These isoprenoid alcohols are also called ‘terpenols’ These isoprenoid alcohols are important in the acylation of proteins, carotenoids, and fat-soluble vitamins A, E and K. They are also building blocks for plant oils such as farnesol and geraniol. Prenol is also a building block of cholesterol (built from six isoprene units), and thus of all steroids. Prenol has sedative properities, it is probably GABA receptor allosteric modulator
When the isoprene unit attached to the alcohol is saturated, the compound is referred to as a dolichol. Dolichols are important as glycosyl carriers in the synthesis of polysaccharides.