Prenol
From Wikipedia, the free encyclopedia
| 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 | CC(C)=CCO |
| 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 disclaimer and 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:
- H-[CH2CCH3=CHCH2]n-OH
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.
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.
