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Prenol
| Prenol[1]
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| IUPAC name
| 3-Methyl-2-buten-1-ol
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| Other names
| 3,3-Dimethylallyl alcohol
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| Identifiers
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| CAS number
| 556-82-1
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| PubChem
| 10353732
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| SMILES
| CC(C)=CCO
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| Properties
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| Molecular formula
| C5H10O
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| Molar mass
| 86.13 g/mol
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| Density
| 0.848 g/cm³
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| Melting point
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<25 °C
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| Boiling point
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140 °C
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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.
References
- ^ Prenol at Sigma-Aldrich
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Prenol". A list of authors is available in Wikipedia.
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