Prenol

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Prenol[1]
IUPAC name 3-Methyl-2-buten-1-ol
Other names 3,3-Dimethylallyl alcohol
Identifiers
3D model (JSmol)
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Properties
C5H10O
Molar mass 86.13 g/mol
Density 0.848 g/cm³
Melting point
Boiling point
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

  1. Prenol at Sigma-Aldrich



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