Prenol
3451537
168055575
2007-10-30T11:18:11Z
Edgar181
491706
typo
{{Chembox new
| Reference=<ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/162353 Prenol] at Sigma-Aldrich</ref>
| Name = Prenol
| ImageFile1 = prenol structure.png
| ImageSize1 = 200px
| ImageName1 = Prenol
| ImageFile2 = prenol3D.png
| ImageSize2 = 200px
| ImageName2 = Prenol
| IUPACName = 3-Methyl-2-buten-1-ol
| OtherNames= 3,3-Dimethylallyl alcohol
| Section1 = {{Chembox Identifiers
| CASNo = 556-82-1
| PubChem = 10353732
| SMILES = CC(C)=CCO
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>5</sub>H<sub>10</sub>O
| MolarMass = 86.13 g/mol
| Density = 0.848 g/cm³
| MeltingPt = <25 °C
| BoilingPt = 140 °C
}}
}}
'''Prenol''', or '''3-methyl-2-buten-1-ol''', is a natural [[alcohol]]. It is one of the most simple [[terpene]]s. 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-[CH<sub>2</sub>CCH<sub>3</sub>=CHCH<sub>2</sub>]<sub>n</sub>-OH
The repeating C<sub>5</sub>H<sub>8</sub> [[moiety]] in the brackets is called [[isoprene]].
Prenol is polymerized by [[dehydration reaction]]s; 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]], [[carotenoid]]s, and fat-soluble [[Vitamin A|vitamins A]], [[vitamin E|E]] and [[vitamin K|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==
<references/>
[[Category:flavors]]
[[Category:Terpenes and terpenoids]]
[[Category:Alcohols]]
[[Category:Alkenes]]
[[fr:Prénol]]