Geranylacetone
Chemical compound
From Wikipedia, the free encyclopedia
Geranylacetone is an organic compound with the formula CH3C(O)(CH2)2CH=C(CH3)(CH2)2CH=C(CH3)2. A colorless oil, it is the product of coupling geranyl and acetonyl groups. It is a precursor to synthetic squalene.[1]
 | |
| Names | |
|---|---|
| Preferred IUPAC name
(5E)-6,10-Dimethylundeca-5,9-dien-2-one | |
| Other names
6,10-dimethyl-(5E)-5,9-undecadien-2-one, (E)-geranylacetone | |
| Identifiers | |
3D model (JSmol) |
|
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.021.155 |
| EC Number |
|
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C13H22O | |
| Molar mass | 194.318 g·mol−1 |
| Density | 0.8698 g/cm3 (20 °C) |
| Boiling point | 126–8 °C (259–46 °F; 399–281 K) 10 mm Hg |
| Hazards | |
| GHS labelling: | |
  | |
| Warning | |
| H315, H411 | |
| P264, P273, P280, P302+P352, P321, P332+P313, P362, P391, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Synthesis and occurrence
Geranylacetone can be produced by transesterification of ethyl acetoacetate with linalool:
- EtOC(O)CH2C(O)CH3 + C10H17OH → C10H17OC(O)CH2C(O)CH3 + EtOH
The esterification of linalool can also be effected with ketene or isopropenyl methyl ether. The resulting linalyl ester undergoes Carroll rearrangement to give geranylacetone. Geranyl acetone is a precursor to isophytol, which is used in the manufacture of Vitamin E. Other derivatives of geranyl acetone are farnesol and nerolidol.[2]
Geranylacetone is a flavor component of many plants including rice, mango,[3] and tomatoes.
Together with other ketones, geranylacetone results from the degradation of vegetable matter by ozone.[4]
Biosynthesis
It arises by the oxidation of certain carotenoids. Such reaction are catalyzed by carotenoid oxygenase.[5]