Geranylacetone
Names | |
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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
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.021.155 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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).
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Geranylacetone is an
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]
References
- ISBN 978-3527306732.
- ISBN 0471238961.
- PMID 15769159.
- .
- PMID 15584954.