Geranylacetone

Geranylacetone
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
CAS Number	3796-70-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:67206;
ChemSpider	1266569;
ECHA InfoCard	100.021.155
EC Number	223-269-8;
PubChem CID	1549778;
UNII	9B7RY79U9Z;
CompTox Dashboard (EPA)	DTXSID4052053 ;
	InChI InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9+ Key: HNZUNIKWNYHEJJ-FMIVXFBMSA-N;
	SMILES CC(=CCC/C(=C/CCC(=O)C)/C)C;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H411
Precautionary statements	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). Infobox references

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]

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

^ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.
^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
^ Pino, Jorge A.; Mesa, Judith; Muñoz, Yamilie; Martí, M. Pilar; Marbot, Rolando (2005). "Volatile Components from Mango (Mangifera indica L.) Cultivars". Journal of Agricultural and Food Chemistry. 53 (6): 2213–2223. doi:10.1021/jf0402633. PMID 15769159.
^ Fruekilde, P.; Hjorth, J.; Jensen, N.R.; Kotzias, D.; Larsen, B. (1998). "Ozonolysis at Vegetation Surfaces". Atmospheric Environment. 32 (11): 1893–1902. doi:10.1016/S1352-2310(97)00485-8.
^ Simkin, Andrew J.; Schwartz, Steven H.; Auldridge, Michele; Taylor, Mark G.; Klee, Harry J. (2004). "The Tomato Carotenoid Cleavage Dioxygenase 1 Genes Contribute to the Formation of the Flavor Volatiles β-Ionone, Pseudoionone, and Geranylacetone". The Plant Journal. 40 (6): 882–892. doi:10.1111/j.1365-313X.2004.02263.x. PMID 15584954.

[1] Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.

[2] Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.

[3] Pino, Jorge A.; Mesa, Judith; Muñoz, Yamilie; Martí, M. Pilar; Marbot, Rolando (2005). "Volatile Components from Mango (Mangifera indica L.) Cultivars". Journal of Agricultural and Food Chemistry. 53 (6): 2213–2223. doi:10.1021/jf0402633. PMID 15769159.

[4] Fruekilde, P.; Hjorth, J.; Jensen, N.R.; Kotzias, D.; Larsen, B. (1998). "Ozonolysis at Vegetation Surfaces". Atmospheric Environment. 32 (11): 1893–1902. doi:10.1016/S1352-2310(97)00485-8.

[5] Simkin, Andrew J.; Schwartz, Steven H.; Auldridge, Michele; Taylor, Mark G.; Klee, Harry J. (2004). "The Tomato Carotenoid Cleavage Dioxygenase 1 Genes Contribute to the Formation of the Flavor Volatiles β-Ionone, Pseudoionone, and Geranylacetone". The Plant Journal. 40 (6): 882–892. doi:10.1111/j.1365-313X.2004.02263.x. PMID 15584954.

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