2-Decanone

2-Decanone
Names
	Other names Decan-2-one; Methyl octyl ketone
Identifiers
CAS Number	693-54-9 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1747463
ChEBI	CHEBI:77929;
ChEMBL	ChEMBL47127;
ChemSpider	12218;
ECHA InfoCard	100.010.685
EC Number	211-752-6;
PubChem CID	12741;
UNII	GX543OLT0R ;
CompTox Dashboard (EPA)	DTXSID9022104 ;
	InChI InChI=1S/C10H20O/c1-3-4-5-6-7-8-9-10(2)11/h3-9H2,1-2H3 Key: ZAJNGDIORYACQU-UHFFFAOYSA-N;
	SMILES CCCCCCCCC(=O)C;
Properties
Chemical formula	C10H20O
Molar mass	156.269 g·mol−1
Appearance	Liquid; Fatty peachy, aldehyde-like aroma
Density	0.821-0.831 (20°)
Melting point	14 °C (57 °F; 287 K)
Boiling point	210 °C (410 °F; 483 K)
Solubility in water	Insoluble. 0.077 mg/mL at 25 °C
Solubility in Fats and oils	Soluble
log P	3.73
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H227, H411
Precautionary statements	P210, P273, P280, P370+P378, P391, P403+P235, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Decanone is a ketone with the chemical formula C₁₀ H₂₀ O.

Occurrence

2-Decanone can be found in meats, dairy products and eggs, fruits (banana, mountain papaya, berries), vegetables (potato, mushroom, endive, soya bean, chayote, kumazase), and grains such as maize, rice, and oats. It also is present in fish, some nuts, honey, ginger, garlic, vanilla, hop oil, mate, brandy, tea, and coffee. It is found in the highest concentrations in milk and hop oil.^[4] 2-Decanone was also found at varying percentages in the essential oils of plants within the Ruta genus, including R. montana and R. chalepensis.^[5]^[6] Within the stem bark of Commiphora rostrata, 2-decanone was found at 69%.^[7]

Applications

2-Decanone has been found to possess strong fumigant activity against the maize weevil.^[8] However, it is less repellent towards the maize weevil than other alkanones.^[7]

Synthesis

2-Decanone can be synthesized by reacting 2-decanol with permanganic acid and copper sulfate in DCM.^[9]

References

^ ^a ^b ^c ^d "Food safety and quality: details". fao.org. Archived from the original on 2023-08-19. Retrieved 2023-08-19.
^ ^a ^b "Human Metabolome Database: Showing metabocard for 2-Decanone (HMDB0031409)". Human Metabolome Database. 2012-09-11. Archived from the original on 2023-06-22. Retrieved 2023-08-19.
^ Wishart, D. S.; Tzur, D.; Knox, C.; Eisner, R.; Guo, A. C.; Young, N.; Cheng, D.; Jewell, K.; Arndt, D.; Sawhney, S.; Fung, C.; Nikolai, L.; Lewis, M.; Coutouly, M.-A.; Forsythe, I.; Tang, P.; Shrivastava, S.; Jeroncic, K.; Stothard, P.; Amegbey, G.; Block, D.; Hau, David. D.; Wagner, J.; Miniaci, J.; Clements, M.; Gebremedhin, M.; Guo, N.; Zhang, Y.; Duggan, G. E.; MacInnis, G. D.; Weljie, A. M.; Dowlatabadi, R.; Bamforth, F.; Clive, D.; Greiner, R.; Li, L.; Marrie, T.; Sykes, B. D.; Vogel, H. J.; Querengesser, L. (2007-01-03). "HMDB: the Human Metabolome Database". Nucleic Acids Research. 35 (Database). Oxford University Press (OUP): D521–D526. doi:10.1093/nar/gkl923. ISSN 0305-1048. PMC 1899095. PMID 17202168.
^ Meeting, Joint FAO/WHO Expert Committee on Food Additives.; Organization, World Health (2011). Evaluation of Certain Food Additives and Contaminants. ISBN 978-92-4-120960-1.
^ Yosra, Bejaoui; Manef, Abderrabba; Sameh, Ayadi (2019). "Biological Study from Ruta Plants Extracts Growing in Tunisia". Iranian Journal of Chemistry and Chemical Engineering. 38 (2). Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR. doi:10.30492/ijcce.2019.37124.
^ Ortu, E.; Sanna, G.; Scala, A.; Pulina, G.; Caboni, P.; Battacone, G. (2016-06-22). "In vitroanthelmintic activity of active compounds of the fringed rueRuta chalepensisagainst dairy ewe gastrointestinal nematodes". Journal of Helminthology. 91 (4). Cambridge University Press (CUP): 447–453. doi:10.1017/s0022149x16000419. ISSN 0022-149X. PMID 27329583.
^ ^a ^b Lwande, W.; Hassanali, A.; Mcdowell, P. G.; Moreka, L.; Nokoe, S. K.; Waterman, P. G. (1992). "Constituents of Commiphora rostrata and some of their analogues as maize weevil, Sitophilus zeamais repellents". International Journal of Tropical Insect Science. 13 (5). Springer Science and Business Media LLC: 679–683. doi:10.1017/s174275840000789x. ISSN 1742-7584. S2CID 85178812.
^ Zunino, María P.; Herrera, Jimena M.; Pizzolitto, Romina P.; Rubinstein, Héctor R.; Zygadlo, Julio A.; Dambolena, José S. (2015-08-18). "Effect of Selected Volatiles on Two Stored Pests: The Fungus Fusarium verticillioides and the Maize Weevil Sithophilus zeamais". Journal of Agricultural and Food Chemistry. 63 (35). American Chemical Society (ACS): 7743–7749. doi:10.1021/acs.jafc.5b02315. hdl:11336/113163. ISSN 0021-8561. PMID 26257042.
^ Lee, Donald G.; Ribagorda, María; Adrio, Javier (2007-03-15). "Potassium Permanganate". Encyclopedia of Reagents for Organic Synthesis. Chichester, UK: John Wiley & Sons, Ltd. doi:10.1002/9780470842898.rp244.pub2. ISBN 978-0-471-93623-7.

[fao.org_h620-1] "Food safety and quality: details". fao.org. Archived from the original on 2023-08-19. Retrieved 2023-08-19.

[Human_Metabolome_Database_2012_u404-2] "Human Metabolome Database: Showing metabocard for 2-Decanone (HMDB0031409)". Human Metabolome Database. 2012-09-11. Archived from the original on 2023-06-22. Retrieved 2023-08-19.

[Wishart_Tzur_Knox_Eisner_2007_pp._D521–D526-3] Wishart, D. S.; Tzur, D.; Knox, C.; Eisner, R.; Guo, A. C.; Young, N.; Cheng, D.; Jewell, K.; Arndt, D.; Sawhney, S.; Fung, C.; Nikolai, L.; Lewis, M.; Coutouly, M.-A.; Forsythe, I.; Tang, P.; Shrivastava, S.; Jeroncic, K.; Stothard, P.; Amegbey, G.; Block, D.; Hau, David. D.; Wagner, J.; Miniaci, J.; Clements, M.; Gebremedhin, M.; Guo, N.; Zhang, Y.; Duggan, G. E.; MacInnis, G. D.; Weljie, A. M.; Dowlatabadi, R.; Bamforth, F.; Clive, D.; Greiner, R.; Li, L.; Marrie, T.; Sykes, B. D.; Vogel, H. J.; Querengesser, L. (2007-01-03). "HMDB: the Human Metabolome Database". Nucleic Acids Research. 35 (Database). Oxford University Press (OUP): D521–D526. doi:10.1093/nar/gkl923. ISSN 0305-1048. PMC 1899095. PMID 17202168.

[Meeting_Organization_2011_p.-4] Meeting, Joint FAO/WHO Expert Committee on Food Additives.; Organization, World Health (2011). Evaluation of Certain Food Additives and Contaminants. ISBN 978-92-4-120960-1.

[Yosra_Manef_Sameh_p.-5] Yosra, Bejaoui; Manef, Abderrabba; Sameh, Ayadi (2019). "Biological Study from Ruta Plants Extracts Growing in Tunisia". Iranian Journal of Chemistry and Chemical Engineering. 38 (2). Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR. doi:10.30492/ijcce.2019.37124.

[Ortu_Sanna_Scala_Pulina_2016_pp._447–453-6] Ortu, E.; Sanna, G.; Scala, A.; Pulina, G.; Caboni, P.; Battacone, G. (2016-06-22). "In vitroanthelmintic activity of active compounds of the fringed rueRuta chalepensisagainst dairy ewe gastrointestinal nematodes". Journal of Helminthology. 91 (4). Cambridge University Press (CUP): 447–453. doi:10.1017/s0022149x16000419. ISSN 0022-149X. PMID 27329583.

[Lwande_Hassanali_Mcdowell_Moreka_1992_pp._679–683-7] Lwande, W.; Hassanali, A.; Mcdowell, P. G.; Moreka, L.; Nokoe, S. K.; Waterman, P. G. (1992). "Constituents of Commiphora rostrata and some of their analogues as maize weevil, Sitophilus zeamais repellents". International Journal of Tropical Insect Science. 13 (5). Springer Science and Business Media LLC: 679–683. doi:10.1017/s174275840000789x. ISSN 1742-7584. S2CID 85178812.

[Zunino_Herrera_Pizzolitto_Rubinstein_2015_pp._7743–7749-8] Zunino, María P.; Herrera, Jimena M.; Pizzolitto, Romina P.; Rubinstein, Héctor R.; Zygadlo, Julio A.; Dambolena, José S. (2015-08-18). "Effect of Selected Volatiles on Two Stored Pests: The Fungus Fusarium verticillioides and the Maize Weevil Sithophilus zeamais". Journal of Agricultural and Food Chemistry. 63 (35). American Chemical Society (ACS): 7743–7749. doi:10.1021/acs.jafc.5b02315. hdl:11336/113163. ISSN 0021-8561. PMID 26257042.

[Lee_Ribagorda_Adrio_2007_p.-9] Lee, Donald G.; Ribagorda, María; Adrio, Javier (2007-03-15). "Potassium Permanganate". Encyclopedia of Reagents for Organic Synthesis. Chichester, UK: John Wiley & Sons, Ltd. doi:10.1002/9780470842898.rp244.pub2. ISBN 978-0-471-93623-7.

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