2-Decanone

{{Chembox

| Name = 2-Decanone

| ImageFile = File:2-decanone structure.svg

| OtherNames = Decan-2-one
Methyl octyl ketone

| Section1 = {{Chembox Identifiers

| CASNo = 693-54-9

| CASNo_Ref = {{cascite|correct|CAS}}

| Beilstein = 1747463

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = GX543OLT0R

| PubChem = 12741

| ChemSpiderID = 12218

| EC_number = 211-752-6

| ChEBI = 77929

| ChEMBL = 47127

| StdInChI = 1S/C10H20O/c1-3-4-5-6-7-8-9-10(2)11/h3-9H2,1-2H3

| StdInChIKey = ZAJNGDIORYACQU-UHFFFAOYSA-N

| SMILES = CCCCCCCCC(=O)C

}}

| Section2 = {{Chembox Properties

| C=10|H=20|O=1

| Appearance = Liquid; Fatty peachy, aldehyde-like aroma{{cite web | title=Food safety and quality: details | website=fao.org | url=https://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/details/en/c/2050/ | access-date=2023-08-19 | archive-date=2023-08-19 | archive-url=https://web.archive.org/web/20230819044233/https://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/details/en/c/2050/ | url-status=live }}

| Density = 0.821-0.831 (20°)

| Solubility = Insoluble. 0.077 mg/mL at 25 °C{{cite web | title=Human Metabolome Database: Showing metabocard for 2-Decanone (HMDB0031409) | website=Human Metabolome Database | date=2012-09-11 | url=https://hmdb.ca/metabolites/HMDB0031409 | access-date=2023-08-19 | archive-date=2023-06-22 | archive-url=https://web.archive.org/web/20230622120248/https://hmdb.ca/metabolites/HMDB0031409 | url-status=live }}

| SolubleOther = Soluble

| Solvent = Fats and oils

| MeltingPtC = 14

| BoilingPtC = 210

| LogP = 3.73{{cite journal | last1=Wishart | first1=D. S. | last2=Tzur | first2=D. | last3=Knox | first3=C. | last4=Eisner | first4=R. | last5=Guo | first5=A. C. | last6=Young | first6=N. | last7=Cheng | first7=D. | last8=Jewell | first8=K. | last9=Arndt | first9=D. | last10=Sawhney | first10=S. | last11=Fung | first11=C. | last12=Nikolai | first12=L. | last13=Lewis | first13=M. | last14=Coutouly | first14=M.-A. | last15=Forsythe | first15=I. | last16=Tang | first16=P. | last17=Shrivastava | first17=S. | last18=Jeroncic | first18=K. | last19=Stothard | first19=P. | last20=Amegbey | first20=G. | last21=Block | first21=D. | last22=Hau | first22=David. D. | last23=Wagner | first23=J. | last24=Miniaci | first24=J. | last25=Clements | first25=M. | last26=Gebremedhin | first26=M. | last27=Guo | first27=N. | last28=Zhang | first28=Y. | last29=Duggan | first29=G. E. | last30=MacInnis | first30=G. D. | last31=Weljie | first31=A. M. | last32=Dowlatabadi | first32=R. | last33=Bamforth | first33=F. | last34=Clive | first34=D. | last35=Greiner | first35=R. | last36=Li | first36=L. | last37=Marrie | first37=T. | last38=Sykes | first38=B. D. | last39=Vogel | first39=H. J. | last40=Querengesser | first40=L. | title=HMDB: the Human Metabolome Database | journal=Nucleic Acids Research | publisher=Oxford University Press (OUP) | volume=35 | issue=Database | date=2007-01-03 | issn=0305-1048 | doi=10.1093/nar/gkl923 | pages=D521–D526| pmid=17202168 | pmc=1899095 }}

}}

| Section3 =

| Section4 =

| Section5 =

| Section6 = {{Chembox Hazards

| GHSPictograms = {{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|227|411}}

| PPhrases = {{P-phrases|210|273|280|370+378|391|403+235|501}}

}}

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.{{cite book | last1=Meeting | first1=Joint FAO/WHO Expert Committee on Food Additives. | last2=Organization | first2=World Health | title=Evaluation of Certain Food Additives and Contaminants | date=2011 | isbn=978-92-4-120960-1 | page=}} 2-Decanone was also found at varying percentages in the essential oils of plants within the Ruta genus, including R. montana and R. chalepensis.{{cite journal | last1=Yosra | first1=Bejaoui | last2=Manef | first2=Abderrabba | last3=Sameh | first3=Ayadi | title=Biological Study from Ruta Plants Extracts Growing in Tunisia | journal=Iranian Journal of Chemistry and Chemical Engineering | date=2019 | publisher=Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR | volume=38 | issue=2 | doi=10.30492/ijcce.2019.37124 | page=}}{{cite journal | last1=Ortu | first1=E. | last2=Sanna | first2=G. | last3=Scala | first3=A. | last4=Pulina | first4=G. | last5=Caboni | first5=P. | last6=Battacone | first6=G. | title=In vitroanthelmintic activity of active compounds of the fringed rueRuta chalepensisagainst dairy ewe gastrointestinal nematodes | journal=Journal of Helminthology | publisher=Cambridge University Press (CUP) | volume=91 | issue=4 | date=2016-06-22 | issn=0022-149X | doi=10.1017/s0022149x16000419 | pages=447–453| pmid=27329583 }} Within the stem bark of Commiphora rostrata, 2-decanone was found at 69%.{{cite journal | last1=Lwande | first1=W. | last2=Hassanali | first2=A. | last3=Mcdowell | first3=P. G. | last4=Moreka | first4=L. | last5=Nokoe | first5=S. K. | last6=Waterman | first6=P. G. | title=Constituents of Commiphora rostrata and some of their analogues as maize weevil, Sitophilus zeamais repellents | journal=International Journal of Tropical Insect Science | publisher=Springer Science and Business Media LLC | volume=13 | issue=5 | year=1992 | issn=1742-7584 | doi=10.1017/s174275840000789x | pages=679–683| s2cid=85178812 }}

Applications

2-Decanone has been found to possess strong fumigant activity against the maize weevil.{{cite journal | last1=Zunino | first1=María P. | last2=Herrera | first2=Jimena M. | last3=Pizzolitto | first3=Romina P. | last4=Rubinstein | first4=Héctor R. | last5=Zygadlo | first5=Julio A. | last6=Dambolena | first6=José S. | title=Effect of Selected Volatiles on Two Stored Pests: The Fungus Fusarium verticillioides and the Maize Weevil Sithophilus zeamais | journal=Journal of Agricultural and Food Chemistry | publisher=American Chemical Society (ACS) | volume=63 | issue=35 | date=2015-08-18 | issn=0021-8561 | doi=10.1021/acs.jafc.5b02315 | pages=7743–7749| pmid=26257042 | hdl=11336/113163 | hdl-access=free }} However, it is less repellent towards the maize weevil than other alkanones.

Synthesis

2-Decanone can be synthesized by reacting 2-decanol with permanganic acid and copper sulfate in DCM.{{cite book | last1=Lee | first1=Donald G. | last2=Ribagorda | first2=María | last3=Adrio | first3=Javier | title=Encyclopedia of Reagents for Organic Synthesis | chapter=Potassium Permanganate | publisher=John Wiley & Sons, Ltd | publication-place=Chichester, UK | date=2007-03-15 | isbn=978-0-471-93623-7 | doi=10.1002/9780470842898.rp244.pub2 | page=}}

References

Category:Ketones