2-Heptanone

2-Heptanone[1]
IUPAC name

Heptan-2-one
Other names

Amyl methyl ketone
Butyl acetone
Methyl n-amyl ketone
Methyl pentyl ketone
Identifiers
CAS number 110-43-0 Y
PubChem 8051
ChemSpider 7760 Y
UNII 89VVP1B008 Y
KEGG C08380 Y
ChEBI CHEBI:5672 Y
ChEMBL CHEMBL18893 Y
Jmol-3D images Image 1
Properties
Molecular formula C7H14O
Molar mass 114.18 g/mol
Appearance Clear liquid
Density 0.8 g/mL
Melting point

-35.5 °C
Boiling point

151 °C
Solubility in water 0.4% by wt
Hazards
Flash point 39 °C
Autoignition
temperature		 393 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2-Heptanone, or methyl n-amyl ketone, is a ketone with the molecular formula C7H14O. It is a colorless, water-white liquid with a banana-like, fruity odor.

2-Heptanone is listed by the FDA as a "food additive permitted for direct addition to food for human consumption" (21 CFR 172.515), and it occurs naturally in certain foods (e.g., beer, white bread, butter, various cheeses and potato chips).[2]

The mechanism of action of 2-heptanone as a pheromone at odorant receptors in mice has been investigated.[3]

2-Heptanone is discussed as an alarm pheromone in the urine of rats.[4][5]

2-Heptanone was one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories.[6]

References

  1. ^ Methyl n-amyl ketone, International Occupational Safety and Health Information Centre (CIS)
  2. ^ Methyl (n-amyl) ketone, Chemical Sampling Information, Occupational Safety & Health Administration
  3. ^ Wang, Z., Balet Sindreu, C., Li, V., Nudelman, A., Chan, G.C. and Storm, D.R. (2006). "Pheromonal detection in male mice depends on signaling through the type 3 adenylyl cyclase in the main olfactory epithelium". J. Neurosci. 26 (28): 7375–7379. doi:10.1523/JNEUROSCI.1967-06.2006. PMID 16837584. 
  4. ^ Hauser R, Marczak M, Karaszewski B, Wiergowski M, Kaliszan M, Penkowski M, Kernbach-Wighton G, Jankowski Z, Namieśnik J. (2008). "A preliminary study for identifying olfactory markers of fear in the rat". Lab Anim. (NY) 37 (2): 76–80. doi:10.1038/laban0208-76. PMID 18216798. 
  5. ^ Gutiérrez-García AG, Contreras CM, Mendoza-López MR, García-Barradas O, Cruz-Sánchez JS. (2007). "Urine from stressed rats increases immobility in receptor rats forced to swim: role of 2-heptanone". Physiol. Behav. 91 (1): 166–172. doi:10.1016/j.physbeh.2007.02.006. PMID 17408705. 
  6. ^ Perbellini, L., Brugnone, F., Cocheo, V., De Rosa, E. and Bartolucci, G.B. (1986). "Identification of the n-heptane metabolites in rat and human urine". Arch. Toxicol. 58 (4): 229–234. doi:10.1007/BF00297111. PMID 3718225. 

External links