2-Heptanone

2-Heptanone[1]
Names
IUPAC name
Heptan-2-one
Other names
Amyl methyl ketone
Butyl acetone
Methyl n-amyl ketone
Methyl pentyl ketone
Identifiers
110-43-0 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:5672 YesY
ChEMBL ChEMBL18893 YesY
ChemSpider 7760 YesY
ECHA InfoCard 100.003.426
KEGG C08380 YesY
PubChem 8051
UNII 89VVP1B008 YesY
Properties
C7H14O
Molar mass 114.18 g/mol
Appearance Clear liquid
Odor banana-like, fruity[2]
Density 0.8 g/mL
Melting point −35.5 °C (−31.9 °F; 237.7 K)
Boiling point 151 °C (304 °F; 424 K)
0.4% by wt
Vapor pressure 3 mmHg (20°C)[2]
Hazards
Flash point 39 °C (102 °F; 312 K)
393 °C (739 °F; 666 K)
Explosive limits 1.1% at 151 °F (66 °C) - 7.9% at 250 °F (121 °C)[2]
Lethal dose or concentration (LD, LC):
1670 mg/kg (rat, oral)
750 mg/kg (mouse, oral)[3]
4000 ppm (rat, 4 hr)
2000 ppm (guinea pig, 14.8 hr)[3]
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 100 ppm (465 mg/m3)[2]
REL (Recommended)
 TWA 100 ppm (465 mg/m3)[2]
IDLH (Immediate danger)
 800 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

The typical smell of gorgonzola is related to 2-heptanone.

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).[4]

The mechanism of action of 2-heptanone as a pheromone at odorant receptors in rodents has been investigated.[5][6][7]

2-Heptanone has also been found to be excreted by honey bees when they bite small pests within the colony such as wax moth larvae and Varroa mites. Though it was historically believed to be an alarm pheromone, 2-heptanone has been shown to act as an anaesthetic on the pests, enabling the honey bee to stun the pest and eject it from the hive. The work could lead to the use of 2-Heptanone as an alternative local anaesthetic to lidocaine, which although well established for clinical use, has the disadvantage of provoking allergic reactions in some people.[8]

2-Heptanone was one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories.[9]

References

  1. ↑ Methyl n-amyl ketone, International Occupational Safety and Health Information Centre (CIS)
  2. 1 2 3 4 5 6 "NIOSH Pocket Guide to Chemical Hazards #0399". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 "Methyl (n-amyl) ketone". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ Methyl (n-amyl) ketone, Chemical Sampling Information, Occupational Safety & Health Administration
  5. ↑ Wang, Z.; Balet Sindreu, C.; Li, V.; Nudelman, A.; Chan, G.C. & 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ "Honey-bees found to have bite that stuns". BBC News. 26 October 2012. Retrieved Jan 8, 2013.
  9. ↑ Perbellini, L.; Brugnone, F.; Cocheo, V.; De Rosa, E. & 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

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