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2-Heptanone

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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-like liquid with a banana-like, fruity odor. 2-Heptanone has a neutral formal charge, and is only slightly soluble in water.[4] It is one of several compounds that contributes to the odor of sweaty clothing.[5]

2-Heptanone[1]
Skeletal formula of 2-heptanone
Ball-and-stick model of 2-heptanone
Names
Preferred IUPAC name
Heptan-2-one
Other names
Amyl methyl ketone
Butyl acetone
Methyl n-amyl ketone
Methyl pentyl ketone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.426 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3 checkY
    Key: CATSNJVOTSVZJV-UHFFFAOYSA-N checkY
  • InChI=1/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3
    Key: CATSNJVOTSVZJV-UHFFFAOYAO
  • O=C(C)CCCCC
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]
-80.50·10−6 cm3/mol
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]
NIOSH (US health exposure limits):
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).
checkY verify (what is checkY☒N ?)
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).[6]

The mechanism of action of 2-heptanone as a pheromone at odorant receptors in rodents has been investigated.[7][8][9] 2-Heptanone is present in the urine of stressed rats and believe that it is used as a means to alert other rats.[9][10] Certain species of worms are attracted to 2-heptanone and bacteria can use this as a means of pathogenesis.[11] 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.[12]

2-Heptanone was one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories.[13] This commonly occurs from exposure to plasticisers.[14] 2-Heptanone can be absorbed through the skin, inhaled and consumed.[15] Exposure to 2-Heptanone can cause irritation of skin/eyes, respiratory system, headaches, vomiting, and nausea.[15]

In mice 2-H is a urinary component and pheromone. It has a high affinity for the main olfactory epithelium. Gaillard et al 2002 found that it agonizes one specific olfactory receptor, and that that OR only binds 2-H.[16]

References

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  1. ^ Methyl n-amyl ketone, International Occupational Safety and Health Information Centre (CIS)
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0399". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b "Methyl (n-amyl) ketone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "2-Heptanone". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2019-03-07.
  5. ^ Denawaka CJ, Fowlis IA, Dean JR (2016). "Source, impact and removal of malodour from soiled clothing". Journal of Chromatography A. 1438: 216–225. doi:10.1016/j.chroma.2016.02.037. PMID 26898151.
  6. ^ Methyl (n-amyl) ketone, Chemical Sampling Information, Occupational Safety & Health Administration
  7. ^ Wang Z, Balet Sindreu C, Li V, Nudelman A, Chan GC, Storm DR (July 2006). "Pheromone detection in male mice depends on signaling through the type 3 adenylyl cyclase in the main olfactory epithelium". The Journal of Neuroscience. 26 (28): 7375–9. doi:10.1523/JNEUROSCI.1967-06.2006. PMC 6674185. PMID 16837584.
  8. ^ Hauser R, Marczak M, Karaszewski B, Wiergowski M, Kaliszan M, Penkowski M, Kernbach-Wighton G, Jankowski Z, Namieśnik J (February 2008). "A preliminary study for identifying olfactory markers of fear in the rat". Lab Animal. 37 (2): 76–80. doi:10.1038/laban0208-76. PMID 18216798. S2CID 7058758.
  9. ^ a b Gutiérrez-García AG, Contreras CM, Mendoza-López MR, García-Barradas O, Cruz-Sánchez JS (May 2007). "Urine from stressed rats increases immobility in receptor rats forced to swim: role of 2-heptanone". Physiology & Behavior. 91 (1): 166–72. doi:10.1016/j.physbeh.2007.02.006. PMID 17408705. S2CID 39613472.
  10. ^ Gutiérrez-García AG, Contreras CM, Saldivar-Lara M (June 2018). "An alarm pheromone reduces ventral tegmental area-nucleus accumbens shell responsivity". Neuroscience Letters. 678: 16–21. doi:10.1016/j.neulet.2018.04.054. PMID 29727729. S2CID 19083563.
  11. ^ Zhang C, Zhao N, Chen Y, Zhang D, Yan J, Zou W, Zhang K, Huang X (November 2016). "The Signaling Pathway of Caenorhabditis elegans Mediates Chemotaxis Response to the Attractant 2-Heptanone in a Trojan Horse-like Pathogenesis". The Journal of Biological Chemistry. 291 (45): 23618–23627. doi:10.1074/jbc.M116.741132. PMC 5095415. PMID 27660389.
  12. ^ "Honey-bees found to have bite that stuns". BBC News. 26 October 2012. Retrieved Jan 8, 2013.
  13. ^ Perbellini L, Brugnone F, Cocheo V, De Rosa E, Bartolucci GB (April 1986). "Identification of the n-heptane metabolites in rat and human urine". Archives of Toxicology. 58 (4): 229–34. doi:10.1007/BF00297111. PMID 3718225. S2CID 22485113.
  14. ^ Walker V, Mills GA (April 2001). "Urine 4-heptanone: a beta-oxidation product of 2-ethylhexanoic acid from plasticisers". Clinica Chimica Acta; International Journal of Clinical Chemistry. 306 (1–2): 51–61. doi:10.1016/S0009-8981(01)00390-4. PMID 11282094.
  15. ^ a b "2-HEPTANONE". National Library of Medicine HSDB Database. Retrieved 2019-02-21.
  16. ^ Liberles SD (2014-02-10). "Mammalian Pheromones". Annual Review of Physiology. 76 (1). Annual Reviews: 151–175. doi:10.1146/annurev-physiol-021113-170334. ISSN 0066-4278. PMC 4310675. PMID 23988175.
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