2-Heptanone

vanc changed changed 477213486 Methyl n-amyl ketone, International Occupational Safety and Health Information Centre (CIS) correct ?? Skeletal formula of 2-heptanone.svg 200px Skeletal formula of 2-heptanone 2-Heptanone-3D-balls.png Ball-and-stick model of 2-heptanone Heptan-2-one Amyl methyl ketoneButyl acetoneMethyl n-amyl ketoneMethyl pentyl ketone correct FDA 89VVP1B008 correct kegg C08380 1/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3 CATSNJVOTSVZJV-UHFFFAOYAO correct EBI 18893 correct chemspider 1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3 correct chemspider CATSNJVOTSVZJV-UHFFFAOYSA-N correct CAS 110-43-0 8051 correct EBI 5672 O=C(C)CCCCC correct chemspider 7760 C7H14O 114.18 g/mol Clear liquid banana-like, fruity 0.8 g/mL -35.5 151 0.4% by wt 3 mmHg (20 °C) −80.50·10−6 cm3/mol 39 393 TWA 100 ppm (465 mg/m3)0399 1.1% at 151 F C - 7.9% at 250 F C 800 ppm 1670 mg/kg (rat, oral)750 mg/kg (mouse, oral)110430 Methyl (n-amyl) ketone TWA 100 ppm (465 mg/m3) 4000 ppm (rat, 4 hr)2000 ppm (guinea pig, 14.8 hr) 2-Heptanone, also known as methyl n-amyl ketone, or heptan-2-one, is an organic compound with the molecular formula CH3C(O)(CH2)4CH3. It is classified as a ketone. The compound is a colorless, water-like liquid with a banana-like, fruity odor. https://pubchem.ncbi.nlm.nih.gov/compound/8051 2-Heptanone PubChem National Center for Biotechnology Information, U.S. National Library of Medicine 2019-03-07 It contributes to the flavor or odor of several aspects of everyday life. Occurrence and uses thumb|200px|left|The typical odor of gorgonzola is related to 2-heptanone. 2-Heptanone is listed by the U.S. 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).Methyl (n-amyl) ketone, Chemical Sampling Information, Occupational Safety & Health Administration Odor component The mechanism of action of 2-heptanone as a pheromone at odorant receptors in rodents has been investigated. Wang Z, Balet Sindreu C, Li V, Nudelman A, Chan GC, Storm DR 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 July 2006 16837584 6674185 10.1523/JNEUROSCI.1967-06.2006 free Hauser R, Marczak M, Karaszewski B, Wiergowski M, Kaliszan M, Penkowski M, Kernbach-Wighton G, Jankowski Z, Namieśnik J A preliminary study for identifying olfactory markers of fear in the rat Lab Animal 37 2 76–80 February 2008 18216798 10.1038/laban0208-76 7058758 Gutiérrez-García AG, Contreras CM, Mendoza-López MR, García-Barradas O, Cruz-Sánchez JS Urine from stressed rats increases immobility in receptor rats forced to swim: role of 2-heptanone Physiology & Behavior 91 1 166–72 May 2007 17408705 10.1016/j.physbeh.2007.02.006 39613472 2-Heptanone is present in the urine of stressed rats and believe that it is used as a means to alert other rats. Gutiérrez-García AG, Contreras CM, Saldivar-Lara M An alarm pheromone reduces ventral tegmental area-nucleus accumbens shell responsivity Neuroscience Letters 678 16–21 June 2018 29727729 10.1016/j.neulet.2018.04.054 19083563 Certain species of worms are attracted to 2-heptanone and bacteria can use this as a means of pathogenesis. Zhang C, Zhao N, Chen Y, Zhang D, Yan J, Zou W, Zhang K, Huang X 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 November 2016 27660389 5095415 10.1074/jbc.M116.741132 free 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. https://www.bbc.co.uk/news/technology-20080389 BBC News Honey-bees found to have bite that stuns 26 October 2012 Jan 8, 2013 It is one of several compounds that contributes to the odor of sweaty clothing.Source, impact and removal of malodour from soiled clothing 2016 26898151 Denawaka C. J. Fowlis I. A. Dean J. R. Journal of Chromatography A 1438 216–225 10.1016/j.chroma.2016.02.037 free Metabolite 2-Heptanone was one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories. Perbellini L, Brugnone F, Cocheo V, De Rosa E, Bartolucci GB Identification of the n-heptane metabolites in rat and human urine Archives of Toxicology 58 4 229–34 April 1986 3718225 10.1007/BF00297111 22485113 This commonly occurs from exposure to plasticisers. Walker V, Mills GA 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 April 2001 11282094 10.1016/S0009-8981(01)00390-4 2-Heptanone can be absorbed through the skin, inhaled and consumed.https://www.nlm.nih.gov/toxnet/index.html 2-HEPTANONE National Library of Medicine HSDB Database 2019-02-21 Exposure to 2-Heptanone can cause irritation of skin/eyes, respiratory system, headaches, vomiting, and nausea. 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.Liberles Stephen D. Mammalian Pheromones Annual Review of Physiology Annual Reviews 76 1 2014-02-10 0066-4278 10.1146/annurev-physiol-021113-170334 4310675 151–175 23988175 Production 2-Hepthanone is produced via condensation of acetone and butyraldehyde, followed by hydrogenation of the resulting heptenone.Ullmann's Encyclopedia of Industrial Chemistry Ketones 2000 10.1002/14356007.a15_077 978-3-527-30673-2 Siegel H, Eggersdorfer M References External links MSDS for 2-heptanone Methyl (n-amyl) ketone, NIOSH Pocket Guide to Chemical Hazards Category:Heptanones