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Revision as of 17:20, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443315087 of page 2-Heptanone for the Chem/Drugbox validation project (updated: '').  Latest revision as of 21:49, 12 June 2024 edit Thegreatluigi (talk | contribs)Extended confirmed users, Rollbackers12,195 editsm Reverted edit by 199.5.150.66 (talk) to last version by Maxim MasiutinTag: Rollback 
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{{cs1 config|name-list-style=vanc}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedimages = changed
⚫ | verifiedrevid = 443314270
| Watchedfields = changed
⚫ | verifiedrevid = 477213486
| Reference = <ref>, International Occupational Safety and Health Information Centre (CIS)</ref> | Reference = <ref>, International Occupational Safety and Health Information Centre (CIS)</ref>
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = 2-heptanone.svg | ImageFile = Skeletal formula of 2-heptanone.svg
| ImageSize = 170px | ImageSize = 200px
| ImageName = Skeletal formula of 2-heptanone | ImageName = Skeletal formula of 2-heptanone
| ImageFile1 = 2-Heptanone-3D-balls.png | ImageFile1 = 2-Heptanone-3D-balls.png
| ImageSize1 = 200px | ImageSize1 =
| ImageName1 = Ball-and-stick model of 2-heptanone | ImageName1 = Ball-and-stick model of 2-heptanone
| IUPACName = Heptan-2-one | PIN = Heptan-2-one
| OtherNames = Amyl methyl ketone<br>Butyl acetone<br>Methyl ''n''-amyl ketone<br>Methyl pentyl ketone | OtherNames = Amyl methyl ketone<br>Butyl acetone<br>Methyl ''n''-amyl ketone<br>Methyl pentyl ketone
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 89VVP1B008 | UNII = 89VVP1B008
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
Line 27: Line 29:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 110-43-0 | CASNo = 110-43-0
| PubChem = 8051 | PubChem = 8051
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 5672 | ChEBI = 5672
| SMILES = O=C(C)CCCCC | SMILES = O=C(C)CCCCC
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7760 | ChemSpiderID = 7760
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>7</sub>H<sub>14</sub>O | Formula = C<sub>7</sub>H<sub>14</sub>O
| MolarMass = 114.18 g/mol | MolarMass = 114.18 g/mol
| Appearance = Clear liquid | Appearance = Clear liquid
| Odor = banana-like, fruity<ref name=NIOSH/>
| Density = 0.8 g/mL
| MeltingPt = -35.5 °C | Density = 0.8 g/mL
| BoilingPt = 151 °C | MeltingPtC = -35.5
| MeltingPt_notes =
⚫ | Solubility = 0.4% by wt
| BoilingPtC = 151
| BoilingPt_notes =
⚫ | Solubility = 0.4% by wt
| VaporPressure = 3 mmHg (20°C)<ref name=NIOSH/>
| MagSus = -80.50·10<sup>−6</sup> cm<sup>3</sup>/mol
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = 39 °C | FlashPtC = 39
| Autoignition = 393 °C | AutoignitionPtC = 393
| PEL = TWA 100 ppm (465 mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0399}}</ref>
| ExploLimits = 1.1% at {{convert|151|F|C}} - 7.9% at {{convert|250|F|C}}<ref name=NIOSH/>
| IDLH = 800 ppm<ref name=NIOSH/>
| LD50 = 1670 mg/kg (rat, oral)<br/>750 mg/kg (mouse, oral)<ref name=IDLH>{{IDLH|110430|Methyl (n-amyl) ketone}}</ref>
| REL = TWA 100 ppm (465 mg/m<sup>3</sup>)<ref name=NIOSH/>
| LCLo = 4000 ppm (rat, 4 hr)<br/>2000 ppm (guinea pig, 14.8 hr)<ref name=IDLH/>
}} }}
}} }}
'''2-Heptanone''', also known as '''methyl ''n''-amyl ketone''', or '''Heptan-2-one''', is a ] with the ] C<sub>7</sub>H<sub>14</sub>O. 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.<ref>{{cite web |url= https://pubchem.ncbi.nlm.nih.gov/compound/8051 |title= 2-Heptanone | work = PubChem | publisher = National Center for Biotechnology Information, U.S. National Library of Medicine |access-date=2019-03-07 }}</ref> It is one of several compounds that contributes to the odor of sweaty clothing.<ref name=sweat>{{cite journal|title=Source, impact and removal of malodour from soiled clothing|date=2016 |pmid=26898151 |last1=Denawaka |first1=C. J. |last2=Fowlis |first2=I. A. |last3=Dean |first3=J. R. |journal=Journal of Chromatography A |volume=1438 |pages=216–225 |doi=10.1016/j.chroma.2016.02.037 |doi-access=free }}</ref>

] 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).<ref>, Chemical Sampling Information, Occupational Safety & Health Administration</ref>

The mechanism of action of 2-heptanone as a pheromone at odorant receptors in rodents has been investigated.<ref>{{cite journal | vauthors = Wang Z, Balet Sindreu C, Li V, Nudelman A, Chan GC, Storm DR | title = Pheromone detection in male mice depends on signaling through the type 3 adenylyl cyclase in the main olfactory epithelium | journal = The Journal of Neuroscience | volume = 26 | issue = 28 | pages = 7375–9 | date = July 2006 | pmid = 16837584 | pmc=6674185|doi = 10.1523/JNEUROSCI.1967-06.2006 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Hauser R, Marczak M, Karaszewski B, Wiergowski M, Kaliszan M, Penkowski M, Kernbach-Wighton G, Jankowski Z, Namieśnik J | title = A preliminary study for identifying olfactory markers of fear in the rat | journal = Lab Animal | volume = 37 | issue = 2 | pages = 76–80 | date = February 2008 | pmid = 18216798 | doi = 10.1038/laban0208-76 | s2cid = 7058758 }}</ref><ref name="Urine from stressed rats increases">{{cite journal | vauthors = Gutiérrez-García AG, Contreras CM, Mendoza-López MR, García-Barradas O, Cruz-Sánchez JS | title = Urine from stressed rats increases immobility in receptor rats forced to swim: role of 2-heptanone | journal = Physiology & Behavior | volume = 91 | issue = 1 | pages = 166–72 | date = May 2007 | pmid = 17408705 | doi = 10.1016/j.physbeh.2007.02.006 | s2cid = 39613472 }}</ref> 2-Heptanone is present in the urine of stressed rats and believe that it is used as a means to alert other rats.<ref name="Urine from stressed rats increases"/><ref>{{cite journal | vauthors = Gutiérrez-García AG, Contreras CM, Saldivar-Lara M | title = An alarm pheromone reduces ventral tegmental area-nucleus accumbens shell responsivity | journal = Neuroscience Letters | volume = 678 | pages = 16–21 | date = June 2018 | pmid = 29727729 | doi = 10.1016/j.neulet.2018.04.054 | s2cid = 19083563 }}</ref> Certain species of worms are attracted to 2-heptanone and bacteria can use this as a means of ].<ref>{{cite journal | vauthors = Zhang C, Zhao N, Chen Y, Zhang D, Yan J, Zou W, Zhang K, Huang X | title = The Signaling Pathway of Caenorhabditis elegans Mediates Chemotaxis Response to the Attractant 2-Heptanone in a Trojan Horse-like Pathogenesis | journal = The Journal of Biological Chemistry | volume = 291 | issue = 45 | pages = 23618–23627 | date = November 2016 | pmid = 27660389 | pmc = 5095415 | doi = 10.1074/jbc.M116.741132 | doi-access = free }}</ref> 2-Heptanone has also been found to be excreted by honey bees when they bite small pests within the colony such as ] larvae and ]. 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.<ref>{{Cite news | url = https://www.bbc.co.uk/news/technology-20080389 | publisher = BBC News | title = Honey-bees found to have bite that stuns | date = 26 October 2012 | access-date = Jan 8, 2013}}</ref>

2-Heptanone was one of the metabolites of ''n''-] found in the urine of employees exposed to heptane in shoe and tire factories.<ref>{{cite journal | vauthors = Perbellini L, Brugnone F, Cocheo V, De Rosa E, Bartolucci GB | title = Identification of the n-heptane metabolites in rat and human urine | journal = Archives of Toxicology | volume = 58 | issue = 4 | pages = 229–34 | date = April 1986 | pmid = 3718225 | doi = 10.1007/BF00297111 | s2cid = 22485113 }}</ref> This commonly occurs from exposure to ].<ref name=":0">{{cite journal | vauthors = Walker V, Mills GA | title = Urine 4-heptanone: a beta-oxidation product of 2-ethylhexanoic acid from plasticisers | journal = Clinica Chimica Acta; International Journal of Clinical Chemistry | volume = 306 | issue = 1–2 | pages = 51–61 | date = April 2001 | pmid = 11282094 | doi = 10.1016/S0009-8981(01)00390-4 }}</ref> 2-Heptanone can be absorbed through the skin, inhaled and consumed.<ref name=":1">{{cite web|url=https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+1122|title=2-HEPTANONE | work = National Library of Medicine HSDB Database |access-date=2019-02-21 }}</ref> Exposure to 2-Heptanone can cause irritation of skin/eyes, respiratory system, headaches, vomiting, and nausea.<ref name=":1" />

In ] 2-H is a ] component and ]. It has a high ] for the main ]. Gaillard et al 2002 found that it agonizes one specific ], and that that OR only binds 2-H.<ref name="Liberles-2014">{{cite journal | last=Liberles | first=Stephen D. | title=Mammalian Pheromones | journal=] | publisher=] | volume=76 | issue=1 | date=2014-02-10 | issn=0066-4278 | doi=10.1146/annurev-physiol-021113-170334| pmc=4310675 | pages=151–175| pmid=23988175 }}</ref>

== References ==
{{Reflist}}

== External links ==
*
* , NIOSH Pocket Guide to Chemical Hazards

{{DEFAULTSORT:Heptanone, 2-}}
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