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			{{short description|Alpha-beta unsaturated cyclic ketone}}
			{{About|α-isophorone|its isomer|β-isophorone}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 415669608		| verifiedrevid = 443979911
	| Name = Isophorone		| Name = Isophorone
	| Reference =<ref>''Merck Index'', 13th Edition, '''5215'''.</ref>		| Reference =<ref>'']'', 13th Edition, '''5215'''.</ref>
	| ImageFile_Ref = {{chemboximage|correct|??}}		| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile = Isophorone.png		| ImageFile = Isophorone.png
	<!-- | ImageSize = 120px -->		| ImageSize = 120px
	| ImageName = Isophorone		| ImageName = Isophorone
	| IUPACName = 3,5,5-Trimethyl-2-cyclohexen-1-one		| PIN = 3,5,5-Trimethylcyclohex-2-en-1-one
	| OtherNames = 1,1,3-Trimethyl-3-cyclohexene-5-one<br />Isoforone<br />Isoacetophorone		| OtherNames = 3,5,5-Trimethyl-2-cyclohexene-1-one<br />1,1,3-Trimethyl-3-cyclohexene-5-one<br />Isoforone<br />Isoacetophorone<br />IP
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6296		| ChemSpiderID = 6296
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
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	| StdInChIKey = HJOVHMDZYOCNQW-UHFFFAOYSA-N		| StdInChIKey = HJOVHMDZYOCNQW-UHFFFAOYSA-N
	| CASNo = 78-59-1		| CASNo = 78-59-1
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem = 6544
			| UNII = 2BR99VR6WA
⚫	| SMILES = O=C1\C=C(/CC(C)(C)C1)C
		⚫	| PubChem = 6544
		⚫	| SMILES = O=C1\C=C(/CC(C)(C)C1)C
			| EINECS = 201-126-0
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=9 | H=14 | O=1
	| Formula = C<sub>9</sub>H<sub>14</sub>O
	| MolarMass = 138.21 g/mol		| Density = 0.9255 g/cm<sup>3</sup>
			| Appearance = Colorless to white liquid
	| Density = 0.92 g/cm<sup>3</sup>
			| Odor = Peppermint-like<ref name=PGCH/>
	| MeltingPt = -8.1 °C
	| BoilingPt = 215.2 °C		| MeltingPtC = -8.1
			| BoilingPtC = 215.32
			| Solubility = 1.2 g/100 mL
			| SolubleOther = ], ], ], ], ], ], ]
			| RefractIndex = 1.4766
			| Viscosity = 2.62 cP
			| VaporPressure = 0.3 mmHg (20°C)<ref name=PGCH/>
			}}
			|Section4={{Chembox Thermochemistry
			| DeltaHf = 43.4 kJ/mol
			}}
			|Section7={{Chembox Hazards
			| FlashPtC = 84
			| AutoignitionPtC = 460
			| LD50 = 2280 mg/kg (rat, oral){{citation needed|date=July 2015}}<br/>2330 mg/kg (rat, oral)<br/>2690 mg/kg (mouse, oral)<ref name=IDLH/>
			| IDLH = 200 ppm<ref name=PGCH>{{PGCH|0355}}</ref>
			| REL = TWA 4 ppm (23 mg/m<sup>3</sup>)<ref name=PGCH/>
			| PEL = TWA 25 ppm (140 mg/m<sup>3</sup>)<ref name=PGCH/>
			| ExploLimits = 0.8–3.8%<ref name=PGCH/>
			| LC50 = 4600 ppm (guinea pig, 8 hr)<ref name=IDLH>{{IDLH|78591|Isophorone}}</ref>
			| LCLo = 885 ppm (rat, 6 hr)<br/>1840 ppm (rat, 4 hr)<ref name=IDLH/>
	}}		}}
	}}		}}
	''' Isophorone''' is an ], a colorless to yellowish liquid with characteristic smell, that is used as a ] and as an intermediate in ]. Isophorone also occurs naturally in ].<ref name="oehha"> </ref>		'''Isophorone''' is an ]. It is a colorless liquid with a characteristic peppermint-like odor, although commercial samples can appear yellowish. Used as a ] and as a precursor to polymers, it is produced on a large scale industrially.<ref name=Ullmann>{{cite encyclopedia|author=Hardo Siegel |author2=Manfred Eggersdorfer |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a15_077|isbn=978-3-527-30673-2|chapter=Ketones}}</ref>
			== Structure and reactivity ==
	==Production==
			Isophorone undergoes reactions characteristic of an α,β-unsaturated ketone. Hydrogenation gives the cyclohexanone derivative. Epoxidation with basic ] affords the oxide.<ref>{{cite journal|title=Isophorone Oxide|author=Richard L. Wasson |author2=Herbert O. House |journal=Org. Synth.|year=1957|volume=37|page=58|doi= 10.15227/orgsyn.037.0058}}</ref>
	Isophorone can be manufactured by catalyzed ] of ].<ref> {{US patent|5849957}}</ref>
	] is the initial product of the self-aldol condensation of acetone. The ] formed can react further with acetone via a ] and subsequent intramolecular aldol condensation to eventually obtain the six-membered ring of isophorone. This is an example of the ]. The yield of the two compounds depends on the reaction conditions.
			Isophorone is degraded by attack of ]s.<ref name=":0">{{Cite web|url = http://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+@rel+78-59-1|archive-url = https://web.archive.org/web/20171024043320/https://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+@rel+78-59-1|archive-date = 2017-10-24|title = TOXNET|website = toxnet.nlm.nih.gov|access-date = 2016-03-11}}</ref>
	:]
			===Photodimerization===
⚫	==History==
			When exposed to sunlight in aqueous solutions, isophorone undergoes ] to give three isomeric photodimers (Figure). These "diketomers" are cis-syn-cis, head to tail (HT), cys-anti-cys (HT), and head-head (HH). The formation of HH photodimers is favored over HT photodimers with increasing polarity of the medium.<ref name="Gonçalves 1279–1287">{{Cite journal|last1=Gonçalves|first1=Huguette|last2=Robinet|first2=Germaine|last3=Barthelat|first3=Michèle|last4=Lattes|first4=Armand|date=1998-01-28|title=Supramolecularity and Photodimerization of Isophorone: FTIR and Molecular Mechanics Studies|journal=The Journal of Physical Chemistry A|language=en|volume=102|issue=8|pages=1279–1287|doi=10.1021/jp9729270|bibcode=1998JPCA..102.1279G }}</ref>
⚫	The use of isophorone as a solvent resulted from the search for ways to dispose of or recycle ], which is a waste product of ] synthesis by the ].<ref> </ref>
			]
	==Uses==
	Isophorone is used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticides.<ref name="oehha"/> It is also used as a chemical intermediate and as an ingredient in wood preservatives and floor sealants.
			== Natural occurrence ==
			Isophorone occurs naturally in ].<ref name="PubChem">{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/Isophorone|title=Isophorone}}</ref>
			== Synthesis ==
			Isophorone is produced on a multi-thousand ton scale by the ] of ] using KOH. ], ], and 3-hydroxy-3,5,5-trimethylcyclohexan-1-one are intermediates. A side product is ], where the C=C group is not conjugated with the ketone.<ref name=Ullmann/>
			]
			==Applications==
			The partly hydrogenated derivative trimethylcyclohexanone is used in production of ]s. It condenses with phenol to give an analogue of ]. Polycarbonates produced by phosgenation of these two diols produces a polymer with improved thermal stability.<ref name=UllmannPoly>{{cite encyclopedia|author=Volker Serini |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2000|doi=10.1002/14356007.a21_207|isbn=978-3-527-30673-2|chapter=Polycarbonates}}</ref> Trimethyl] and ] are produced from trimethylcyclohexanone and trimethylcyclohexanol. They are used to make specialty ]s. Hydrocyanation gives the nitrile followed by reductive amination gives ]. This diamine is used to produce ] which has certain niche applications.<ref name=Ullmann/>
			] is used to produce specialty ]s.]]
			Full hydrogenation gives ], a precursor to both sunscreens and chemical weapons.
			==Safety==
			The {{LD50}} value of isophorone in rats and rabbits by oral exposure is around 2.00 g/kg.<ref name=":2">{{Cite web|url=http://tools.niehs.nih.gov/cebs3/ntpviews/index.cfm?action=testarticle.toxicity&cas_number=389-08-2|title=Toxicity Effects|website=tools.niehs.nih.gov|access-date=2016-03-11}}</ref> The safety aspects of isophorone have been subject to several studies.<ref name=":6">{{Cite journal|last=W. Morton Grant, Joel S. Schuman M.D|date=11 February 2016|title=Toxicology of the Eye: Effects on the Eyes and Visual System from Chemicals, Drugs, Metals and Minerals, Plants, Toxins, and Venoms; Also, Systemic Side Effects from Eye|journal=Med (2-Volume Set) 4th Edition, Page 863}}</ref>
		⚫	==History==
		⚫	The use of isophorone as a solvent resulted from the search for ways to dispose of or recycle ], which is a waste product of ] synthesis by the ].<ref></ref>
	==See also==		==See also==
	*]		*]
			*]
	==References==		==References==
			{{Reflist}}
	<references/>
			{{Authority control}}
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