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	{{chembox		{{chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 292788055		| verifiedrevid = 447493998
	| Name = Pimelic acid		| Name = Pimelic acid
	| ImageFile = Pimelic acid.png		| ImageFile = Pimelic acid.png
	<!-- | ImageSize = 200px -->		| ImageSize = 240
	| ImageName = Pimelic acid		| ImageAlt = Skeletal formula of pimelic acid
	| ImageFile1 = Pimelic-acid-3D-balls.png		| ImageFile1 = Pimelic acid molecule ball from xtal.png
	| ImageSize1 = 230px		| ImageSize1 = 240
			| ImageAlt1 = Ball-and-stick model of the pimelic acid molecule
	| IUPACName = heptanedioic acid
			| PIN = Heptanedioic acid
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo_Ref = {{cascite}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 111-16-0		| CASNo = 111-16-0
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| SMILES = OC(=O)CCCCCC(=O)O
			| UNII = BZQ96WX25F
		⚫	| SMILES = OC(=O)CCCCCC(=O)O
			| EINECS = 203-840-8
			| PubChem = 385
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 376
			| InChI = 1/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)
			| InChIKey = WLJVNTCWHIRURA-UHFFFAOYAR
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = WLJVNTCWHIRURA-UHFFFAOYSA-N
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 30531
			| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
			| DrugBank = DB01856
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>7</sub>H<sub>12</sub>O<sub>4</sub>		| Formula = C<sub>7</sub>H<sub>12</sub>O<sub>4</sub>
			| Appearance = colorless or white solid
	| MolarMass = 160.17 g/mol
	| Density = 1.28 g/cm<sup>3</sup>		| MolarMass = 160.17 g/mol
			| Density = 1.28 g/cm<sup>3</sup>
	| MeltingPt = 103-105 °C
			| MeltingPtC = 103 to 105
⚫	| BoilingPt = Decomposes
			| MeltingPt_notes =
⚫	| pKa1 = 4.71 pKa2 = 5.58 <references/>CRC Handbook of Chemcistry and Physics 83rd ed. p.8-52
		⚫	| BoilingPt = decomposes
	| pKa1 = 4.71 pKa2 = 5.58 </ref>CRC Handbook of Chemistry and Physics 83rd ed. p.8-52
		⚫	| pKa = 4.71 pKa2 = 5.58 <ref>CRC Handbook of Chemistry and Physics 83rd ed. p.8-52</ref>
	}}		}}
	}}		}}
	'''Pimelic acid''' is the ] with the ] HO<sub>2</sub>C(CH<sub>2</sub>)<sub>5</sub>CO<sub>2</sub>H. Derivatives of pimelic acid are involved in the biosynthesis of the ] called ]. Pimelic acid is one methylene longer than a related ], adipic acid, a precursor to many polyesters and polyamides. It is the final member of the mnemonic used to aid recollection of the order of the first six dicarboxylic acids using their common (not IUPAC) nomenclature: ]		'''Pimelic acid''' is the ] with the ] HO<sub>2</sub>C(CH<sub>2</sub>)<sub>5</sub>CO<sub>2</sub>H. Pimelic acid is one ] longer than a related ], ], a precursor to many polyesters and polyamides. However compared to adipic acid, pimelic acid is relatively small in importance industrially.<ref name=Ullmann/> Derivatives of pimelic acid are involved in the biosynthesis of the ] ] and the vitamin ].
			== Synthesis ==
	Pimelic acid has been synthesized from ] and from ].<ref>Snyder, H. R.; Brooks, A. L.; Shapiro, S. H. "Pimelic Acid from Cyclohexanone" and Müller, A. "Pimelic Acid from Salicylic Acid"
			===Biosynthesis===
	Organic Syntheses, Collected Volume 2, p.531 (1943).http://www.orgsyn.org/orgsyn/pdfs/CV2P0531.pdf</ref> In the former route, the additional carbon is supplied by dimethyl], which reacts with the enolate.
			The biosynthesis of pimelic acid is unknown but is speculated to start with ].<ref>{{cite journal |doi=10.1111/mmi.13648|title=Pimelic Acid, the First Precursor of the ''Bacillus subtilis'' Biotin Synthesis Pathway, Exists as the Free Acid and Is Assembled by Fatty Acid Synthesis|year=2017|last1=Manandhar|first1=Miglena|last2=Cronan|first2=John E.|journal=Molecular Microbiology|volume=104|issue=4|pages=595–607|pmid=28196402 |s2cid=13732917|pmc=5426962}}</ref>
			===Chemical and industrial routes===
⚫	==See also==
			Like other simple ]s, many methods have been developed for producing pimelic acid.
			Pimelic acid is produced commercially by oxidation of ] with ]. Other routes include the relatively unselective oxidation of ] and the ] of ].<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a08_523|chapter=Dicarboxylic Acids, Aliphatic|year=2000|last1=Cornils|first1=Boy|last2=Lappe|first2=Peter}}</ref>
			====Niche methods====
			Many other methods exist. Pimelic acid has been synthesized from ] and from ].<ref>{{cite journal|author=H. R. Snyder |author2=L. A. Brooks |author3=S. H. Shapiro |author4=A. Müller |title=Pimelic Acid|journal=Organic Syntheses|volume=11|page=42|year=1931|doi=10.15227/orgsyn.011.0042}}</ref> In the former route, the additional carbon is supplied by dimethyl], which reacts with the enolate.
			In other syntheses, pimelic acid is made from cyclohexene-4-carboxylic acid,<ref>{{cite journal|doi=10.1021/ja01122a075|title=The Synthesis of Pimelic Acid from Cyclohexene-4-carboxylic Acid and its Derivatives|journal=Journal of the American Chemical Society|volume=74|issue=2|page=532|year=1952|last1=Werber|first1=Frank X.|last2=Jansen|first2=J. E.|last3=Gresham|first3=T. L.}}</ref> and a fourth method also exists based on the 1,4 reaction of malonate systems with ].<ref>{{cite journal|doi=10.1021/ja01122a024|title=Synthesis of Pimelic Acid and α-Substituted Pimelic Acid and Intermediates1|journal=Journal of the American Chemical Society|volume=74|issue=2|page=371|year=1952|last1=Warner|first1=Donald T.|last2=Moe|first2=Owen A.}}</ref>
			Several patents exist for the production of pimelic acid.<ref>{{US patent|2826609}}</ref><ref>{{US patent|2800507}}</ref><ref>{{US patent|2698339}}</ref><ref>{{US patent|3468927}}</ref><ref>{{US patent|4888443}}</ref><ref>{{US patent|2673219}}</ref>
		⚫	== See also ==
	* ]		* ]
	==References==		== References ==
	{{reflist}}		{{reflist}}
			{{Navbox linear saturated dicarboxylic acids}}
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