Pimelic acid: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid =

| Name = Pimelic acid

| = Pimelic acid

| ImageSize =

| ImageAlt = Skeletal formula of pimelic acid

| ImageFile1 = Pimelicacid.png

| ImageSize1 =

| ImageAlt1 = Ball-and-stick model of the pimelic acid molecule

| PIN = Heptanedioic acid

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite}}

| UNII_Ref = {{fdacite|correct|FDA}}

| 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

| Formula = C₇H₁₂O₄

| Appearance = colorless or white solid

| = . g/

| Density = 1.28 g/cm³

| MeltingPtC = 103 to 105

| MeltingPt_notes =

| BoilingPt =

| = 4.71 pKa2 = 5.58 <>CRC Handbook of and Physics 83rd ed. p.8-52

'''Pimelic acid''' is the [[organic compound]] with the [[chemical formula|formula]] HO₂C(CH₂)₅CO₂H. Pimelic acid is one [[methylene]] longer than a related [[dicarboxylic acid]], adipic acid, a precursor to many polyesters and polyamides. of [[ ]]

== Synthesis ==

===Biosynthesis===

The biosynthesis of pimelic acid is unknown but is speculated to start with [[malonyl CoA]].<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===

Like other simple [[dicarboxylic acid]]s, many methods have been developed for producing pimelic acid.

Pimelic acid is produced commercially by oxidation of [[cycloheptanone]] with [[dinitrogen tetroxide]]. Other routes include the relatively unselective oxidation of palmitic acid and the [[carbonylation]] of [[caprolactone]].<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 [[cyclohexanone]] and from [[salicylic acid]].<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[[oxalate]], 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 [[acrolein]].<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==

{{Navbox linear saturated dicarboxylic acids}}

{{Authority control}}

[[Category:Dicarboxylic acids]]