| Revision as of 14:50, 17 February 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors← Previous edit |
Latest revision as of 01:15, 22 July 2022 edit undoHtmlzycq (talk | contribs)Extended confirmed users, IP block exemptions3,941 edits →References |
| (18 intermediate revisions by 13 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{Chembox |
|
{{Chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 414434896 |
|
|
|
| Watchedfields = changed |
|
⚫ |
| verifiedrevid = 414440099 |
|
| ImageFile = Docosanedioic acid.svg |
|
| ImageFile = Docosanedioic acid.svg |
|
| ImageSize = 200px |
|
| ImageSize = |
|
| IUPACName = Docosanedioic acid |
|
| PIN = Docosanedioic acid |
|
| OtherNames = Felogenic acid; Phelogenic acid; Phellogenic acid; 1,22-Docosanedoic acid; 1,20-Eicosanedicarboxylic acid |
|
| OtherNames = Felogenic acid; Phelogenic acid; Phellogenic acid; 1,22-Docosanedoic acid; 1,20-Eicosanedicarboxylic acid |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| InChIKey = |
|
| InChIKey = |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
⚫ |
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
| StdInChI = |
|
| ⚫ |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
| StdInChIKey = |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 505-56-6 |
|
| CASNo = 505-56-6 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| PubChem = |
|
|
|
| UNII = FR7J081T20 |
| ⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
⚫ |
| PubChem = 244872 |
| ⚫ |
| ChemSpiderID = |
|
|
⚫ |
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
| SMILES = OC(CCCCCCCCCCCCCCCCCCCCC(O)=O)=O |
|
|
⚫ |
| ChemSpiderID = 214170 |
|
| InChI = |
|
|
|
| SMILES = C(CCCCCCCCCCC(=O)O)CCCCCCCCCC(=O)O |
|
|
| StdInChI = 1S/C22H42O4/c23-21(24)19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20-22(25)26/h1-20H2,(H,23,24)(H,25,26) |
|
|
| StdInChIKey = DGXRZJSPDXZJFG-UHFFFAOYSA-N |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C=22|H=42|O=4 |
|
| C=22 | H=42 | O=4 |
|
| Appearance = White solid |
|
| Appearance = White solid |
|
| Density = 0.972 g/cm<sup>3</sup> |
|
| Density = 0.972 g/cm<sup>3</sup> |
|
| MeltingPt = 130-131 °C |
|
| MeltingPtC = 119-125 |
|
|
| MeltingPt_ref = <ref>{{Cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/306673 | title = Docosanedioic acid }}</ref> |
|
| BoilingPt = 527 °C |
|
|
| Solubility = Insoluble in water |
|
| BoilingPtC = 527 |
|
|
| Solubility = Insoluble in water |
| ⚫ |
}} |
|
| ⚫ |
| Section3 = {{Chembox Hazards |
|
| ⚫ |
| MainHazards = |
|
| ⚫ |
| FlashPt = 286.6 °C |
|
|
| Autoignition = |
|
|
}} |
|
}} |
|
⚫ |
|Section3={{Chembox Hazards |
|
⚫ |
| MainHazards = |
|
⚫ |
| FlashPtC = 286.6 |
|
|
| AutoignitionPtC = |
|
⚫ |
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Docosanedioic acid''' is a chemical compound with the linear formula HOOC(CH<sub>2</sub>)<sub>20</sub>COOH. |
|
'''Docosanedioic acid''' is a ] with the linear formula {{chem|H|O|O|C|(C|H|2|)|20|C|O|O|H}}. |
|
|
|
|
|
== Uses == |
|
== Uses == |
|
Docosanedioic acid finds uses in organic chemistry and is a starting material for ultrasound contrast agents. It also used to produce the fluffy white solid 1,22-docosanediol which in turn is a precursor to 1,22-bis-2-(trimethylammonium)ethylphospatyldocosane which is a ] derivative with antifungal activity. |
|
Docosanedioic acid finds uses in organic chemistry and is a starting material for ultrasound contrast agents. It is also used to produce the fluffy white solid 1,22-docosanediol, which in turn is a precursor to 1,22-bis-2-(trimethylammonium)ethylphospatyldocosane, a ] derivative with antifungal activity. |
|
|
|
|
|
== Synthesis == |
|
== Synthesis == |
| Line 44: |
Line 49: |
|
Alternately, 2,5-bis(ω-carboyoctyl)thiophene is desulfurized with ] to afford docosanedioic acid. |
|
Alternately, 2,5-bis(ω-carboyoctyl)thiophene is desulfurized with ] to afford docosanedioic acid. |
|
|
|
|
|
Also, oxidative coupling of 10-undecynoic acid to docosa-10,12-diynedoic acid and reduction of this intermediate with a palladium catalyst provides docosanedioic acid. |
|
It can also be produced through oxidative coupling of 10-undecynoic acid to docosa-10,12-diynedoic acid and reduction of this intermediate with a palladium catalyst. |
|
|
|
|
|
== References == |
|
== References == |
|
{{Unreferenced|date=February 2011}} |
|
|
{{Reflist}} |
|
{{Reflist}} |
|
|
{{Navbox linear saturated dicarboxylic acids}} |
|
|
|
|
|
] |
|
] |
|
|
|
|
|
|
|
{{organic-compound-stub}} |
|