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Saving copy of the {{chembox}} taken from revid 444029078 of page Nonadecylic_acid for the Chem/Drugbox validation project (updated: 'ChEMBL').
 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Nonadecylic_acid|oldid=444029078}} 444029078] of page [[Nonadecylic_acid]] with values updated to verified values.}}
{{Chembox
{{Chembox
| Watchedfields = changed
| verifiedrevid = 444027847
| verifiedrevid =
| Name = Nonadecylic acid
| Name = Nonadecylic acid
| ImageFile = Nonadecylic acid.png
| ImageFile = Nonadecylic acid.
| ImageSize = 250px
| ImageSize = 250px
| ImageFile1 = Nonadecylic-acid-3D-balls.png
| ImageAlt =
| ImageName =
| =
| ImageAlt =
| IUPACName = Nonadecanoic acid
| SystematicName =
| =
| IUPACName = Nonadecanoic acid
| OtherNames =
| SystematicName =
| Section1 = {{Chembox Identifiers
| Abbreviations =
| =
|Section1={{Chembox Identifiers
| CASNo = 646-30-0
| CASNo_Ref =
| =
| CASNo = 646-30-0
| CASNos =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| = {{|correct|}}
| Beilstein = 1786261
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H6M3VYC62P
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12071
| ChemSpiderID = 12071
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
| EC-number = 211-472-4
| = 211-472-4
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ISYWECDDZWTKFF-UHFFFAOYSA-N
| StdInChIKey = ISYWECDDZWTKFF-UHFFFAOYSA-N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1169674
| ChEMBL = 1169674
| PubChem = 12591
| PubChem = 12591
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 39246
| ChEBI = 39246
| SMILES = O=C(O)CCCCCCCCCCCCCCCCCC
| SMILES = O=C(O)CCCCCCCCCCCCCCCCCC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21/h2-18H2,1H3,(H,20,21)
| StdInChI = 1S/C19H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21/h2-18H2,1H3,(H,20,21)
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Appearance = White flakes or powder
| Appearance = White flakes or powder
| BoilingPtC = 236
| BoilingPt = 236°C (10 mmHg) </br> 297°C (100 mmHg)
| = (10 mmHg) <br> 297°C (100 mmHg)
| Density =
| Density =
| Formula = CH<sub>3</sub>(CH<sub>2</sub>)<sub>18</sub>COOH
| Formula = {{chem2|CH3(CH2)17COOH}}
| MolarMass = 298.50382 g/mol
| MolarMass = 298.50382 g/mol
| MeltingPt = 68-70°C
| MeltingPtC = 68 to 70
| Solubility = Insoluble
| SolubleOther =
| =
| Solvent = }}
| =
| SolubleOther =
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| =
|Section7={{Chembox Hazards
| FlashPt =
| LD50 =
| =
| FlashPt =
| MainHazards = Irritant ('''Xi''')
| NFPA-H =
|
NFPA-H =
| NFPA-F =
| NFPA-F =
| NFPA-R =
| NFPA-R =
| NFPA-O =
| NFPA- =
| GHS_ref=<ref>{{cite web |title=Nonadecanoic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/12591#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| RPhrases = {{R36/37/38}}
| SPhrases = {{S26}}
| = {{}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}}
}}
| Section8 = {{Chembox Related
|Section8={{Chembox Related
| Function =
| =
| OtherAnions =
| OtherAnions =
| OtherCations =
| OtherCations =
| OtherCpds =
| =
| OtherFunctn = }}
| =
}}
}}
}}

'''Nonadecylic acid''', or '''nonadecanoic acid''', is a 19-[[carbon]] [[saturated fatty acid]] with the [[chemical formula]] {{chem2|CH3(CH2)17COOH}}. It forms salts called ''nonadecylates''. Nonadecylic acid can be found in [[fat]]s and [[vegetable oil]]s, although it is rare.{{cn|date=April 2023}}

It is also present in the world of [[insect]]s as the major constituent of the substance secreted by soldiers of the [[termite]] ''[[Rhinotermes marginalis]]'' for defence purposes.{{r|Blum}}

Nonadecanoic acid has found applications in the field of metal [[lubrication]].{{r|Smith}}

The compound can be prepared by permanganate oxidation of [[1-Eicosene|1-eicosene]].{{r|OS}}
==See also==
*[[List of saturated fatty acids]]

==References==
{{reflist|refs=
<ref name = "Blum">{{cite journal | vauthors = Blum MS, Jones TH, Howard DF, Overal W | title = Biochemistry of termite defenses: Coptotermes, Rhinotermes and Cornitermes species | date = 1982 | journal = Comparative Biochemistry and Physiology Part B: Comparative Biochemistry | volume = 71 | number = 4 | pages = 731–733 | doi = 10.1016/0305-0491(82)90489-8}}</ref>
<ref name = "Smith">{{cite journal|title=The Adsorption of n-Nonadecanoic Acid on Mechanically Activated Metal Surfaces|journal=The Journal of Physical Chemistry|volume=61|issue=8|pages=1025–1036|doi=10.1021/j150554a001|year=1957|last1=Smith|first1=Hilton A.|last2=McGill|first2=Robert M.}}</ref>
<ref name=OS>{{cite journal|doi=10.15227/orgsyn.060.0011|doi-access=free|first1=Donald G.|last1=Lee|first2=Shannon E. |last2=Lamb|first3=Victor S.|last3=Chang|title=Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid|journal=Organic Syntheses|year=1981|volume=60|page=11}}</ref>
}}

{{Fatty acids}}

[[Category:Fatty acids]]
[[Category:Alkanoic acids]]


{{organic-compound-stub}}