Pelargonic acid, also called nonanoic acid, is an organic compound with structural formulaCH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in organic solvents. The esters and salts of pelargonic acid are called pelargonates or nonanoates.
Alternatively, pelargonic acid can be produced in a two-step process beginning with coupled dimerization and hydroesterification of 1,3-butadiene. This step produces a doubly unsaturated C9-ester, which can be hydrogenated to give esters of pelargonic acid.[3]
A laboratory preparation involves permanganate oxidation of 1-decene.[4]
Occurrence and usesEdit
Pelargonic acid occurs naturally as esters in the oil of pelargonium.
Synthetic esters of pelargonic acid, such as methyl pelargonate, are used as flavorings. Pelargonic acid is also used in the preparation of plasticizers and lacquers. The derivative 4-nonanoylmorpholine is an ingredient in some pepper sprays. The ammonium salt of pelargonic acid, ammonium pelargonate, is a herbicide. It is commonly used in conjunction with glyphosate, a non-selective herbicide, for a quick burn-down effect in the control of weeds in turfgrass.
Esters of pelargonic acid are precursors to lubricants.
Pharmacological effectsEdit
Pelargonic acid may be more potent than valproic acid in treating seizures.[6] Moreover, in contrast to valproic acid, pelargonic acid exhibited no effect on HDAC inhibition, suggesting that it is unlikely to show HDAC inhibition-related teratogenicity.[6]
^Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
^David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
^Lee, Donald G.; Lamb, Shannon E.; Chang, Victor S. (1981). "Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid". Organic Syntheses. 60: 11. doi:10.15227/orgsyn.060.0011.
^Chitwood, David J. (2002). "Phytochemical Based Strategies for Nematode Control". Annual Review of Phytopathology. Annual Reviews. 40 (1): 221–249. doi:10.1146/annurev.phyto.40.032602.130045. ISSN 0066-4286. PMID 12147760. p.229.
^ abChang, P.; Terbach, N.; Plant, N.; Chen, P. E.; Walker, M. C.; Williams, R. S. (2013). "Seizure control by ketogenic diet-associated medium chain fatty acids". Neuropharmacology. 69: 105–114. doi:10.1016/j.neuropharm.2012.11.004. PMC3625124. PMID 23177536.
External linksEdit
MSDS at affymetrix.com
August 29, 2023
pelargonic, acid, also, called, nonanoic, acid, organic, compound, with, structural, formula, 7co2h, nine, carbon, fatty, acid, nonanoic, acid, colorless, oily, liquid, with, unpleasant, rancid, odor, nearly, insoluble, water, very, soluble, organic, solvents,. Pelargonic acid also called nonanoic acid is an organic compound with structural formula CH3 CH2 7CO2H It is a nine carbon fatty acid Nonanoic acid is a colorless oily liquid with an unpleasant rancid odor It is nearly insoluble in water but very soluble in organic solvents The esters and salts of pelargonic acid are called pelargonates or nonanoates Pelargonic acid NamesPreferred IUPAC name Nonanoic acidOther names Nonoic acid nonylic acid 1 octanecarboxylic acid C9 0 lipid numbers IdentifiersCAS Number 112 05 0 Y3D model JSmol Interactive imageBeilstein Reference 1752351ChEBI CHEBI 29019 YChemSpider 7866 YECHA InfoCard 100 003 574EC Number 203 931 2Gmelin Reference 185341KEGG C01601 YPubChem CID 8158UNII 97SEH7577T YCompTox Dashboard EPA DTXSID3021641InChI InChI 1S C9H18O2 c1 2 3 4 5 6 7 8 9 10 11 h2 8H2 1H3 H 10 11 NKey FBUKVWPVBMHYJY UHFFFAOYSA N NInChI 1 C9H18O2 c1 2 3 4 5 6 7 8 9 10 11 h2 8H2 1H3 H 10 11 Key FBUKVWPVBMHYJY UHFFFAOYAFSMILES CCCCCCCCC O OPropertiesChemical formula C 9H 18O 2Molar mass 158 241 g molAppearance Clear to yellowish oily liquidDensity 0 900 g cm3Melting point 12 5 C 54 5 F 285 6 K Boiling point 254 C 489 F 527 K Critical point T P 439 C 712 K 2 35 MPaSolubility in water 0 3 g LAcidity pKa 4 96 1 1 055 at 2 06 2 63 K 271 09 270 52 C 455 96 454 94 F 1 53 at 191 C 311 8 F 82 1 K Refractive index nD 1 4322HazardsOccupational safety and health OHS OSH Main hazards CorrosiveGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H412Precautionary statements P264 P273 P280 P302 P352 P305 P351 P338 P321 P332 P313 P337 P313 P362 P501NFPA 704 fire diamond 310Flash point 114 C 237 F 387 K Autoignitiontemperature 405 C 761 F 678 K Related compoundsRelated compounds Octanoic acid decanoic acidExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references The acid is named after the pelargonium plant since oil from its leaves contains esters of the acid Contents 1 Preparation 2 Occurrence and uses 3 Pharmacological effects 4 See also 5 References 6 External linksPreparation EditTogether with azelaic acid it is produced industrially by ozonolysis of oleic acid 2 CH 3 CH 2 7 CH CH CH 2 7 CO 2 H 4 O CH 3 CH 2 7 CO 2 H HO 2 C CH 2 7 CO 2 H displaystyle color Red ce CH3 CH2 7CH ce CH CH2 7CO2H 4O longrightarrow color red ce CH3 CH2 7CO2H ce HO2C CH2 7CO2H Alternatively pelargonic acid can be produced in a two step process beginning with coupled dimerization and hydroesterification of 1 3 butadiene This step produces a doubly unsaturated C9 ester which can be hydrogenated to give esters of pelargonic acid 3 2 CH 2 CH CH CH 2 1 3 butadiene CO CH 3 OH CH 2 CH CH 2 3 CH CHCH 2 CO 2 CH 3 displaystyle ce overset 1 3 butadiene 2CH2 CH CH CH2 CO CH3OH gt CH2 CH CH2 3CH CHCH2CO2CH3 CH 2 CH CH 2 3 CH CHCH 2 CO 2 CH 3 2 H 2 CH 3 CH 2 7 CO 2 CH 3 pelargonic acid ester displaystyle ce CH2 CH CH2 3CH CHCH2CO2CH3 2H2 gt underset pelargonic acid ester CH3 CH2 7CO2CH3 A laboratory preparation involves permanganate oxidation of 1 decene 4 Occurrence and uses EditPelargonic acid occurs naturally as esters in the oil of pelargonium Synthetic esters of pelargonic acid such as methyl pelargonate are used as flavorings Pelargonic acid is also used in the preparation of plasticizers and lacquers The derivative 4 nonanoylmorpholine is an ingredient in some pepper sprays The ammonium salt of pelargonic acid ammonium pelargonate is a herbicide It is commonly used in conjunction with glyphosate a non selective herbicide for a quick burn down effect in the control of weeds in turfgrass The methyl form and ethylene glycol pelargonate act as nematicides against Meloidogyne javanica on Solanum lycopersicum and the methyl against Heterodera glycines and M incognita on Glycine max 5 Esters of pelargonic acid are precursors to lubricants Pharmacological effects EditPelargonic acid may be more potent than valproic acid in treating seizures 6 Moreover in contrast to valproic acid pelargonic acid exhibited no effect on HDAC inhibition suggesting that it is unlikely to show HDAC inhibition related teratogenicity 6 See also EditList of saturated fatty acids List of carboxylic acidsReferences Edit Lide D R Ed 1990 CRC Handbook of Chemistry and Physics 70th Edn Boca Raton FL CRC Press David J Anneken Sabine Both Ralf Christoph Georg Fieg Udo Steinberner Alfred Westfechtel Fatty Acids in Ullmann s Encyclopedia of Industrial Chemistry 2006 Wiley VCH Weinheim doi 10 1002 14356007 a10 245 pub2 J Grub E Loser 2012 Butadiene Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a04 431 pub2 Lee Donald G Lamb Shannon E Chang Victor S 1981 Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate Nonadecanoic Acid Organic Syntheses 60 11 doi 10 15227 orgsyn 060 0011 Chitwood David J 2002 Phytochemical Based Strategies for Nematode Control Annual Review of Phytopathology Annual Reviews 40 1 221 249 doi 10 1146 annurev phyto 40 032602 130045 ISSN 0066 4286 PMID 12147760 p 229 a b Chang P Terbach N Plant N Chen P E Walker M C Williams R S 2013 Seizure control by ketogenic diet associated medium chain fatty acids Neuropharmacology 69 105 114 doi 10 1016 j neuropharm 2012 11 004 PMC 3625124 PMID 23177536 External links EditMSDS at affymetrix com Retrieved from https en wikipedia org w index php title Pelargonic acid amp oldid 1171690059, wikipedia, wiki, book, books, library,
