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Nonanoic acid (FDB003306)

Record Information
Version1.0
Creation date2010-04-08 22:05:45 UTC
Update date2020-09-17 15:33:16 UTC
Primary IDFDB003306
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNonanoic acid
DescriptionPelargonic acid, also known as nonanoic acid or pelargon, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Pelargonic acid is an oily liquid with an unpleasant, rancid odor. It is a very hydrophobic molecule, practically insoluble in water but very soluble in organic solvents. The biosynthesis of fatty acid occurs through the acetate pathway and the process is catalyzed by the Fatty Acid Synthase (FAS) enzymes. Structurally, FAS varies significantly across different organisms but essentially, they all perform the same task using the same mechanisms. Nonanoic acid is also used in the preparation of plasticizers and lacquers. Synthetic esters of nonanoic acid, such as methyl nonanoate, are used as flavorings. The derivative 4-nonanoylmorpholine is an ingredient in some pepper sprays. The ammonium salt of nonanoic acid, ammonium nonanoate, is an herbicide. It is commonly used in conjunction with glyphosate, a non-selective herbicide, to control weeds in turfgrass (https://en.wikipedia.org/wiki/Nonanoic_acid). Nonanoic acid may be used to treat seizures (PMID 23177536).
CAS Number112-05-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP3.47ALOGPS
logP3.14ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)5.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity44.88 m³·mol⁻¹ChemAxon
Polarizability19.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H18O2
IUPAC namenonanoic acid
InChI IdentifierInChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)
InChI KeyFBUKVWPVBMHYJY-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCC(O)=O
Average Molecular Weight158.238
Monoisotopic Molecular Weight158.13067982
Classification
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 68.31%; H 11.46%; O 20.22%DFC
Melting PointFp 12.24°DFC
Boiling PointBp1 98.9°DFC
Experimental Water Solubility0.284 mg/mL at 20 oCRIDDICK,JA et al. (1986)
Experimental logP3.42SANGSTER (1993)
Experimental pKapKa 4.95DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.91DFC
Refractive Indexn20D 1.4309DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-08ml-9000000000-e02b73fd7a397aa0b40b2014-09-20View Spectrum
GC-MSNonanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0910000000-29827f2f9240f991b625Spectrum
GC-MSNonanoic acid, 1 TMS, GC-MS Spectrumsplash10-014i-2920000000-8730f6690cd20a58fcfcSpectrum
GC-MSNonanoic acid, non-derivatized, GC-MS Spectrumsplash10-03di-9200000000-0842bd1d3fcea3f9f005Spectrum
GC-MSNonanoic acid, non-derivatized, GC-MS Spectrumsplash10-08ml-9000000000-f9b45b786372be8b75d6Spectrum
GC-MSNonanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0930000000-30578d3edfa20cedf0e8Spectrum
GC-MSNonanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0910000000-29827f2f9240f991b625Spectrum
GC-MSNonanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-2920000000-8730f6690cd20a58fcfcSpectrum
GC-MSNonanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0910000000-2e292fa3a6e414ce582aSpectrum
Predicted GC-MSNonanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-059f-9100000000-aaba2a9436e55f8d4c46Spectrum
Predicted GC-MSNonanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06du-9200000000-bffc58a95ef321200ab9Spectrum
Predicted GC-MSNonanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNonanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNonanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0k9l-9400000000-fb4f24d4e9b0b46857632012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-a3d26c56923a3cdddf9c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-a6e0c758ef2e822a5d732012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03di-9200000000-0842bd1d3fcea3f9f0052012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-08ml-9000000000-141c2435131c4b2353902012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0900000000-2ea046a2e7b029c3cd812012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-0900000000-1efff6d47779ec04f4342012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-6900000000-bcf3e35c2fbd86e670f02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9000000000-9c72ae1d7f8e978ec7f82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-c052a9b360e11f6a6eb92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-2ea046a2e7b029c3cd812017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-1efff6d47779ec04f4342017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-6900000000-bcf3e35c2fbd86e670f02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9000000000-9c72ae1d7f8e978ec7f82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-c052a9b360e11f6a6eb92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0a4i-0900000000-b56762cc671f243abe6f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014r-9000000000-ae54c10a9e1b7264831e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-052r-9500000000-65dcbde71c36004a36762021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8ddcc5d65e84f9048b882021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-2b95d53127d2c88c6b0c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-6900000000-e3f666b3dcf9b3b1c2fe2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-8432ab96716adadb8d132015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-32f3915adea9c27b0b742015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-1900000000-2ffdf4f1d36a54e86be12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-647e33e0c7198b77f78b2015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID7866
ChEMBL IDCHEMBL108436
KEGG Compound IDC01601
Pubchem Compound ID8158
Pubchem Substance IDNot Available
ChEBI ID29019
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00847
CRC / DFC (Dictionary of Food Compounds) IDCVW57-M:CVW57-M
EAFUS ID2692
Dr. Duke IDPELARGONIC-ACID|NONANOIC-ACID|N-NONANOIC-ACID
BIGG IDNot Available
KNApSAcK IDC00030829
HET IDKNA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID112-05-0
GoodScent IDrw1012131
SuperScent IDNot Available
Wikipedia IDNonanoic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
green
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fat
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
waxy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dirty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cheese
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cultured dairy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.