Undecylenic acid (CED0010107)

Record Information
Version1.0
Creation Date2014-09-11 05:19:03 UTC
Update Date2026-05-14 19:07:05 UTC
Accession NumberCHEM003803
Identification
Common NameUndecylenic acid
ClassSmall Molecule
Description
Undecylenic acid (C11H20O2) is an exogenous organic compound with an average molecular weight of 184.28 g/mol. It exists as a liquid at room temperature. Undecylenic acid belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. In industrial applications, the compound serves as a surfactant, preservative, emulsifier, cleaning agent, fragrance, and a flavouring and nutrient. It is found in 24 recorded sources, including household cleaning and consumer products such as bleaching agents, ash trays, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. It is also present in electrical and electronic equipment, including electrodes, discharge lamps, coils, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. Within the realm of food, food processing and cookware, it is associated with the preparation of malt, fermentation processes for beer, processing meats, and food preservation. Additionally, it is used in healthcare, pharmaceuticals and veterinary products as an antifungal for dermatological use. Recorded exposure routes for undecylenic acid include topical, cutaneous, and vaginal administration. The compound has two recorded protein targets: the calpain-1 catalytic subunit (CAPN1) and an unknown target of nuclear receptor subfamily 1 group I member 2 (NR1I2).
Contaminant Type
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Synonyms
ValueSource
10-Hendecenoic acidChEBI
10-UndecensaeureChEBI
10-Undecylenic acidChEBI
Acide 10-undecanoiqueChEBI
Acide 10-undecyliqueChEBI
Acido 10-undecenoicoChEBI
Omega-hendecenoic acidChEBI
Omega-undecenoic acidChEBI
Undecelinic acidChEBI
Undecen-10-acid-1ChEBI
Undecen-10-saeureChEBI
Undecenoic acidChEBI
CruexKegg
10-HendecenoateGenerator
10-UndecylenateGenerator
Omega-hendecenoateGenerator
Omega-undecenoateGenerator
UndecelinateGenerator
UndecenoateGenerator
UndecylenateGenerator
10-Undecenoic acidMeSH
MycodermineMeSH
10-HendecenoicHMDB
10-Henedecenoic acidHMDB
9-Undecenoic acidHMDB
9-Undecylenic acidHMDB
DeclidHMDB
DesenexHMDB
FEMA 3247HMDB
N-Undecylenic acidHMDB
N-UNDECYLENIC ACID (10-1)HMDB
RenselinHMDB
SevinonHMDB
Undec-10-enoic acidHMDB
Undecyl-10-enic acidHMDB
Undecylenenic acidHMDB
Undecylenic acid, usanHMDB
Undecylenic acidsHMDB
Zinc undecylenate (undecylenic acid)HMDB
10-UndecenoateHMDB
Undecylenic acidHMDB
ω-Hendecenoic acidHMDB
ω-Undecenoic acidHMDB
Chemical FormulaC11H20O2
Average Molecular Mass184.275 g/mol
Monoisotopic Mass184.146 g/mol
CAS Registry Number112-38-9
IUPAC Nameundec-10-enoic acid
Traditional Namedesenex
SMILESOC(=O)CCCCCCCCC=C
InChI IdentifierInChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)
InChI KeyFRPZMMHWLSIFAZ-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Unsaturated 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point24.5 °C
Boiling PointNot Available
Solubility0.0737 mg/mL at 30 °C
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.84ALOGPS
logP3.73ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)5.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity54.12 m³·mol⁻¹ChemAxon
Polarizability22.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0a6u-9100000000-50cef3280113666a9e23Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a7l-9000000000-830e35fcbdcb4ba9b574Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-056u-9200000000-5b8c18292287532e1debNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00ls-9600000000-b0c6c3ec0da35153ca5dNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a6u-9100000000-50cef3280113666a9e23Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a7l-9000000000-830e35fcbdcb4ba9b574Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-056u-9200000000-5b8c18292287532e1debNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00ls-9600000000-b0c6c3ec0da35153ca5dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00mx-9300000000-c83d63d3e351f1befd83Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-007c-9210000000-1ea20b56f43f28dc1172Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-b90f772663028aa6c273Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0900000000-d8a5d703a9d2aebb6b99Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kr-4900000000-270e01bbabb57dca4ec2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05nf-9100000000-aa66183f7300eea3b4b4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-e0832ba35c6a39bb8de0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00m0-1900000000-7c7091c9da9db8d3bd82Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9300000000-bb79df7af5aab06986f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001j-9500000000-c5d68ca2d338cff02df9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-067i-9000000000-02a41b4e4b35021d18e0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aou-9000000000-459198bd399044a1297fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-d44a0375430320d81c4dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-1900000000-397d0040ec861d2e8403Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pvl-9300000000-7b2ba3000e5fbafc4a58Not AvailableView Spectrum
MSMS Spectrumsplash10-0apl-9100000000-c392a15a3cd57ccae148Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2270.0Log mg/kg[1300:4000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
299Antifungals for dermatological useHealthcare, pharmaceuticals & veterinary productsNot Available
508CoilsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)5.68299
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)7.16213
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)5.60514
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)5.52729
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)4.43741
Fatty acid-binding protein, adipocyte structureClick to view 3D structureFatty acid-binding protein, adipocyteP15090HumansPredicted (SEA)1.94623
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)0.389246
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)10.6653
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)31.8403
Free fatty acid receptor 4 structureClick to view 3D structureFree fatty acid receptor 4Q5NUL3HumansPredicted (SEA)9.18621
Click to view 3D structureCytochrome P450 4A4P10611Oryctolagus cuniculusPredicted (SEA)0.467095
G-protein coupled receptor 84 structureClick to view 3D structureG-protein coupled receptor 84Q9NQS5HumansPredicted (SEA)5.52729
Click to view 3D structureOxoeicosanoid receptor 1Q8TDS5HumansPredicted (SEA)2.33548
Click to view 3D structureCytochrome P450 2C23P24470Rattus norvegicusPredicted (SEA)0.778492
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)87.1133
Fatty acid-binding protein, heart structureClick to view 3D structureFatty acid-binding protein, heartP05413HumansPredicted (SEA)1.47914
Betaine--homocysteine S-methyltransferase 1 structureClick to view 3D structureBetaine--homocysteine S-methyltransferase 1Q93088HumansPredicted (SEA)2.49118
Click to view 3D structureEsteraseA3QR02Chilo suppressalisPredicted (SEA)2.80257
Lysine-specific demethylase 2A structureClick to view 3D structureLysine-specific demethylase 2AQ9Y2K7HumansPredicted (SEA)12.4559
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)65.549
Fatty acid-binding protein 5 structureClick to view 3D structureFatty acid-binding protein 5Q01469HumansPredicted (SEA)2.10193
Click to view 3D structureSeed linoleate 9S-lipoxygenaseP24095Glycine maxPredicted (SEA)1.47914
Click to view 3D structurePhospho-2-dehydro-3-deoxyheptonate aldolaseC3TIE2Escherichia coliPredicted (SEA)0.0778492
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)373.443
Egl nine homolog 1 structureClick to view 3D structureEgl nine homolog 1Q9GZT9HumansPredicted (SEA)32.1517
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDBSALT001514
HMDB IDHMDB0033724
FooDB IDFDB011844
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkUndecylenic_acid
Chemspider ID10771160
ChEBI ID35045
PubChem Compound ID5634
Kegg Compound IDC13910
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19650106
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20270055
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22947450
4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
8. Wilmanski T, Rappaport N, Earls JC, Magis AT, Manor O, Lovejoy J, Omenn GS, Hood L, Gibbons SM, Price ND: Blood metabolome predicts gut microbiome alpha-diversity in humans. Nat Biotechnol. 2019 Oct;37(10):1217-1228. doi: 10.1038/s41587-019-0233-9. Epub 2019 Sep 2.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
10. The lipid handbook with CD-ROM