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Dodecanoic acid (FDB003010)

Record Information
Version1.0
Creation date2010-04-08 22:05:37 UTC
Update date2020-09-17 15:38:38 UTC
Primary IDFDB003010
Secondary Accession Numbers
  • FDB030978
Chemical Information
FooDB NameDodecanoic acid
DescriptionDodecanoic acid also known as Lauric acid, 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. Lauric acid is a weakly acidic compound. It is a white, powdery solid with a faint odour of mild fatty coconut bay oil or soap. Dodecanoic acid is the main fatty acid in coconut oil (49%) and in palm kernel oil (47-50%), and is found in lesser amounts in wild nutmeg, human breast milk, cow’s milk, goat milk, watermelon seeds, plum and macadamia nut ( doi:10.1351/pac200173040685). Dodecanoic acid, although slightly irritating to mucous membranes, has an extremely low toxicity, is inexpensive, has antimicrobial properties and so is used in many soaps and shampoos. It is reacted with sodium hydroxide to generate sodium laurate, which is soap. Dodecanoic acid has been characterized as having "a more favorable effect on total HDL cholesterol than any other fatty acid either saturated or unsaturated" (PMID: 12716665).
CAS Number143-07-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP5.13ALOGPS
logP4.48ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity58.68 m³·mol⁻¹ChemAxon
Polarizability25.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H24O2
IUPAC namedodecanoic acid
InChI IdentifierInChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)
InChI KeyPOULHZVOKOAJMA-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCCCC(O)=O
Average Molecular Weight200.3178
Monoisotopic Molecular Weight200.177630012
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 71.95%; H 12.08%; O 15.97%DFC
Melting PointMp 44°DFC
Boiling PointBp0.65 141-142° (lit. gives a pressure range)DFC
Experimental Water Solubility0.00481 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP4.60SANGSTER (1993)
Experimental pKapKa 5.3 (20°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd20 0.88DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-074l-9100000000-911a01d38925d0de481f2014-09-20View Spectrum
GC-MSDodecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-0910000000-a12b321a54a44ae28972Spectrum
GC-MSDodecanoic acid, 1 TMS, GC-MS Spectrumsplash10-014i-2910000000-d52410168e784872a5a6Spectrum
GC-MSDodecanoic acid, non-derivatized, GC-MS Spectrumsplash10-06xx-9100000000-1ef5cd411f38c53a0a92Spectrum
GC-MSDodecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0706-9100000000-e66a9147257053b93702Spectrum
GC-MSDodecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0706-9100000000-2dd666a9a0355b1ca144Spectrum
GC-MSDodecanoic acid, non-derivatized, GC-MS Spectrumsplash10-074i-9300000000-405ec308fe8c935c62a2Spectrum
GC-MSDodecanoic acid, non-derivatized, GC-MS Spectrumsplash10-067i-0930000000-6a80d41e346f4b10104cSpectrum
GC-MSDodecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-0910000000-a12b321a54a44ae28972Spectrum
GC-MSDodecanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-2910000000-d52410168e784872a5a6Spectrum
GC-MSDodecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-1910000000-8246864bf316bce609a2Spectrum
Predicted GC-MSDodecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9500000000-e05832f94ff0361363a2Spectrum
Predicted GC-MSDodecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g0-9310000000-038e232cccb44582ec9cSpectrum
Predicted GC-MSDodecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDodecanoic 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)splash10-0udi-2290000000-861c4b7b2da35b82ef7f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9100000000-966cf4c6621fcec413682012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-054o-9000000000-d43dd32656ad22e95fdd2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-06xx-9100000000-a71409efaf5fdd6ab0e12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-0706-9100000000-eb09296a8c4c7c381b382012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-f22d8298d64e6f3822792012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-4bb88d3b1d2b7ac881522012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-0900000000-0c79a7257b53685108c62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9600000000-25d268515337ef276c602012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-009b-9000000000-c00963f9b91f4a82e1ef2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-f22d8298d64e6f3822792017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-4bb88d3b1d2b7ac881522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-0c79a7257b53685108c62017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0920000000-63cd88b9477cd281d3422015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5c-4910000000-94738a1f436dcf1abced2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-07ca8cffe5ba2f9f920d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0920000000-63cd88b9477cd281d3422015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5c-4910000000-94738a1f436dcf1abced2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-07ca8cffe5ba2f9f920d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-1655e63166b4d9dd4f592015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-1900000000-7c55a9ca2b49d49200292015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-ed8f6bcf96c68ac847382015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-1655e63166b4d9dd4f592015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-1900000000-7c55a9ca2b49d49200292015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-ed8f6bcf96c68ac847382015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, 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 ID3756
ChEMBL IDNot Available
KEGG Compound IDC02679
Pubchem Compound ID3893
Pubchem Substance IDNot Available
ChEBI ID30805
Phenol-Explorer IDNot Available
DrugBank IDDB03017
HMDB IDHMDB00638
CRC / DFC (Dictionary of Food Compounds) IDCPX59-D:CPX59-D
EAFUS ID1984
Dr. Duke IDDODECANOIC-ACID|LAURIC-ACID
BIGG ID40351
KNApSAcK IDC00001221
HET IDDAO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID143-07-7
GoodScent IDrw1008181
SuperScent IDNot Available
Wikipedia IDDodecanoic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
candidicideDUKE
cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hypercholesterolemicDUKE
Enzymes
NameGene NameUniProt ID
Peroxisomal carnitine O-octanoyltransferaseCROTQ9UKG9
Carnitine O-palmitoyltransferase 2, mitochondrialCPT2P23786
Mitochondrial carnitine/acylcarnitine carrier proteinSLC25A20O43772
S-acyl fatty acid synthase thioesterase, medium chainOLAHQ9NV23
Ganglioside GM2 activatorGM2AP17900
Toll-like receptor 4TLR4O00206
Pathways
NameSMPDB LinkKEGG Link
Beta Oxidation of Very Long Chain Fatty AcidsSMP00052 map01040
Fatty Acid BiosynthesisSMP00456 Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty AcidsSMP00481 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
metal
  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
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coconut
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bay oil
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
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).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— 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.