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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:41:55 UTC
NP-MRD IDNP0001225
Secondary Accession NumbersNone
Natural Product Identification
Common NameDodecanoic acid
DescriptionLauric acid, or dodecanoic acid is the main fatty acid in coconut oil and in palm kernel oil, and is believed to have antimicrobial properties. It is a white, powdery solid with a faint odor of bay oil. Lauric acid, although slightly irritating to mucous membranes, has a very low toxicity and so is used in many soaps and shampoos.
Structure
Thumb
Synonyms
ValueSource
1-Undecanecarboxylic acidChEBI
ABLChEBI
C12 Fatty acidChEBI
C12:0ChEBI
CH3-[CH2]10-COOHChEBI
Coconut oil fatty acidsChEBI
DAOChEBI
Dodecoic acidChEBI
DodecylcarboxylateChEBI
Dodecylic acidChEBI
Duodecyclic acidChEBI
Duodecylic acidChEBI
Lauric acidChEBI
LaurinsaeureChEBI
Laurostearic acidChEBI
N-Dodecanoic acidChEBI
Undecane-1-carboxylic acidChEBI
Vulvic acidChEBI
DodecanoateKegg
1-UndecanecarboxylateGenerator
DodecoateGenerator
Dodecylcarboxylic acidGenerator
DodecylateGenerator
DuodecyclateGenerator
DuodecylateGenerator
LaateGenerator
Laic acidGenerator
LaurostearateGenerator
N-DodecanoateGenerator
Undecane-1-carboxylateGenerator
VulvateGenerator
Aliphat no. 4HMDB
Edenor C 1298-100HMDB
Emery 651HMDB
Hystrene 9512HMDB
Kortacid 1299HMDB
LaurateHMDB
Lunac L 70HMDB
Lunac L 98HMDB
Neo-fat 12HMDB
Neo-fat 12-43HMDB
Nissan naa 122HMDB
Philacid 1200HMDB
Prifac 2920HMDB
Univol u 314HMDB
1-Dodecanoic acidHMDB
FA(12:0)HMDB
Dodecanoic acidPhytoBank
Chemical FormulaC12H24O2
Average Mass200.3178 Da
Monoisotopic Mass200.17763 Da
IUPAC Namedodecanoic acid
Traditional Namelauric acid
CAS Registry Number143-07-7
SMILES
CCCCCCCCCCCC(O)=O
InChI Identifier
InChI=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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
Allium cepa L.FooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Aloe vera var.chinensisKNApSAcK Database
AmaranthusFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
AnatidaeFooDB
Anethum graveolensFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Anthemis aciphylla BOISS.var.discoidea BOISSKNApSAcK Database
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Areca catechuKNApSAcK Database
Armoracia rusticanaFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Belone beloneFooDB
Bertholletia excelsaFooDB
Beta vulgaris ssp. ciclaFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
BrachyuraFooDB
Brassica hirtaKNApSAcK Database
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. rapaFooDB
Cancer magisterFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Carica papaya L.FooDB
CarideaFooDB
Carthamus tinctoriusKNApSAcK Database
Carum carviFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Cedrus libaniKNApSAcK Database
Celosia cristadaKNApSAcK Database
Centaurea atropurpureaKNApSAcK Database
Ceratonia siliquaFooDB
CervidaeFooDB
Chenopodium quinoaFooDB
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus limonFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
ClupeinaeFooDB
Cocos nuciferaKNApSAcK Database
Codonopsis pilosulaKNApSAcK Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
ColumbidaeFooDB
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Crassostrea gigasFooDB
Crassostrea virginicaFooDB
Crocus sativusFooDB
Croton tigliumKNApSAcK Database
Cucumis meloFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cuphea carthagenensisKNApSAcK Database
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
DioscoreaFooDB
DiospyrosFooDB
Drymaria cordataKNApSAcK Database
ElaeisFooDB
Elaeis guineensisKNApSAcK Database
Elettaria cardamomumFooDB
EngraulidaeFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Esox luciusFooDB
EucheumaFooDB
Fagopyrum esculentumFooDB
Ficus caricaFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gallus gallusFooDB
GastropodaFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippophae rhamnoidesKNApSAcK Database
Holoptelea integrifoliaKNApSAcK Database
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Ictalurus punctatusFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans nigra L.FooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagopus mutaFooDB
Lantana camaraKNApSAcK Database
Laurus nobilisKNApSAcK Database
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lota lotaFooDB
Lupinus albusFooDB
MacadamiaFooDB
MalusFooDB
Malus pumilaFooDB
Mandragora autumnalisKNApSAcK Database
Mangifera indicaFooDB
Manihot esculentaFooDB
Medicago sativaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Merlangius merlangusFooDB
Micromesistius poutassouFooDB
Microstomus kittFooDB
Molva molvaFooDB
Momordica charantiaFooDB
Musa x paradisiacaFooDB
Myristica fragransFooDB
MytilidaeFooDB
Neolitsea aciculataKNApSAcK Database
Neolitsea sericeaKNApSAcK Database
NephropidaeFooDB
Nephrops norvegicusFooDB
Nigella sativa LKNApSAcK Database
Nuphar luteaFooDB
Octopus vulgarisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
OpuntiaFooDB
Origanum vulgareFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Ovis ariesFooDB
Panicum miliaceumFooDB
PapaverFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PectinidaeFooDB
PerciformesFooDB
Persea americanaFooDB
Petasites hybridusKNApSAcK Database
Petroselinum crispumFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phoenix dactyliferaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
PinusFooDB
Pinus sibiricaKNApSAcK Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
PollachiusFooDB
Polygonum minusKNApSAcK Database
Prunus armeniacaFooDB
Prunus avium L.FooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Psidium guajavaFooDB
Punica granatumKNApSAcK Database
Pyrus communisFooDB
RanidaeFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Rehmannia glutinosaKNApSAcK Database
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Rhodiola rosea L.KNApSAcK Database
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubia wallichiana DECNEKNApSAcK Database
Rumex acetosaFooDB
Saccharina japonicaFooDB
Salmo salarFooDB
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Santalum albumKNApSAcK Database
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
SiluriformesFooDB
Sinapis albaFooDB
Solanum lycopersicumFooDB
Solanum melongenaFooDB
Solanum tuberosumKNApSAcK Database
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Stenodus leucichthysFooDB
StrombidaeFooDB
Sus scrofa domesticaFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
ThunnusFooDB
Thunnus albacaresFooDB
Thymus vulgarisFooDB
Trichosanthes kirilowiiKNApSAcK Database
Trichosanthes rosthorniiKNApSAcK Database
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivumKNApSAcK Database
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
VacciniumFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtillusFooDB
Vaccinium vitis-idaeaFooDB
VanillaFooDB
Vicia fabaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Virola surinamensisFooDB
VitisFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Species Where Detected
Species NameSourceReference
Acantophora spiciferaKNApSAcK Database
Ganoderma lucidumKNApSAcK Database
Homo sapiens (Skin)KNApSAcK Database
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
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point44 - 46 °CNot Available
Boiling Point225.00 °C. @ 100.00 mm HgThe Good Scents Company Information System
Water Solubility0.0048 mg/mLNot Available
LogP4.60Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP10(5.13) g/LALOGPS
logP10(4.48) g/LChemAxon
logS10(-4.3) g/LALOGPS
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
HMDB IDHMDB0000638
DrugBank IDDB03017
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030978
KNApSAcK IDC00001221
Chemspider ID3756
KEGG Compound IDC02679
BioCyc IDDODECANOATE
BiGG ID40351
Wikipedia LinkLauric_acid
METLIN ID5611
PubChem Compound3893
PDB IDNot Available
ChEBI ID30805
Good Scents IDrw1008181
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  3. Amet Y, Berthou F, Fournier G, Dreano Y, Bardou L, Cledes J, Menez JF: Cytochrome P450 4A and 2E1 expression in human kidney microsomes. Biochem Pharmacol. 1997 Mar 21;53(6):765-71. [PubMed:9113097 ]
  4. Smith SW, Anderson BD: Human skin permeability enhancement by lauric acid under equilibrium aqueous conditions. J Pharm Sci. 1995 May;84(5):551-6. [PubMed:7658343 ]
  5. Powell PK, Wolf I, Lasker JM: Identification of CYP4A11 as the major lauric acid omega-hydroxylase in human liver microsomes. Arch Biochem Biophys. 1996 Nov 1;335(1):219-26. [PubMed:8914854 ]
  6. Ryan MT, Chopra RK: The paradoxical effect of fatty acid on steroid-albumin interaction. Biochim Biophys Acta. 1976 Mar 18;427(1):337-49. [PubMed:1260006 ]
  7. Amet Y, Berthou F, Baird S, Dreano Y, Bail JP, Menez JF: Validation of the (omega-1)-hydroxylation of lauric acid as an in vitro substrate probe for human liver CYP2E1. Biochem Pharmacol. 1995 Nov 27;50(11):1775-82. [PubMed:8615855 ]
  8. Kitahara T, Koyama N, Matsuda J, Aoyama Y, Hirakata Y, Kamihira S, Kohno S, Nakashima M, Sasaki H: Antimicrobial activity of saturated fatty acids and fatty amines against methicillin-resistant Staphylococcus aureus. Biol Pharm Bull. 2004 Sep;27(9):1321-6. [PubMed:15340213 ]
  9. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Lauric Acid Diethanolamine Condensate (CAS NO. 120-40-1) in F344/N Rats and B6C3F1 Mice (Dermal Studies). Natl Toxicol Program Tech Rep Ser. 1999 Jul;480:1-200. [PubMed:12571683 ]
  10. Amet Y, Berthou F, Menez JF: Simultaneous radiometric and fluorimetric detection of lauric acid metabolites using high-performance liquid chromatography following esterification with 4-bromomethyl-6,7-dimethoxycoumarin in human and rat liver microsomes. J Chromatogr B Biomed Appl. 1996 Jun 7;681(2):233-9. [PubMed:8811432 ]