Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:34:04 UTC |
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Update Date | 2020-06-04 22:49:43 UTC |
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BMDB ID | BMDB0000638 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dodecanoic acid |
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Description | Dodecanoic acid, also known as dodecanoate or potassium laurate, 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. Dodecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Dodecanoic acid exists in all living species, ranging from bacteria to humans. Dodecanoic acid participates in a number of enzymatic reactions, within cattle. In particular, Dodecanoic acid and coenzyme A can be converted into lauroyl-CoA and L-carnitine; which is catalyzed by the enzyme carnitine O-palmitoyltransferase 2, mitochondrial. In addition, Dodecanoic acid can be converted into dodecanoic acid; which is catalyzed by the enzyme peroxisomal membrane protein 11C. In cattle, dodecanoic acid is involved in the metabolic pathway called the Beta oxidation OF very long chain fatty acids pathway. Dodecanoic acid is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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1-Undecanecarboxylic acid | ChEBI | ABL | ChEBI | C12 Fatty acid | ChEBI | C12:0 | ChEBI | CH3-[CH2]10-COOH | ChEBI | Coconut oil fatty acids | ChEBI | DAO | ChEBI | Dodecoic acid | ChEBI | Dodecylcarboxylate | ChEBI | Dodecylic acid | ChEBI | Duodecyclic acid | ChEBI | Duodecylic acid | ChEBI | Lauric acid | ChEBI | Laurinsaeure | ChEBI | Laurostearic acid | ChEBI | N-Dodecanoic acid | ChEBI | Undecane-1-carboxylic acid | ChEBI | Vulvic acid | ChEBI | Dodecanoate | Kegg | 1-Undecanecarboxylate | Generator | Dodecoate | Generator | Dodecylcarboxylic acid | Generator | Dodecylate | Generator | Duodecyclate | Generator | Duodecylate | Generator | Laate | Generator | Laic acid | Generator | Laurostearate | Generator | N-Dodecanoate | Generator | Undecane-1-carboxylate | Generator | Vulvate | Generator | Aliphat no. 4 | HMDB | Edenor C 1298-100 | HMDB | Emery 651 | HMDB | Hystrene 9512 | HMDB | Kortacid 1299 | HMDB | Laurate | HMDB | Lunac L 70 | HMDB | Lunac L 98 | HMDB | Neo-fat 12 | HMDB | Neo-fat 12-43 | HMDB | Nissan naa 122 | HMDB | Philacid 1200 | HMDB | Prifac 2920 | HMDB | Univol u 314 | HMDB | 1-Dodecanoic acid | HMDB | FA(12:0) | HMDB | Dodecanoic acid | PhytoBank |
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Chemical Formula | C12H24O2 |
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Average Molecular Weight | 200.3178 |
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Monoisotopic Molecular Weight | 200.177630012 |
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IUPAC Name | dodecanoic acid |
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Traditional Name | lauric acid |
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CAS Registry Number | 143-07-7 |
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SMILES | CCCCCCCCCCCC(O)=O |
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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) |
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InChI Key | POULHZVOKOAJMA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Medium-chain fatty acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 44 - 46 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.00481 mg/mL | Not Available | LogP | 4.6 | SANGSTER (1993) |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0159-0910000000-a12b321a54a44ae28972 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-014i-2910000000-d52410168e784872a5a6 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-06xx-9100000000-1ef5cd411f38c53a0a92 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0706-9100000000-e66a9147257053b93702 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0706-9100000000-2dd666a9a0355b1ca144 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-074i-9300000000-405ec308fe8c935c62a2 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-067i-0930000000-6a80d41e346f4b10104c | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-0910000000-a12b321a54a44ae28972 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014i-2910000000-d52410168e784872a5a6 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-1910000000-8246864bf316bce609a2 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9500000000-e05832f94ff0361363a2 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-05g0-9310000000-038e232cccb44582ec9c | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-2290000000-861c4b7b2da35b82ef7f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4l-9100000000-966cf4c6621fcec41368 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-054o-9000000000-d43dd32656ad22e95fdd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-06xx-9100000000-a71409efaf5fdd6ab0e1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positive | splash10-0706-9100000000-eb09296a8c4c7c381b38 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0002-0900000000-f22d8298d64e6f382279 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0002-0900000000-4bb88d3b1d2b7ac88152 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0002-0900000000-0c79a7257b53685108c6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0002-9600000000-25d268515337ef276c60 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-009b-9000000000-c00963f9b91f4a82e1ef | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0900000000-f22d8298d64e6f382279 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0900000000-4bb88d3b1d2b7ac88152 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0900000000-0c79a7257b53685108c6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0920000000-63cd88b9477cd281d342 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a5c-4910000000-94738a1f436dcf1abced | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9100000000-07ca8cffe5ba2f9f920d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0920000000-63cd88b9477cd281d342 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a5c-4910000000-94738a1f436dcf1abced | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9100000000-07ca8cffe5ba2f9f920d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-1655e63166b4d9dd4f59 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0532-1900000000-7c55a9ca2b49d4920029 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-ed8f6bcf96c68ac84738 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-1655e63166b4d9dd4f59 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0532-1900000000-7c55a9ca2b49d4920029 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-ed8f6bcf96c68ac84738 | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-074l-9100000000-911a01d38925d0de481f | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, CDCl3, experimental) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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Biospecimen Locations | - Blood
- Epidermis
- Liver
- Mammary Gland
- Milk
- Oocyte
- Prostate Tissue
- Thyroid Gland
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5.8 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9.8 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 9.4 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2446.11 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2496.03 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 599.0481 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1297.938 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 599.0481 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6689.37 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 10.2 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6290.01 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5740.88 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19.97 +/- 2.03 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21.06 +/- 2.77 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 8.13 +/- 0.19 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 3.33 +/- 0.74 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 17.42 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5990.475 +/- 1996.825 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 26.0586 +/- 0.42 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 48.5 +/- 23.4 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19.4 +/- 6.6 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6689.364 +/- 2146.587 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6190.158 +/- 1847.0632 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 33946.0597 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 41434.161 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 43430.988 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 53914.33 uM | Not Specified | Not Specified | Normal | | details | Oocyte | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Thyroid Gland | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000638 |
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DrugBank ID | DB03017 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB003010 |
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KNApSAcK ID | C00001221 |
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Chemspider ID | 3756 |
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KEGG Compound ID | C02679 |
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BioCyc ID | DODECANOATE |
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BiGG ID | 40351 |
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Wikipedia Link | Lauric_acid |
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METLIN ID | 5611 |
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PubChem Compound | 3893 |
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PDB ID | Not Available |
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ChEBI ID | 30805 |
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References |
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Synthesis Reference | Stepanova, G. A.; Markevich, V. S.; Garanin, V. I.; Stychinskii, G. F. Synthesis of lauric acid. Khimicheskaya Promyshlennost (Moscow, Russian Federation) (1974), (12), 930. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
- Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
- Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
- Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
- Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
- Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
- van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
- Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
- M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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