Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:05:37 UTC |
---|
Update date | 2020-09-17 15:38:38 UTC |
---|
Primary ID | FDB003010 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | Dodecanoic acid |
---|
Description | Dodecanoic 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 Number | 143-07-7 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
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 | Docosanoic acid | manual | FEMA 2614 | db_source | N-dodecanoate | biospider | N-dodecanoic acid | biospider |
|
---|
Predicted Properties | |
---|
Chemical Formula | C12H24O2 |
---|
IUPAC name | dodecanoic acid |
---|
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 Key | POULHZVOKOAJMA-UHFFFAOYSA-N |
---|
Isomeric SMILES | CCCCCCCCCCCC(O)=O |
---|
Average Molecular Weight | 200.3178 |
---|
Monoisotopic Molecular Weight | 200.177630012 |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty acids and conjugates |
---|
Direct Parent | Medium-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 Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Biological role: Industrial application: |
---|
Physico-Chemical Properties |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Liquid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 71.95%; H 12.08%; O 15.97% | DFC |
---|
Melting Point | Mp 44° | DFC |
---|
Boiling Point | Bp0.65 141-142° (lit. gives a pressure range) | DFC |
---|
Experimental Water Solubility | 0.00481 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
---|
Experimental logP | 4.60 | SANGSTER (1993) |
---|
Experimental pKa | pKa 5.3 (20°) | DFC |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | d20 0.88 | DFC |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
EI-MS | Mass Spectrum (Electron Ionization) | splash10-074l-9100000000-911a01d38925d0de481f | 2014-09-20 | View Spectrum | GC-MS | Dodecanoic acid, non-derivatized, GC-MS Spectrum | splash10-0159-0910000000-a12b321a54a44ae28972 | Spectrum | GC-MS | Dodecanoic acid, 1 TMS, GC-MS Spectrum | splash10-014i-2910000000-d52410168e784872a5a6 | Spectrum | GC-MS | Dodecanoic acid, non-derivatized, GC-MS Spectrum | splash10-06xx-9100000000-1ef5cd411f38c53a0a92 | Spectrum | GC-MS | Dodecanoic acid, non-derivatized, GC-MS Spectrum | splash10-0706-9100000000-e66a9147257053b93702 | Spectrum | GC-MS | Dodecanoic acid, non-derivatized, GC-MS Spectrum | splash10-0706-9100000000-2dd666a9a0355b1ca144 | Spectrum | GC-MS | Dodecanoic acid, non-derivatized, GC-MS Spectrum | splash10-074i-9300000000-405ec308fe8c935c62a2 | Spectrum | GC-MS | Dodecanoic acid, non-derivatized, GC-MS Spectrum | splash10-067i-0930000000-6a80d41e346f4b10104c | Spectrum | GC-MS | Dodecanoic acid, non-derivatized, GC-MS Spectrum | splash10-0159-0910000000-a12b321a54a44ae28972 | Spectrum | GC-MS | Dodecanoic acid, non-derivatized, GC-MS Spectrum | splash10-014i-2910000000-d52410168e784872a5a6 | Spectrum | GC-MS | Dodecanoic acid, non-derivatized, GC-MS Spectrum | splash10-0159-1910000000-8246864bf316bce609a2 | Spectrum | Predicted GC-MS | Dodecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9500000000-e05832f94ff0361363a2 | Spectrum | Predicted GC-MS | Dodecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05g0-9310000000-038e232cccb44582ec9c | Spectrum | Predicted GC-MS | Dodecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Dodecanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-2290000000-861c4b7b2da35b82ef7f | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4l-9100000000-966cf4c6621fcec41368 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-054o-9000000000-d43dd32656ad22e95fdd | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-06xx-9100000000-a71409efaf5fdd6ab0e1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positive | splash10-0706-9100000000-eb09296a8c4c7c381b38 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0002-0900000000-f22d8298d64e6f382279 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0002-0900000000-4bb88d3b1d2b7ac88152 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0002-0900000000-0c79a7257b53685108c6 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0002-9600000000-25d268515337ef276c60 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-009b-9000000000-c00963f9b91f4a82e1ef | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0900000000-f22d8298d64e6f382279 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0900000000-4bb88d3b1d2b7ac88152 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-0900000000-0c79a7257b53685108c6 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0920000000-63cd88b9477cd281d342 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a5c-4910000000-94738a1f436dcf1abced | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9100000000-07ca8cffe5ba2f9f920d | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0920000000-63cd88b9477cd281d342 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a5c-4910000000-94738a1f436dcf1abced | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9100000000-07ca8cffe5ba2f9f920d | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-1655e63166b4d9dd4f59 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0532-1900000000-7c55a9ca2b49d4920029 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-ed8f6bcf96c68ac84738 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-1655e63166b4d9dd4f59 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0532-1900000000-7c55a9ca2b49d4920029 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-ed8f6bcf96c68ac84738 | 2015-05-27 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, CDCl3, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
|
---|
External Links |
---|
ChemSpider ID | 3756 |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | C02679 |
---|
Pubchem Compound ID | 3893 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | 30805 |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | DB03017 |
---|
HMDB ID | HMDB00638 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | CPX59-D:CPX59-D |
---|
EAFUS ID | 1984 |
---|
Dr. Duke ID | DODECANOIC-ACID|LAURIC-ACID |
---|
BIGG ID | 40351 |
---|
KNApSAcK ID | C00001221 |
---|
HET ID | DAO |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | 143-07-7 |
---|
GoodScent ID | rw1008181 |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Dodecanoic acid |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
---|
Anti bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti-viral | 22587 | An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19. | DUKE | Candidicide | | An agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases. | DUKE | Cyclooxygenase-1 inhibitor | 50630 | An agent that blocks the activity of cyclooxygenase-1 (COX-1), reducing inflammation and pain. Therapeutically, it is used to manage conditions like arthritis, and as a nonsteroidal anti-inflammatory drug (NSAID) to relieve pain, fever, and inflammation, while minimizing gastrointestinal side effects. | DUKE | Cyclooxygenase-2 inhibitor | 50629 | An agent that blocks the activity of cyclooxygenase-2 (COX-2), reducing inflammation and pain. Therapeutically, it is used to manage conditions such as arthritis, menstrual cramps, and other inflammatory disorders, providing relief from symptoms with reduced gastrointestinal side effects compared to non-selective NSAIDs. | DUKE | Name | 48318 | flavor | DUKE | Hypercholesterolemic | | A condition characterized by excessive cholesterol in the blood, playing a key role in cardiovascular disease. Therapeutically, hypercholesterolemic agents are used to lower cholesterol levels, with medical applications including the prevention and treatment of atherosclerosis, coronary artery disease, and stroke. | DUKE |
|
---|
Enzymes | Name | Gene Name | UniProt ID |
---|
Peroxisomal carnitine O-octanoyltransferase | CROT | Q9UKG9 | Carnitine O-palmitoyltransferase 2, mitochondrial | CPT2 | P23786 | Mitochondrial carnitine/acylcarnitine carrier protein | SLC25A20 | O43772 | S-acyl fatty acid synthase thioesterase, medium chain | OLAH | Q9NV23 | Ganglioside GM2 activator | GM2A | P17900 | Toll-like receptor 4 | TLR4 | O00206 |
|
---|
Pathways | Name | SMPDB Link | KEGG Link |
---|
Beta Oxidation of Very Long Chain Fatty Acids | SMP00052 | map01040 | Fatty Acid Biosynthesis | SMP00456 | Not Available | Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids | SMP00481 | Not Available |
|
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Flavor | Citations |
---|
metal |
- 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 |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fatty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| coconut |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bay oil |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
|
|
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not 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.
|
---|