Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H23O2.H4N |
| Molecular Weight | 217.3483 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[NH4+].CCCCCCCCCCCC([O-])=O
InChI
InChIKey=VJCJAQSLASCYAW-UHFFFAOYSA-N
InChI=1S/C12H24O2.H3N/c1-2-3-4-5-6-7-8-9-10-11-12(13)14;/h2-11H2,1H3,(H,13,14);1H3
Lauric acid, or dodecanoic acid, is the main acid in coconut oil and in palm kernel oil, and is believed to have antimicrobial properties. The detected values of half maximal effective concentration (EC(50)) of lauric acid on P. acnes, S. aureus, and S. epidermidis growth indicate that P. acnes is the most sensitive to lauric acid among these bacteria. In addition, lauric acid did not induce cytotoxicity to human sebocytes. This data highlight the potential of using lauric acid as an alternative treatment for antibiotic therapy of acne vulgaris. Lauric acid is used in the manufacture of soaps, detergents, cosmetics, and lauryl alcohol.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate. | 2001 |
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| Cholesterol-lowering effect of NK-104, a 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitor, in guinea pig model of hyperlipidemia. | 2001 |
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| Oxidative stress, microsomal and peroxisomal fatty acid oxidation in the liver of rats treated with acetone. | 2001 Apr |
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| In vivo absorption of medium-chain fatty acids by the rat colon exceeds that of short-chain fatty acids. | 2001 Apr |
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| The kinetic and spectral characterization of the E. coli-expressed mammalian CYP4A7: cytochrome b5 effects vary with substrate. | 2001 Jan 15 |
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| Fatty acid remodeling of glycosyl phosphatidylinositol anchors in Trypanosoma brucei: incorporation of fatty acids other than myristate. | 2001 Jul |
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| Antimicrobial effects of corn zein films impregnated with nisin, lauric acid, and EDTA. | 2001 Jun |
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| Reconstitution of the enzymatic activities of cytochrome P450s using recombinant flavocytochromes containing rat cytochrome b(5) fused to NADPH--cytochrome P450 reductase with various membrane-binding segments. | 2001 Jun 15 |
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| Palmitate oxidation in rat hepatocytes is inhibited by foetal calf serum. | 2001 Nov |
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| Inhibition and regulation of rat liver L-threonine dehydrogenase by different fatty acids and their derivatives. | 2001 Nov 7 |
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| Killing of Gram-positive cocci by fatty acids and monoglycerides. | 2001 Oct |
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| Chemical characterization of lipid A from some marine proteobacteria. | 2001 Sep |
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| Identification of omega hydroxy fatty acids in biological samples as their pentafluoropropyl derivatives by gas chromatography/mass spectrometry with positive and negative ion detection. | 2002 |
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| Antioxidant and cyclooxygenase activities of fatty acids found in food. | 2002 Apr 10 |
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| Effect of vehicles and penetration enhancers on the in vitro percutaneous absorption of tenoxicam through hairless mouse skin. | 2002 Apr 2 |
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| Isolation and characterization of lipid in phloem sap of canola. | 2002 Feb |
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| Modulation of rat liver cytochrome P450 activity by prolonged red wine consumption. | 2002 Feb |
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| Inhibition of bacterial foodborne pathogens by the lactoperoxidase system in combination with monolaurin. | 2002 Feb 25 |
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| Fatty acid signalling in a mouse enteroendocrine cell line involves fatty acid aggregates rather than free fatty acids. | 2002 Jan 1 |
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| Characterization of Type I and Type II myristoyl-CoA:protein N-myristoyltransferases with the Acyl-CoAs found on heterogeneously acylated retinal proteins. | 2002 Jul |
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| In-vitro release and transdermal fluxes of a highly lipophilic drug and of enhancers from matrix TDS. | 2002 Jul 18 |
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| Suppressive effect of saturated acyl L-ascorbate on the oxidation of linoleic acid encapsulated with maltodextrin or gum arabic by spray-drying. | 2002 Jul 3 |
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| The biosynthetic incorporation of short-chain linear saturated fatty acids by Acholeplasma laidlawii B may suppress cell growth by perturbing membrane lipid polar headgroup distribution. | 2002 Jul 9 |
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| Lauric acid is desaturated to 12:1n-3 by hepatocytes and rat liver homogenates. | 2002 Jun |
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| Mechanisms of cytoprotective effect of amino acids on local toxicity caused by sodium laurate, a drug absorption enhancer, in intestinal epithelium. | 2002 Mar |
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| Semisolid SLN dispersions for topical application: influence of formulation and production parameters on viscoelastic properties. | 2002 Mar |
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| Variability in fatty acid and triacylglycerol composition of the oil of coconut (Cocos nucifera L.) hybrids and their parentals. | 2002 Mar 13 |
Patents
Sample Use Guides
Mouse: Intradermal - 2 ug for 1 day; topical - 150 ug in Vaseline for 1 day.
Route of Administration:
Other
To compare dose-response effects of lauric acid on the growth of bacteria that are present in the skin flora, P. acnes, Staphylococcus aureus (S. aureus), and Staphylococcus epidermidis (S. epidermidis) were co-cultured with agent at various concentrations for 72, 24, and 48 hours. The half maximal effective concentration of lauric acid on P. acnes growth was the lowest among the bacteria tested, suggesting that P. acnes is more sensitive than S. aureus and S. epidermidis. The values of MIC (1.95 ug/ml) and the half maximal effective concentration (1.5 ug/ml) of lauric acid were also determined using a different strain of P. acnes (ATCC 11827).
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159661
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219-439-6
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2437-23-2
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50IRX6VLIF
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C030358
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1442516
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DTXSID6027476
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
