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
| Molecular Formula | C12H24O2 |
| Molecular Weight | 200.3178 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H3N |
| Molecular Weight | 17.0305 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Adrian P. Gee, PhD, Editor Laureate. | 2001 |
|
| Comparative quantitative fatty acid analysis of triacylglycerols using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and gas chromatography. | 2001 |
|
| Effect of fatty acids on arenavirus replication: inhibition of virus production by lauric acid. | 2001 |
|
| Cholesterol-lowering effect of NK-104, a 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitor, in guinea pig model of hyperlipidemia. | 2001 |
|
| Alkylsulfonates as probes of uncoupling protein transport mechanism. Ion pair transport demonstrates that direct H(+) translocation by UCP1 is not necessary for uncoupling. | 2001 Aug 24 |
|
| Palmitate decreases proton pumping of liver-type cytochrome c oxidase. | 2001 Dec |
|
| Raman spectroscopy in magnetic fluids. | 2001 Jan |
|
| Characterization of a new member of the fatty acid-binding protein family that binds all-trans-retinol. | 2001 Jan 12 |
|
| The kinetic and spectral characterization of the E. coli-expressed mammalian CYP4A7: cytochrome b5 effects vary with substrate. | 2001 Jan 15 |
|
| Effects of vehicles and enhancers on transdermal delivery of melatonin. | 2001 Jan 5 |
|
| Effects of tallow on the energy metabolism of wethers fed barley finishing diets. | 2001 Jul |
|
| Expression and induction of cytochrome P450s in rabbit parotid glands. | 2001 Jul 15 |
|
| Agar-based magnetic affinity support for protein adsorption. | 2001 Jul-Aug |
|
| A transgenic mouse expressing human CYP4B1 in the liver. | 2001 Jun 15 |
|
| 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 |
|
| Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3. | 2001 Mar 1 |
|
| Estimation of absorption enhancement by medium-chain fatty acids in rat large intestine. | 2001 Mar-Apr |
|
| A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, designed by prediction of the fluorescence intensity. | 2001 May 15 |
|
| Saturated fatty acids, but not unsaturated fatty acids, induce the expression of cyclooxygenase-2 mediated through Toll-like receptor 4. | 2001 May 18 |
|
| Cellular and lipopolysaccharide fatty acid composition of the type strains of Klebsiella pneumoniae, Klebsiella oxytoca, and Klebsiella nonpathogenic species. | 2001 May-Jun |
|
| 2000 Research Laureate Medallion Award. | 2001 May-Jun |
|
| Cytochrome P450 4A11 expression in human keratinocytes: effects of ultraviolet irradiation. | 2001 Nov |
|
| Palmitate oxidation in rat hepatocytes is inhibited by foetal calf serum. | 2001 Nov |
|
| Phenylalanine 393 exerts thermodynamic control over the heme of flavocytochrome P450 BM3. | 2001 Nov 13 |
|
| Inhibition and regulation of rat liver L-threonine dehydrogenase by different fatty acids and their derivatives. | 2001 Nov 7 |
|
| Enzyme activity of the cytochrome P-450 monooxygenase system in the presence of single chain lipid molecules. | 2001 Nov-Dec |
|
| Killing of Gram-positive cocci by fatty acids and monoglycerides. | 2001 Oct |
|
| Amino acids protect epithelial cells from local toxicity by absorption enhancer, sodium laurate. | 2001 Oct |
|
| Industrial scale production of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate). | 2001 Oct |
|
| The Neisseria gonorrhoeae lpxLII gene encodes for a late-functioning lauroyl acyl transferase, and a null mutation within the gene has a significant effect on the induction of acute inflammatory responses. | 2001 Oct |
|
| Chemical characterization of lipid A from some marine proteobacteria. | 2001 Sep |
|
| Production of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) by metabolically engineered Escherichia coli strains. | 2001 Spring |
|
| 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 |
|
| Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length. | 2002 Apr |
|
| Cloning and expression of two novel pig liver and kidney fatty acid hydroxylases [cytochrome P450 (CYP)4A24 and CYP4A25]. | 2002 Apr 15 |
|
| Effect of vehicles and penetration enhancers on the in vitro percutaneous absorption of tenoxicam through hairless mouse skin. | 2002 Apr 2 |
|
| Isolation and characterization of lipid in phloem sap of canola. | 2002 Feb |
|
| [Marius Tausk (1902-1990), influential endocrinologist and producer of medicines; a retrospect to mark the centenary of his birth]. | 2002 Feb 16 |
|
| Fatty acid signalling in a mouse enteroendocrine cell line involves fatty acid aggregates rather than free fatty acids. | 2002 Jan 1 |
|
| In-vitro release and transdermal fluxes of a highly lipophilic drug and of enhancers from matrix TDS. | 2002 Jul 18 |
|
| Influence of glucose solubility and dissolution rate on the kinetics of lipase catalyzed synthesis of glucose laurate in 2-methyl 2-butanol. | 2002 Jun 30 |
|
| Full model for reversible kinetics of lipase-catalyzed sugar-ester synthesis in 2-methyl 2-butanol. | 2002 Jun 30 |
|
| Solyman Brown, a giant of dentistry and its poet laureate. | 2002 Mar |
|
| Mechanisms of cytoprotective effect of amino acids on local toxicity caused by sodium laurate, a drug absorption enhancer, in intestinal epithelium. | 2002 Mar |
|
| Quantification of lipopolysaccharides in outer membrane vesicle vaccines against meningococcal disease. High-performance liquid chromatographic determination of the constituent 3-hydroxy-lauric acid. | 2002 Mar |
|
| Analysis methods of polysorbate 20: A new method to assess the stability of polysorbate 20 and established methods that may overlook degraded polysorbate 20. | 2002 May |
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).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:50:52 GMT 2023
by
admin
on
Fri Dec 15 18:50:52 GMT 2023
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| Record UNII |
50IRX6VLIF
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID6027476
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PARENT -> SALT/SOLVATE |
