Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H24O2 |
Molecular Weight | 200.3178 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCC(O)=O
InChI
InChIKey=POULHZVOKOAJMA-UHFFFAOYSA-N
InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)
Molecular Formula | C12H24O2 |
Molecular Weight | 200.3178 |
Charge | 0 |
Count |
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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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0044218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19665786 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Unknown Approved UseUnknown |
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Inactive ingredient | CLEAN ROUTINE Approved UseUSE HELPS PROTECT AGAINST SUNBURN Launch Date2012 |
PubMed
Title | Date | PubMed |
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Adrian P. Gee, PhD, Editor Laureate. | 2001 |
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Final report on the safety assessment of PEG-25 propylene glycol stearate, PEG-75 propylene glycol stearate, PEG-120 propylene glycol stearate, PEG-10 propylene glycol, PEG-8 propylene glycol cocoate, and PEG-55 propylene glycol oleate. | 2001 |
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Structural and biological characterisation of a novel tetra-acyl lipid A from Escherichia coli F515 lipopolysaccharide acting as endotoxin antagonist in human monocytes. | 2001 |
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Effect of fatty acids on arenavirus replication: inhibition of virus production by lauric acid. | 2001 |
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Identification and functional characterization of a new CYP2C9 variant (CYP2C9*5) expressed among African Americans. | 2001 Aug |
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Nanoparticles of a polyelectrolyte-fatty acid complex: carriers for Q10 and triiodothyronine. | 2001 Aug 10 |
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Palmitate decreases proton pumping of liver-type cytochrome c oxidase. | 2001 Dec |
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Induction and inactivation of a cytochrome P450 confering herbicide resistance in wheat seedlings. | 2001 Jan-Jun |
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Effects of tallow on the energy metabolism of wethers fed barley finishing diets. | 2001 Jul |
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Effects of dietary coconut oil on apolipoprotein B synthesis and VLDL secretion by calf liver slices. | 2001 Jul |
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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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A conservative amino acid substitution alters the regiospecificity of CYP94A2, a fatty acid hydroxylase from the plant Vicia sativa. | 2001 Jul 15 |
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Expression and induction of cytochrome P450s in rabbit parotid glands. | 2001 Jul 15 |
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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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Estimation of absorption enhancement by medium-chain fatty acids in rat large intestine. | 2001 Mar-Apr |
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A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, designed by prediction of the fluorescence intensity. | 2001 May 15 |
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Cellular and lipopolysaccharide fatty acid composition of the type strains of Klebsiella pneumoniae, Klebsiella oxytoca, and Klebsiella nonpathogenic species. | 2001 May-Jun |
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Cytochrome P450 4A11 expression in human keratinocytes: effects of ultraviolet irradiation. | 2001 Nov |
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Palmitate oxidation in rat hepatocytes is inhibited by foetal calf serum. | 2001 Nov |
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[Nobel Prize will be 100 years old. Emil von Behring: the first medicine laureate]. | 2001 Nov 1 |
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Enzyme activity of the cytochrome P-450 monooxygenase system in the presence of single chain lipid molecules. | 2001 Nov-Dec |
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Killing of Gram-positive cocci by fatty acids and monoglycerides. | 2001 Oct |
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Preparation and characterization of insulin-loaded acrylic hydrogels containing absorption enhancers. | 2001 Oct |
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Ethanol- and nicotine-induced membrane changes in embryonic and neonatal chick brains. | 2001 Oct |
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Combined effects of NaCl, NaOH, and biocides (monolaurin or lauric acid) on inactivation of Listeria monocytogenes and Pseudomonas spp. | 2001 Sep |
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Enzymatic modification of high-laurate canola to produce margarine fat. | 2001 Sep |
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A study of the expression of the xenobiotic-metabolising cytochrome P450 proteins and of testosterone metabolism in bovine liver. | 2001 Sep 1 |
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Production of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) by metabolically engineered Escherichia coli strains. | 2001 Spring |
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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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Autocatalytic mechanism and consequences of covalent heme attachment in the cytochrome P4504A family. | 2002 Apr 12 |
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Mutations in erg4 affect the sensitivity of Saccharomyces cerevisiae to medium-chain fatty acids. | 2002 Apr 15 |
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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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Regio-specific hydroxylation of nonylphenol and the involvement of CYP2K- and CYP2M-like iso-enzymes in Atlantic salmon (Salmo salar). | 2002 Feb |
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[Marius Tausk (1902-1990), influential endocrinologist and producer of medicines; a retrospect to mark the centenary of his birth]. | 2002 Feb 16 |
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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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The hidden poetry of Solyman Brown, the "poet laureate of dentistry". | 2002 Jul |
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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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Distribution of medium-chain FA in different lipid classes after administration of specific structured TAG in rats. | 2002 Mar |
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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 |
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Refractive index measurements in a reentrant isotropic-calamitic nematic phase transition. | 2002 May |
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Effect of lauric acid and nisin-impregnated soy-based films on the growth of Listeria monocytogenes on turkey bologna. | 2002 May |
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Enhanced electron transfer and lauric acid hydroxylation by site-directed mutagenesis of CYP119. | 2002 May 22 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19387482
Mouse: Intradermal - 2 ug for 1 day; topical - 150 ug in Vaseline for 1 day.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19387482
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
Mon Mar 31 18:31:43 GMT 2025
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Mon Mar 31 18:31:43 GMT 2025
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Record UNII |
1160N9NU9U
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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JECFA EVALUATION |
LAURIC ACID
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CFR |
21 CFR 172.860
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NCI_THESAURUS |
C68391
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DSLD |
1502 (Number of products:64)
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LOINC |
75099-2
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NCI_THESAURUS |
C68421
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EPA PESTICIDE CODE |
128918
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LOINC |
35150-2
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LOINC |
55873-4
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18262
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DTXSID5021590
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30805
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C68384
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1160N9NU9U
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1089
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1356949
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3893
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4642
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6814
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143-07-7
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LAURIC ACID
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1160N9NU9U
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100000172238
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1370594
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1363435
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m6709
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DB03017
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5026
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205-582-1
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C030358
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID | |||
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID |
Values are % of weight of fatty acid composition.
Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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SALT/SOLVATE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID |
JB Rossell and co-workers; JAOCS62(2), 221-230(1985).
Range weight is a mean.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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