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 Date1.34835837E12 |
PubMed
Title | Date | PubMed |
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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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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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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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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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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 |
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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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Biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-3-hydroxyhexanoate) by metabolically engineered Escherichia coli strains. | 2001 Jul 5 |
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Agar-based magnetic affinity support for protein adsorption. | 2001 Jul-Aug |
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Detergents as probes of hydrophobic binding cavities in serum albumin and other water-soluble proteins. | 2001 Jun |
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Cold-induced changes in the energy coupling and the UCP3 level in rodent skeletal muscles. | 2001 Jun 1 |
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Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3. | 2001 Mar 1 |
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Changes in fatty acid composition during development of tissues of coconut (Cocos nucifera L.) embryos in the intact nut and in vitro. | 2001 May |
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Role of intrahelical arginine residues in functional properties of uncoupling protein (UCP1). | 2001 May 1 |
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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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2000 Research Laureate Medallion Award. | 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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pH-sensitive nanoparticles of poly(amino acid) dodecanoate complexes. | 2001 Nov 6 |
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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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Chemical characterization of lipid A from some marine proteobacteria. | 2001 Sep |
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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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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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Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length. | 2002 Apr |
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Antioxidant and cyclooxygenase activities of fatty acids found in food. | 2002 Apr 10 |
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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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The peroxisomal transporter gene ANT1 is regulated by a deviant oleate response element (ORE): characterization of the signal for fatty acid induction. | 2002 Jul 1 |
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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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Inhibitory effect of sulfur dioxide and other stress compounds in wine on the ATPase activity of Oenococcus oeni. | 2002 Jun 4 |
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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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Semisolid SLN dispersions for topical application: influence of formulation and production parameters on viscoelastic properties. | 2002 Mar |
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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 |
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The antimicrobial properties of milkfat after partial hydrolysis by calf pregastric lipase. | 2002 May 20 |
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
Wed Jul 05 23:59:50 UTC 2023
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on
Wed Jul 05 23:59:50 UTC 2023
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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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1356949
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143-07-7
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LAURIC ACID
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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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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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METABOLIC ENZYME -> SUBSTRATE | |||
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LIPID -> FATTY ACID |
Values are % of total.
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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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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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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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