Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H24O2 |
Molecular Weight | 200.3182 |
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 | 200.3182 |
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.
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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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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Fats and fatty acids as growth factors for Lactobacillus delbrueckii. | 2001 Dec |
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Estimation of absorption enhancement by medium-chain fatty acids in rat large intestine. | 2001 Mar-Apr |
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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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Killing of Gram-positive cocci by fatty acids and monoglycerides. | 2001 Oct |
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Amino acids protect epithelial cells from local toxicity by absorption enhancer, sodium laurate. | 2001 Oct |
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Chemical characterization of lipid A from some marine proteobacteria. | 2001 Sep |
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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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Application of confocal laser scanning microscopy in characterization of chemical enhancers in drug-in-adhesive transdermal patches. | 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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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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Cloning and expression of two novel pig liver and kidney fatty acid hydroxylases [cytochrome P450 (CYP)4A24 and CYP4A25]. | 2002 Apr 15 |
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An Escherichia coli mutant lacking the cold shock-induced palmitoleoyltransferase of lipid A biosynthesis: absence of unsaturated acyl chains and antibiotic hypersensitivity at 12 degrees C. | 2002 Apr 19 |
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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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Effects of cold exposure in vivo and uncouplers and recouplers in vitro on potato tuber mitochondria. | 2002 Feb 15 |
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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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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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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 |
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Full model for reversible kinetics of lipase-catalyzed sugar-ester synthesis in 2-methyl 2-butanol. | 2002 Jun 30 |
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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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Solyman Brown, a giant of dentistry and its poet laureate. | 2002 Mar |
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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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Transdermal delivery of highly lipophilic drugs: in vitro fluxes of antiestrogens, permeation enhancers, and solvents from liquid formulations. | 2002 May |
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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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Refractive index measurements in a reentrant isotropic-calamitic nematic phase transition. | 2002 May |
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In vitro effects of fat, FA, and cholesterol on sphingomyelin hydrolysis induced by rat intestinal alkaline sphingomyelinase. | 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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The antimicrobial properties of milkfat after partial hydrolysis by calf pregastric lipase. | 2002 May 20 |
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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
Sat Jun 26 05:38:51 UTC 2021
by
admin
on
Sat Jun 26 05:38:51 UTC 2021
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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
Created by
admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
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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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143-07-7
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C68384
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3893
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PRIMARY | |||
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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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1370594
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1363435
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PRIMARY | RxNorm | ||
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M6709
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DB03017
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205-582-1
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C030358
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1356949
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PRIMARY | USP-RS |
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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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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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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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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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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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LIPID -> FATTY ACID |
Values are % of total.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |