U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H23O2.Na
Molecular Weight 222.3
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM LAURATE

SMILES

CCCCCCCCCCCC(=O)[O-].[Na+]

InChI

InChIKey=BTURAGWYSMTVOW-UHFFFAOYSA-M
InChI=1S/C12H24O2.Na/c1-2-3-4-5-6-7-8-9-10-11-12(13)14;/h2-11H2,1H3,(H,13,14);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula C12H23O2
Molecular Weight 199.3103
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Inactive ingredient
CLEAN ROUTINE

Approved Use

USE HELPS PROTECT AGAINST SUNBURN

Launch Date

1.34835837E12
PubMed

PubMed

TitleDatePubMed
Adrian P. Gee, PhD, Editor Laureate.
2001
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
Comparative quantitative fatty acid analysis of triacylglycerols using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and gas chromatography.
2001
Structural and biological characterisation of a novel tetra-acyl lipid A from Escherichia coli F515 lipopolysaccharide acting as endotoxin antagonist in human monocytes.
2001
Effect of fatty acids on arenavirus replication: inhibition of virus production by lauric acid.
2001
Identification and functional characterization of a new CYP2C9 variant (CYP2C9*5) expressed among African Americans.
2001 Aug
Palmitate decreases proton pumping of liver-type cytochrome c oxidase.
2001 Dec
Fatty acid remodeling of glycosyl phosphatidylinositol anchors in Trypanosoma brucei: incorporation of fatty acids other than myristate.
2001 Jul
A conservative amino acid substitution alters the regiospecificity of CYP94A2, a fatty acid hydroxylase from the plant Vicia sativa.
2001 Jul 15
Expression and induction of cytochrome P450s in rabbit parotid glands.
2001 Jul 15
Antimicrobial effects of corn zein films impregnated with nisin, lauric acid, and EDTA.
2001 Jun
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
Estimation of absorption enhancement by medium-chain fatty acids in rat large intestine.
2001 Mar-Apr
Changes in fatty acid composition during development of tissues of coconut (Cocos nucifera L.) embryos in the intact nut and in vitro.
2001 May
A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, designed by prediction of the fluorescence intensity.
2001 May 15
Cellular and lipopolysaccharide fatty acid composition of the type strains of Klebsiella pneumoniae, Klebsiella oxytoca, and Klebsiella nonpathogenic species.
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
[Nobel Prize will be 100 years old. Emil von Behring: the first medicine laureate].
2001 Nov 1
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
Ethanol- and nicotine-induced membrane changes in embryonic and neonatal chick brains.
2001 Oct
Enzymatic modification of high-laurate canola to produce margarine fat.
2001 Sep
A study of the expression of the xenobiotic-metabolising cytochrome P450 proteins and of testosterone metabolism in bovine liver.
2001 Sep 1
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
Autocatalytic mechanism and consequences of covalent heme attachment in the cytochrome P4504A family.
2002 Apr 12
Mutations in erg4 affect the sensitivity of Saccharomyces cerevisiae to medium-chain fatty acids.
2002 Apr 15
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
Modulation of rat liver cytochrome P450 activity by prolonged red wine consumption.
2002 Feb
Regio-specific hydroxylation of nonylphenol and the involvement of CYP2K- and CYP2M-like iso-enzymes in Atlantic salmon (Salmo salar).
2002 Feb
Effects of cold exposure in vivo and uncouplers and recouplers in vitro on potato tuber mitochondria.
2002 Feb 15
Inhibition of bacterial foodborne pathogens by the lactoperoxidase system in combination with monolaurin.
2002 Feb 25
The hidden poetry of Solyman Brown, the "poet laureate of dentistry".
2002 Jul
Characterization of Type I and Type II myristoyl-CoA:protein N-myristoyltransferases with the Acyl-CoAs found on heterogeneously acylated retinal proteins.
2002 Jul
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
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
Lauric acid is desaturated to 12:1n-3 by hepatocytes and rat liver homogenates.
2002 Jun
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
Semisolid SLN dispersions for topical application: influence of formulation and production parameters on viscoelastic properties.
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
Variability in fatty acid and triacylglycerol composition of the oil of coconut (Cocos nucifera L.) hybrids and their parentals.
2002 Mar 13
Transdermal delivery of highly lipophilic drugs: in vitro fluxes of antiestrogens, permeation enhancers, and solvents from liquid formulations.
2002 May
Effect of lauric acid and nisin-impregnated soy-based films on the growth of Listeria monocytogenes on turkey bologna.
2002 May
The antimicrobial properties of milkfat after partial hydrolysis by calf pregastric lipase.
2002 May 20
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 Sat Jun 26 15:23:17 UTC 2021
Edited
by admin
on Sat Jun 26 15:23:17 UTC 2021
Record UNII
K146MR5EXO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM LAURATE
INCI  
INCI  
Official Name English
SODIUM LAURATE [INCI]
Common Name English
SODIUM DODECANOATE
Systematic Name English
DODECANOIC ACID, SODIUM SALT
Common Name English
SODIUM MONOLAURATE
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 79026
Created by admin on Sat Jun 26 15:23:17 UTC 2021 , Edited by admin on Sat Jun 26 15:23:17 UTC 2021
Code System Code Type Description
WIKIPEDIA
Sodium laurate
Created by admin on Sat Jun 26 15:23:17 UTC 2021 , Edited by admin on Sat Jun 26 15:23:17 UTC 2021
PRIMARY
CAS
629-25-4
Created by admin on Sat Jun 26 15:23:17 UTC 2021 , Edited by admin on Sat Jun 26 15:23:17 UTC 2021
PRIMARY
EPA CompTox
629-25-4
Created by admin on Sat Jun 26 15:23:17 UTC 2021 , Edited by admin on Sat Jun 26 15:23:17 UTC 2021
PRIMARY
PUBCHEM
2735067
Created by admin on Sat Jun 26 15:23:17 UTC 2021 , Edited by admin on Sat Jun 26 15:23:17 UTC 2021
PRIMARY
EVMPD
SUB62814
Created by admin on Sat Jun 26 15:23:17 UTC 2021 , Edited by admin on Sat Jun 26 15:23:17 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-082-4
Created by admin on Sat Jun 26 15:23:17 UTC 2021 , Edited by admin on Sat Jun 26 15:23:17 UTC 2021
PRIMARY
FDA UNII
K146MR5EXO
Created by admin on Sat Jun 26 15:23:17 UTC 2021 , Edited by admin on Sat Jun 26 15:23:17 UTC 2021
PRIMARY
RXCUI
1425357
Created by admin on Sat Jun 26 15:23:17 UTC 2021 , Edited by admin on Sat Jun 26 15:23:17 UTC 2021
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE