AMMONIUM LAURATE

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

Structure Search

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

HIDE SMILES / InChI

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

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

Description
Sources: http://www.3dchem.com/Dodecanoic-acid.asp | https://www.ncbi.nlm.nih.gov/pubmed/19387482 | https://www.ewg.org/skindeep/ingredient/703428/LAURIC_ACID/#.Wmmmfa5l-po

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
other organism cell membrane 3 Target ID: GO:0044218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19665786	Modulator 817

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acne vulgaris 34 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19665786 https://www.ncbi.nlm.nih.gov/pubmed/19387482	Curative		Preclinical	Unknown Approved Use Unknown
SUNBURN 11 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f6db0332-58ed-4c82-a9dc-7fac621f1ac1	Inactive ingredient		Approved 8307	CLEAN ROUTINE Approved Use USE HELPS PROTECT AGAINST SUNBURN Launch Date 1.34835837E12

PubMed

Title	Date	PubMed
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.	1999 Jul 14	10403814
Comparative quantitative fatty acid analysis of triacylglycerols using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and gas chromatography.	2001	11675670
Structural and biological characterisation of a novel tetra-acyl lipid A from Escherichia coli F515 lipopolysaccharide acting as endotoxin antagonist in human monocytes.	2001	11521094
In vivo absorption of medium-chain fatty acids by the rat colon exceeds that of short-chain fatty acids.	2001 Apr	11266379
Isolation and preliminary characterization of the medium-chain fatty acid:CoA ligase responsible for activation of short- and medium-chain fatty acids in colonic mucosa from swine.	2001 Feb	11281196
Induction and inactivation of a cytochrome P450 confering herbicide resistance in wheat seedlings.	2001 Jan-Jun	11554440
Biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-3-hydroxyhexanoate) by metabolically engineered Escherichia coli strains.	2001 Jul 5	11353413
Antimicrobial effects of corn zein films impregnated with nisin, lauric acid, and EDTA.	2001 Jun	11403145
Cold-induced changes in the energy coupling and the UCP3 level in rodent skeletal muscles.	2001 Jun 1	11334791
Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3.	2001 Mar 1	11368173
Changes in fatty acid composition during development of tissues of coconut (Cocos nucifera L.) embryos in the intact nut and in vitro.	2001 May	11432910
Saturated fatty acids, but not unsaturated fatty acids, induce the expression of cyclooxygenase-2 mediated through Toll-like receptor 4.	2001 May 18	11278967
2000 Research Laureate Medallion Award.	2001 May-Jun	11322613
pH-sensitive nanoparticles of poly(amino acid) dodecanoate complexes.	2001 Nov 6	11672952
Enzyme activity of the cytochrome P-450 monooxygenase system in the presence of single chain lipid molecules.	2001 Nov-Dec	11837661
Production of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) by metabolically engineered Escherichia coli strains.	2001 Spring	11749180
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	12125016
Application of confocal laser scanning microscopy in characterization of chemical enhancers in drug-in-adhesive transdermal patches.	2002	12049487
Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length.	2002 Apr	11952815
Regio-specific hydroxylation of nonylphenol and the involvement of CYP2K- and CYP2M-like iso-enzymes in Atlantic salmon (Salmo salar).	2002 Feb	11792434
The hidden poetry of Solyman Brown, the "poet laureate of dentistry".	2002 Jul	12125699
Characterization of Type I and Type II myristoyl-CoA:protein N-myristoyltransferases with the Acyl-CoAs found on heterogeneously acylated retinal proteins.	2002 Jul	12123640
In-vitro release and transdermal fluxes of a highly lipophilic drug and of enhancers from matrix TDS.	2002 Jul 18	12106977
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	12093284
Full model for reversible kinetics of lipase-catalyzed sugar-ester synthesis in 2-methyl 2-butanol.	2002 Jun 30	12001171
Semisolid SLN dispersions for topical application: influence of formulation and production parameters on viscoelastic properties.	2002 Mar	11879997
Refractive index measurements in a reentrant isotropic-calamitic nematic phase transition.	2002 May	12059766

Patents

Sample Use Guides

In Vivo Use Guide

Mouse: Intradermal - 2 ug for 1 day; topical - 150 ug in Vaseline for 1 day.

Route of Administration: Other

In Vitro Use Guide

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 Dec 17 01:19:24 UTC 2022` Edited by `admin` on `Sat Dec 17 01:19:24 UTC 2022`
Record UNII	50IRX6VLIF
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AMMONIUM LAURATE

Systematic Name

English

DODECANOIC ACID, AMMONIUM SALT (1:1)

Common Name

English

LAURIC ACID, AMMONIUM SALT

Common Name

English

Code System Code Type Description

PUBCHEM

159661