LAURIC ACID

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

Structure Search

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)

HIDE SMILES / InChI

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

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 780

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acne vulgaris 30 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 8043	CLEAN ROUTINE Approved Use USE HELPS PROTECT AGAINST SUNBURN Launch Date 1.34835837E12

PubMed

Title	Date	PubMed
Adrian P. Gee, PhD, Editor Laureate.	2001	11953014
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	11800049
Fats and fatty acids as growth factors for Lactobacillus delbrueckii.	2001 Dec	11876356
Palmitate decreases proton pumping of liver-type cytochrome c oxidase.	2001 Dec	11737187
Cellular and lipopolysaccharide fatty acid composition of the type strains of Klebsiella pneumoniae, Klebsiella oxytoca, and Klebsiella nonpathogenic species.	2001 May-Jun	11785258
Cytochrome P450 4A11 expression in human keratinocytes: effects of ultraviolet irradiation.	2001 Nov	11736898
[Nobel Prize will be 100 years old. Emil von Behring: the first medicine laureate].	2001 Nov 1	11785467
Enzyme activity of the cytochrome P-450 monooxygenase system in the presence of single chain lipid molecules.	2001 Nov-Dec	11837661
Killing of Gram-positive cocci by fatty acids and monoglycerides.	2001 Oct	11890570
Amino acids protect epithelial cells from local toxicity by absorption enhancer, sodium laurate.	2001 Oct	11745705
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
Antioxidant and cyclooxygenase activities of fatty acids found in food.	2002 Apr 10	11929276
Autocatalytic mechanism and consequences of covalent heme attachment in the cytochrome P4504A family.	2002 Apr 12	11821421
Mutations in erg4 affect the sensitivity of Saccharomyces cerevisiae to medium-chain fatty acids.	2002 Apr 15	12020638
Cloning and expression of two novel pig liver and kidney fatty acid hydroxylases [cytochrome P450 (CYP)4A24 and CYP4A25].	2002 Apr 15	11931657
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	11830594
Effect of vehicles and penetration enhancers on the in vitro percutaneous absorption of tenoxicam through hairless mouse skin.	2002 Apr 2	11891070
Isolation and characterization of lipid in phloem sap of canola.	2002 Feb	11925046
Modulation of rat liver cytochrome P450 activity by prolonged red wine consumption.	2002 Feb	11879783
Regio-specific hydroxylation of nonylphenol and the involvement of CYP2K- and CYP2M-like iso-enzymes in Atlantic salmon (Salmo salar).	2002 Feb	11792434
Effects of cold exposure in vivo and uncouplers and recouplers in vitro on potato tuber mitochondria.	2002 Feb 15	11997132
[Marius Tausk (1902-1990), influential endocrinologist and producer of medicines; a retrospect to mark the centenary of his birth].	2002 Feb 16	11876039
Inhibition of bacterial foodborne pathogens by the lactoperoxidase system in combination with monolaurin.	2002 Feb 25	11883670
Fatty acid signalling in a mouse enteroendocrine cell line involves fatty acid aggregates rather than free fatty acids.	2002 Jan 1	11773321
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
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	12071844
In-vitro release and transdermal fluxes of a highly lipophilic drug and of enhancers from matrix TDS.	2002 Jul 18	12106977
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	12083870
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
Lauric acid is desaturated to 12:1n-3 by hepatocytes and rat liver homogenates.	2002 Jun	12120955
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	12001174
Full model for reversible kinetics of lipase-catalyzed sugar-ester synthesis in 2-methyl 2-butanol.	2002 Jun 30	12001171
Inhibitory effect of sulfur dioxide and other stress compounds in wine on the ATPase activity of Oenococcus oeni.	2002 Jun 4	12076806
Solyman Brown, a giant of dentistry and its poet laureate.	2002 Mar	12002252
Distribution of medium-chain FA in different lipid classes after administration of specific structured TAG in rats.	2002 Mar	11942486
Mechanisms of cytoprotective effect of amino acids on local toxicity caused by sodium laurate, a drug absorption enhancer, in intestinal epithelium.	2002 Mar	11920758
Semisolid SLN dispersions for topical application: influence of formulation and production parameters on viscoelastic properties.	2002 Mar	11879997
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	11846425
Variability in fatty acid and triacylglycerol composition of the oil of coconut (Cocos nucifera L.) hybrids and their parentals.	2002 Mar 13	11879040
Transdermal delivery of highly lipophilic drugs: in vitro fluxes of antiestrogens, permeation enhancers, and solvents from liquid formulations.	2002 May	12069170
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	12069166
Refractive index measurements in a reentrant isotropic-calamitic nematic phase transition.	2002 May	12059766
In vitro effects of fat, FA, and cholesterol on sphingomyelin hydrolysis induced by rat intestinal alkaline sphingomyelinase.	2002 May	12056588
Effect of lauric acid and nisin-impregnated soy-based films on the growth of Listeria monocytogenes on turkey bologna.	2002 May	12033424
The antimicrobial properties of milkfat after partial hydrolysis by calf pregastric lipase.	2002 May 20	12076524
Enhanced electron transfer and lauric acid hydroxylation by site-directed mutagenesis of CYP119.	2002 May 22	12010041

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 Jun 26 05:38:51 UTC 2021` Edited by `admin` on `Sat Jun 26 05:38:51 UTC 2021`
Record UNII	1160N9NU9U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAURIC ACID

Official Name

English

DODECANOIC ACID

Systematic Name

English

LAURIC ACID [INCI]

Common Name

English

LAURIC ACID [FHFI]

Common Name

English

LAURIC ACID [FCC]

Common Name

English

LAURIC ACID [WHO-DD]

Common Name

English

NSC-5026

Code

English

LAURIC ACID [MI]

Common Name

English

1-UNDECANECARBOXYLIC ACID

Systematic Name

English

N-DODECANOIC ACID

Common Name

English

DODECOIC ACID

Common Name

English

LAURIC ACID [USP-RS]

Common Name

English

LAUROSTEARIC ACID

Common Name

English

DODECANOIC ACID [HSDB]

Common Name

English

FEMA NO. 2614

Code

English

LAURIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

LAURIC ACID