LAURIC ACID

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

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	200.3178
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 846

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 8583	CLEAN ROUTINE Approved Use USE HELPS PROTECT AGAINST SUNBURN Launch Date 2012

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
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
Effect of fatty acids on arenavirus replication: inhibition of virus production by lauric acid.	2001	11402863
Identification and functional characterization of a new CYP2C9 variant (CYP2C9*5) expressed among African Americans.	2001 Aug	11455026
Nanoparticles of a polyelectrolyte-fatty acid complex: carriers for Q10 and triiodothyronine.	2001 Aug 10	11489312
Palmitate decreases proton pumping of liver-type cytochrome c oxidase.	2001 Dec	11737187
Induction and inactivation of a cytochrome P450 confering herbicide resistance in wheat seedlings.	2001 Jan-Jun	11554440
Effects of tallow on the energy metabolism of wethers fed barley finishing diets.	2001 Jul	11465378
Effects of dietary coconut oil on apolipoprotein B synthesis and VLDL secretion by calf liver slices.	2001 Jul	11432760
Fatty acid remodeling of glycosyl phosphatidylinositol anchors in Trypanosoma brucei: incorporation of fatty acids other than myristate.	2001 Jul	11420102
A conservative amino acid substitution alters the regiospecificity of CYP94A2, a fatty acid hydroxylase from the plant Vicia sativa.	2001 Jul 15	11437349
Expression and induction of cytochrome P450s in rabbit parotid glands.	2001 Jul 15	11389885
Antimicrobial effects of corn zein films impregnated with nisin, lauric acid, and EDTA.	2001 Jun	11403145
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	11396924
Estimation of absorption enhancement by medium-chain fatty acids in rat large intestine.	2001 Mar-Apr	11758652
A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, designed by prediction of the fluorescence intensity.	2001 May 15	11393836
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
Palmitate oxidation in rat hepatocytes is inhibited by foetal calf serum.	2001 Nov	11736689
[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
Preparation and characterization of insulin-loaded acrylic hydrogels containing absorption enhancers.	2001 Oct	11605651
Ethanol- and nicotine-induced membrane changes in embryonic and neonatal chick brains.	2001 Oct	11574286
Combined effects of NaCl, NaOH, and biocides (monolaurin or lauric acid) on inactivation of Listeria monocytogenes and Pseudomonas spp.	2001 Sep	11563526
Enzymatic modification of high-laurate canola to produce margarine fat.	2001 Sep	11559158
A study of the expression of the xenobiotic-metabolising cytochrome P450 proteins and of testosterone metabolism in bovine liver.	2001 Sep 1	11585060
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
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
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
[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
In-vitro release and transdermal fluxes of a highly lipophilic drug and of enhancers from matrix TDS.	2002 Jul 18	12106977
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
Variability in fatty acid and triacylglycerol composition of the oil of coconut (Cocos nucifera L.) hybrids and their parentals.	2002 Mar 13	11879040
Refractive index measurements in a reentrant isotropic-calamitic nematic phase transition.	2002 May	12059766
Effect of lauric acid and nisin-impregnated soy-based films on the growth of Listeria monocytogenes on turkey bologna.	2002 May	12033424
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 `Mon Mar 31 18:31:43 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:43 GMT 2025`
Record UNII	1160N9NU9U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DODECANOIC ACID

Preferred Name

English

LAURIC ACID

Official Name

English

LAURIC ACID [FHFI]

Common Name

English

LAURIC ACID [FCC]

Common Name

English

NSC-5026

Code

English

Lauric acid [WHO-DD]

Common Name

English

LAURIC ACID [MI]

Common Name

English

LAURATE

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