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 822

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 8360	CLEAN ROUTINE Approved Use USE HELPS PROTECT AGAINST SUNBURN Launch Date 1.34835837E12

PubMed

Title	Date	PubMed


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
Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate.	2001	11358107
Cholesterol-lowering effect of NK-104, a 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitor, in guinea pig model of hyperlipidemia.	2001	11304935
In vivo absorption of medium-chain fatty acids by the rat colon exceeds that of short-chain fatty acids.	2001 Apr	11266379
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
Alkylsulfonates as probes of uncoupling protein transport mechanism. Ion pair transport demonstrates that direct H(+) translocation by UCP1 is not necessary for uncoupling.	2001 Aug 24	11468281
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
Biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-3-hydroxyhexanoate) by metabolically engineered Escherichia coli strains.	2001 Jul 5	11353413
Agar-based magnetic affinity support for protein adsorption.	2001 Jul-Aug	11485437
Detergents as probes of hydrophobic binding cavities in serum albumin and other water-soluble proteins.	2001 Jun	11371462
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
Role of intrahelical arginine residues in functional properties of uncoupling protein (UCP1).	2001 May 1	11318647
Cellular and lipopolysaccharide fatty acid composition of the type strains of Klebsiella pneumoniae, Klebsiella oxytoca, and Klebsiella nonpathogenic species.	2001 May-Jun	11785258
2000 Research Laureate Medallion Award.	2001 May-Jun	11322613
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
pH-sensitive nanoparticles of poly(amino acid) dodecanoate complexes.	2001 Nov 6	11672952
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
Chemical characterization of lipid A from some marine proteobacteria.	2001 Sep	11703190
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
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
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
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
Inhibitory effect of sulfur dioxide and other stress compounds in wine on the ATPase activity of Oenococcus oeni.	2002 Jun 4	12076806
Distribution of medium-chain FA in different lipid classes after administration of specific structured TAG in rats.	2002 Mar	11942486
Semisolid SLN dispersions for topical application: influence of formulation and production parameters on viscoelastic properties.	2002 Mar	11879997
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
The antimicrobial properties of milkfat after partial hydrolysis by calf pregastric lipase.	2002 May 20	12076524

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 `Wed Jul 05 23:59:50 UTC 2023` Edited by `admin` on `Wed Jul 05 23:59:50 UTC 2023`
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

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