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

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 of LAURIC ACID

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

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
Fats and fatty acids as growth factors for Lactobacillus delbrueckii.
2001 Dec
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
Raman spectroscopy in magnetic fluids.
2001 Jan
Effects of vehicles and enhancers on transdermal delivery of melatonin.
2001 Jan 5
A conservative amino acid substitution alters the regiospecificity of CYP94A2, a fatty acid hydroxylase from the plant Vicia sativa.
2001 Jul 15
Biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-3-hydroxyhexanoate) by metabolically engineered Escherichia coli strains.
2001 Jul 5
Agar-based magnetic affinity support for protein adsorption.
2001 Jul-Aug
A transgenic mouse expressing human CYP4B1 in the liver.
2001 Jun 15
Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3.
2001 Mar 1
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
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
Inhibition and regulation of rat liver L-threonine dehydrogenase by different fatty acids and their derivatives.
2001 Nov 7
Industrial scale production of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate).
2001 Oct
Enzymatic modification of high-laurate canola to produce margarine fat.
2001 Sep
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
Application of confocal laser scanning microscopy in characterization of chemical enhancers in drug-in-adhesive transdermal patches.
2002
Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length.
2002 Apr
Antioxidant and cyclooxygenase activities of fatty acids found in food.
2002 Apr 10
Mutations in erg4 affect the sensitivity of Saccharomyces cerevisiae to medium-chain fatty acids.
2002 Apr 15
Cloning and expression of two novel pig liver and kidney fatty acid hydroxylases [cytochrome P450 (CYP)4A24 and CYP4A25].
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
Isolation and characterization of lipid in phloem sap of canola.
2002 Feb
Effects of cold exposure in vivo and uncouplers and recouplers in vitro on potato tuber mitochondria.
2002 Feb 15
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
In-vitro release and transdermal fluxes of a highly lipophilic drug and of enhancers from matrix TDS.
2002 Jul 18
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
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
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
Full model for reversible kinetics of lipase-catalyzed sugar-ester synthesis in 2-methyl 2-butanol.
2002 Jun 30
Inhibitory effect of sulfur dioxide and other stress compounds in wine on the ATPase activity of Oenococcus oeni.
2002 Jun 4
Distribution of medium-chain FA in different lipid classes after administration of specific structured TAG in rats.
2002 Mar
Transdermal delivery of highly lipophilic drugs: in vitro fluxes of antiestrogens, permeation enhancers, and solvents from liquid formulations.
2002 May
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
Refractive index measurements in a reentrant isotropic-calamitic nematic phase transition.
2002 May
In vitro effects of fat, FA, and cholesterol on sphingomyelin hydrolysis induced by rat intestinal alkaline sphingomyelinase.
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
Enhanced electron transfer and lauric acid hydroxylation by site-directed mutagenesis of CYP119.
2002 May 22
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 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
  • Download
Name Type Language
LAURIC ACID
FCC   FHFI   INCI   MI   USP-RS   WHO-DD  
INCI  
Official Name English
DODECANOIC ACID
HSDB  
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
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
CFR 21 CFR 172.860
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
NCI_THESAURUS C68391
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
DSLD 1502 (Number of products:64)
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
LOINC 75099-2
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
NCI_THESAURUS C68421
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
EPA PESTICIDE CODE 128918
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
LOINC 35150-2
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
LOINC 55873-4
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
Code System Code Type Description
EPA CompTox
143-07-7
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
NCI_THESAURUS
C68384
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
PUBCHEM
3893
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
DRUG CENTRAL
4642
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
HSDB
6814
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
CAS
143-07-7
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
WIKIPEDIA
LAURIC ACID
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
FDA UNII
1160N9NU9U
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
RXCUI
1370594
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
RXCUI
1363435
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M6709
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB03017
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-582-1
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
MESH
C030358
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY
USP_CATALOG
1356949
Created by admin on Sat Jun 26 05:38:52 UTC 2021 , Edited by admin on Sat Jun 26 05:38:52 UTC 2021
PRIMARY USP-RS
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of weight of fatty acid composition. Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY