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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 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 200.3178
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

1982
94
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
817
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Preclinical
Unknown

Approved Use

Unknown
Inactive ingredient
Approved
8307
CLEAN ROUTINE

Approved Use

USE HELPS PROTECT AGAINST SUNBURN

Launch Date

1.34835837E12
PubMed

PubMed

TitleDatePubMed
Adrian P. Gee, PhD, Editor Laureate.
2001
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
Fats and fatty acids as growth factors for Lactobacillus delbrueckii.
2001 Dec
Palmitate decreases proton pumping of liver-type cytochrome c oxidase.
2001 Dec
Cellular and lipopolysaccharide fatty acid composition of the type strains of Klebsiella pneumoniae, Klebsiella oxytoca, and Klebsiella nonpathogenic species.
2001 May-Jun
Palmitate oxidation in rat hepatocytes is inhibited by foetal calf serum.
2001 Nov
[Nobel Prize will be 100 years old. Emil von Behring: the first medicine laureate].
2001 Nov 1
Phenylalanine 393 exerts thermodynamic control over the heme of flavocytochrome P450 BM3.
2001 Nov 13
Inhibition and regulation of rat liver L-threonine dehydrogenase by different fatty acids and their derivatives.
2001 Nov 7
Enzyme activity of the cytochrome P-450 monooxygenase system in the presence of single chain lipid molecules.
2001 Nov-Dec
Killing of Gram-positive cocci by fatty acids and monoglycerides.
2001 Oct
Amino acids protect epithelial cells from local toxicity by absorption enhancer, sodium laurate.
2001 Oct
Industrial scale production of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate).
2001 Oct
Chemical characterization of lipid A from some marine proteobacteria.
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
Autocatalytic mechanism and consequences of covalent heme attachment in the cytochrome P4504A family.
2002 Apr 12
Mutations in erg4 affect the sensitivity of Saccharomyces cerevisiae to medium-chain fatty acids.
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
Modulation of rat liver cytochrome P450 activity by prolonged red wine consumption.
2002 Feb
Regio-specific hydroxylation of nonylphenol and the involvement of CYP2K- and CYP2M-like iso-enzymes in Atlantic salmon (Salmo salar).
2002 Feb
Effects of cold exposure in vivo and uncouplers and recouplers in vitro on potato tuber mitochondria.
2002 Feb 15
[Marius Tausk (1902-1990), influential endocrinologist and producer of medicines; a retrospect to mark the centenary of his birth].
2002 Feb 16
Inhibition of bacterial foodborne pathogens by the lactoperoxidase system in combination with monolaurin.
2002 Feb 25
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
Solyman Brown, a giant of dentistry and its poet laureate.
2002 Mar
Distribution of medium-chain FA in different lipid classes after administration of specific structured TAG in rats.
2002 Mar
Mechanisms of cytoprotective effect of amino acids on local toxicity caused by sodium laurate, a drug absorption enhancer, in intestinal epithelium.
2002 Mar
Semisolid SLN dispersions for topical application: influence of formulation and production parameters on viscoelastic properties.
2002 Mar
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
Variability in fatty acid and triacylglycerol composition of the oil of coconut (Cocos nucifera L.) hybrids and their parentals.
2002 Mar 13
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

Patents

04471098
3
04541839
3
04554327
3
05891921
5
07872095
5
JP1029496A
3
JP1040417A
3
JP1070415A
3
JP2000109787A
3
JP2000157228A
3
JP2000178208A
15
JP2000247861A
4
JP2000270769A
3
JP2000313894A
3
JP2001017137A
3
JP2001081024A
3
JP2001123149A
3
JP2002129057A
3
JP2002537321A
7
JP2003213299A
3
JP2003524586A
7
JP2004531464A
13
JP2006232860A
8
JP2006523845A
4
JP2007105705A
3
JP2007169248A
3
JP2008182961A
3
JP2008506782A
3
JP2009178072A
3
JP2010038796A
7
JP2010065231A
4
JP2010148385A
3
JP2010228976A
3
JP2011115075A
3
JP2011168716A
3
JP2011506492A
5
JP2011513532A
6
JP2011524337A
20
JP2011525128A
3
JP2013539984A
3
JP2858839B2
5
JP3621425B2
10
JP4680382B2
8
JP4812169B2
18
JP4838936B2
15
JP4850390B2
17
JPH00753369A
3
JPH00860196A
3
JPH00987671A
3
JPH01138299A
4
JPH02120372A
3
JPH02135213A
3
JPH02222698A
3
JPH02231037A
3
JPH02242874A
5
JPH0260591A
3
JPH03126758A
3
JPH0317149A
3
JPH04131082A
3
JPH04178474A
3
JPH05156287A
3
JPH06345802A
21
JPH0688100A
3
JPS59230141A
3
JPS595142A
4
JPS6079088A
4
US2572238
3

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 Fri Dec 16 20:31:48 UTC 2022
Edited
by admin
on Fri Dec 16 20:31:48 UTC 2022
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
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
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
CFR 21 CFR 172.860
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
NCI_THESAURUS C68391
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
DSLD 1502 (Number of products:64)
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
LOINC 75099-2
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
NCI_THESAURUS C68421
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
EPA PESTICIDE CODE 128918
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
LOINC 35150-2
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
LOINC 55873-4
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
Code System Code Type Description
CHEBI
18262
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
EPA CompTox
DTXSID5021590
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
CHEBI
30805
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
NCI_THESAURUS
C68384
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
DAILYMED
1160N9NU9U
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
RS_ITEM_NUM
1356949
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
PUBCHEM
3893
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
DRUG CENTRAL
4642
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
HSDB
6814
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
CAS
143-07-7
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
WIKIPEDIA
LAURIC ACID
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
FDA UNII
1160N9NU9U
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
RXCUI
1370594
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
ALTERNATIVE
RXCUI
1363435
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY RxNorm
MERCK INDEX
M6709
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY Merck Index
DRUG BANK
DB03017
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
NSC
5026
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
ECHA (EC/EINECS)
205-582-1
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
MESH
C030358
Created by admin on Fri Dec 16 20:31:48 UTC 2022 , Edited by admin on Fri Dec 16 20:31:48 UTC 2022
PRIMARY
Related Record Type Details
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of ZINC LAURATE
SALT/SOLVATE -> PARENT
PALM OIL
LIPID -> FATTY ACID
Values are % of total.
Structure of SODIUM TAURINE LAURATE
SALT/SOLVATE -> PARENT
SOYBEAN OIL
LIPID -> FATTY ACID
Values are % of weight of fatty acid composition. Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
Structure of MORPHOLINE LAURATE
SALT/SOLVATE -> PARENT
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
IRIS VERSICOLOR ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Coconut oil
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
Structure of MAGNESIUM LAURATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM LAURATE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2E1
METABOLIC ENZYME -> SUBSTRATE
Structure of SODIUM LAURATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM TAURINE LAURATE
SALT/SOLVATE -> PARENT
Structure of AMMONIUM LAURATE
SALT/SOLVATE -> PARENT
Structure of CALCIUM LAURATE
SALT/SOLVATE -> PARENT
Structure of TRIETHANOLAMINE LAURATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of LAURIC ACID
ACTIVE MOIETY
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