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

Details

Stereochemistry ACHIRAL
Molecular Formula C12H24O2
Molecular Weight 200.3178
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

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
Structural and biological characterisation of a novel tetra-acyl lipid A from Escherichia coli F515 lipopolysaccharide acting as endotoxin antagonist in human monocytes.
2001
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
Cholesterol-lowering effect of NK-104, a 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitor, in guinea pig model of hyperlipidemia.
2001
In vivo absorption of medium-chain fatty acids by the rat colon exceeds that of short-chain fatty acids.
2001 Apr
Identification and functional characterization of a new CYP2C9 variant (CYP2C9*5) expressed among African Americans.
2001 Aug
Nanoparticles of a polyelectrolyte-fatty acid complex: carriers for Q10 and triiodothyronine.
2001 Aug 10
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
Induction and inactivation of a cytochrome P450 confering herbicide resistance in wheat seedlings.
2001 Jan-Jun
Effects of tallow on the energy metabolism of wethers fed barley finishing diets.
2001 Jul
Effects of dietary coconut oil on apolipoprotein B synthesis and VLDL secretion by calf liver slices.
2001 Jul
Fatty acid remodeling of glycosyl phosphatidylinositol anchors in Trypanosoma brucei: incorporation of fatty acids other than myristate.
2001 Jul
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
Detergents as probes of hydrophobic binding cavities in serum albumin and other water-soluble proteins.
2001 Jun
Cold-induced changes in the energy coupling and the UCP3 level in rodent skeletal muscles.
2001 Jun 1
Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3.
2001 Mar 1
Changes in fatty acid composition during development of tissues of coconut (Cocos nucifera L.) embryos in the intact nut and in vitro.
2001 May
Role of intrahelical arginine residues in functional properties of uncoupling protein (UCP1).
2001 May 1
Cellular and lipopolysaccharide fatty acid composition of the type strains of Klebsiella pneumoniae, Klebsiella oxytoca, and Klebsiella nonpathogenic species.
2001 May-Jun
2000 Research Laureate Medallion Award.
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
[Nobel Prize will be 100 years old. Emil von Behring: the first medicine laureate].
2001 Nov 1
pH-sensitive nanoparticles of poly(amino acid) dodecanoate complexes.
2001 Nov 6
Preparation and characterization of insulin-loaded acrylic hydrogels containing absorption enhancers.
2001 Oct
Ethanol- and nicotine-induced membrane changes in embryonic and neonatal chick brains.
2001 Oct
Chemical characterization of lipid A from some marine proteobacteria.
2001 Sep
Combined effects of NaCl, NaOH, and biocides (monolaurin or lauric acid) on inactivation of Listeria monocytogenes and Pseudomonas spp.
2001 Sep
Enzymatic modification of high-laurate canola to produce margarine fat.
2001 Sep
A study of the expression of the xenobiotic-metabolising cytochrome P450 proteins and of testosterone metabolism in bovine liver.
2001 Sep 1
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
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
Fatty acid signalling in a mouse enteroendocrine cell line involves fatty acid aggregates rather than free fatty acids.
2002 Jan 1
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
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
Semisolid SLN dispersions for topical application: influence of formulation and production parameters on viscoelastic properties.
2002 Mar
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
The antimicrobial properties of milkfat after partial hydrolysis by calf pregastric lipase.
2002 May 20
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 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
  • 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 Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
CFR 21 CFR 172.860
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
NCI_THESAURUS C68391
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
DSLD 1502 (Number of products:64)
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
LOINC 75099-2
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
NCI_THESAURUS C68421
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
EPA PESTICIDE CODE 128918
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
LOINC 35150-2
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
LOINC 55873-4
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
Code System Code Type Description
CHEBI
18262
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID5021590
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
CHEBI
30805
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
NCI_THESAURUS
C68384
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
DAILYMED
1160N9NU9U
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
RS_ITEM_NUM
1356949
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
PUBCHEM
3893
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
DRUG CENTRAL
4642
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
HSDB
6814
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
CAS
143-07-7
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
WIKIPEDIA
LAURIC ACID
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
FDA UNII
1160N9NU9U
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
SMS_ID
100000172238
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
RXCUI
1370594
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
ALTERNATIVE
RXCUI
1363435
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M6709
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB03017
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
NSC
5026
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-582-1
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
MESH
C030358
Created by admin on Wed Jul 05 23:59:50 UTC 2023 , Edited by admin on Wed Jul 05 23:59:50 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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SALT/SOLVATE -> PARENT
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LIPID -> FATTY ACID
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SALT/SOLVATE -> PARENT
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY