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Details

Stereochemistry ACHIRAL
Molecular Formula C14H28O2
Molecular Weight 228.3709
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Myristic Acid

SMILES

CCCCCCCCCCCCCC(O)=O

InChI

InChIKey=TUNFSRHWOTWDNC-UHFFFAOYSA-N
InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)

HIDE SMILES / InChI
Molecular Formula C14H28O2
Molecular Weight 228.3709
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Sodium myristate is the sodium salt of myristic acid. It is used in the food as the binder, emulsifier and anticaking agent. It is one of the commonly occurring soaps. It is used in cosmetic as a cleansing and emulsifying agent.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Known to be CNS penetrant in rats. Human data not available.

Originator

Playfair, L.
3
Sources: DOI: 10.1080/14786444108650255

Approval Year

1995
203
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1447
Activator
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Not Provided
511
Unknown

Approved Use

Unknown
Diagnostic
Phase II
1147
Unknown

Approved Use

Unknown
Inactive ingredient
Approved
8583
Volu-Firm

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Differential use of myristoyl groups on neuronal calcium sensor proteins as a determinant of spatio-temporal aspects of Ca2+ signal transduction.
2002-04-19
Myristoylated alanine-rich C kinase substrate (MARCKS) sequesters spin-labeled phosphatidylinositol 4,5-bisphosphate in lipid bilayers.
2002-04-19
Enzyme activity of the cytochrome P-450 monooxygenase system in the presence of single chain lipid molecules.
2002-02-12
Enzymatic reaction of hydrogen peroxide-dependent peroxygenase cytochrome P450s: kinetic deuterium isotope effects and analyses by resonance Raman spectroscopy.
2002-02-12
Myristyl and palmityl acylation of pI 5.1 carboxylesterase from porcine intestine and liver.
2002-02
Differences in the fatty acid composition of larvae and metamorphosing sea lampreys, Petromyzon marinus.
2002-02
Oxidative stress induced cytokine production in isolated rat pancreatic acinar cells: effects of small-molecule antioxidants.
2002-02
Interaction of bovine (BSA) and human (HSA) serum albumins with ionic surfactants: spectroscopy and modelling.
2002-01-31
The linker domain of the Ha-Ras hypervariable region regulates interactions with exchange factors, Raf-1 and phosphoinositide 3-kinase.
2002-01-04
Permeation of a myristoylated dipeptide across the buccal mucosa: topological distribution and evaluation of tissue integrity.
2002-01-01
Serum free fatty acid pattern and risk of myocardial infarction: a case-control study.
2002-01
[Fatty acid-induced reversal of general anesthesia: chain length-dependence of antagonizing potencies of fatty acids].
2002-01
Intrastriatal injection of sonic hedgehog reduces behavioral impairment in a rat model of Parkinson's disease.
2002-01
Differences in calmodulin and calmodulin-binding proteins in phasic and tonic smooth muscles.
2002-01
Coexpression of proteins with methionine aminopeptidase and/or N-myristoyltransferase in Escherichia coli to increase acylation and homogeneity of protein preparations.
2002
Characterization of the binding of Photobacterium phosphoreum P-flavin by Vibrio harveyi Luciferase.
2001-12-15
Regulation of Golgi structure and function by ARF-like protein 1 (Arl1).
2001-12
Palmitate decreases proton pumping of liver-type cytochrome c oxidase.
2001-12
Inhibition and regulation of rat liver L-threonine dehydrogenase by different fatty acids and their derivatives.
2001-11-07
Fatty acid profiles of nitrite-oxidizing bacteria reflect their phylogenetic heterogeneity.
2001-11
Rational design of diflunisal analogues with reduced affinity for human serum albumin.
2001-10-31
The biology and enzymology of protein N-myristoylation.
2001-10-26
Phosphorylation of human N-myristoyltransferase by N-myristoylated SRC family tyrosine kinase members.
2001-10-19
Deletion of N-terminal myristoylation site of HIV Nef abrogates both MHC-1 and CD4 down-regulation.
2001-10-01
Site-directed mutagenesis of the putative distal helix of peroxygenase cytochrome P450.
2001-10-01
Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells.
2001-10
Effects of incubator humidity and hen age on yolk composition in broiler hatching eggs from young breeders.
2001-10
Ethanol- and nicotine-induced membrane changes in embryonic and neonatal chick brains.
2001-10
Differential effect of valproate and its Delta2- and Delta4-unsaturated metabolites, on the beta-oxidation rate of long-chain and medium-chain fatty acids.
2001-09-28
Optimization of carbohydrate fatty acid ester synthesis in organic media by a lipase from Candida antarctica.
2001-09-20
Palmitoylation of caveolin-1 at a single site (Cys-156) controls its coupling to the c-Src tyrosine kinase: targeting of dually acylated molecules (GPI-linked, transmembrane, or cytoplasmic) to caveolae effectively uncouples c-Src and caveolin-1 (TYR-14).
2001-09-14
Propranolol increases phosphatidic acid level via activation of phospholipase D.
2001-09
Rat pancreatic acinar cells express a cytosolic phospholipase D1b isoform that is not regulated by cholecystokinin.
2001-09
beta-Ketoacyl-[acyl carrier protein] synthase I of Escherichia coli: aspects of the condensation mechanism revealed by analyses of mutations in the active site pocket.
2001-08-21
Biosynthesis and structural characterization of medium-chain-length poly(3-hydroxyalkanoates) produced by Pseudomonas aeruginosa from fatty acids.
2001-08-20
Pre-steady-state kinetic studies of Saccharomyces cerevisiae myristoylCoA:protein N-myristoyltransferase mutants identify residues involved in catalysis.
2001-08-07
Fatty acid synthesis in African trypanosomes: a solution to the myristate mystery.
2001-08
A new double coupling system: synthesis of citronellyl acetate via transacetylation to citronellol from acetyl coenzyme A produced from glucose and free fatty acids.
2001-08
Role of AKT kinase in sphingosine-induced apoptosis in human hepatoma cells.
2001-08
Ca2+-myristoyl switch and membrane binding of chemically acylated neurocalcins.
2001-07-10
[Determination of higher fatty acids in human plasma].
2001-07
Molecular characterization of StCDPK1, a calcium-dependent protein kinase from Solanum tuberosum that is induced at the onset of tuber development.
2001-07
N-terminal fatty-acylation of sonic hedgehog enhances the induction of rodent ventral forebrain neurons.
2001-06
Expression, purification and characterization of cytochrome P450 Biol: a novel P450 involved in biotin synthesis in Bacillus subtilis.
2001-06
Differential mechanisms of glucose and palmitate in augmentation of insulin secretion in mouse pancreatic islets.
2001-06
Cox-2 inhibitory effects of naturally occurring and modified fatty acids.
2001-06
Acrylic resins as rate-controlling membranes in novel formulation of a nine-day 17beta-estradiol transdermal delivery system: in vitro and release modifier effect evaluation.
2001-05
Comparative quantitative fatty acid analysis of triacylglycerols using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and gas chromatography.
2001
Longitudinal study of fatty acids in plasma and erythrocyte phospholipids during pregnancy.
2001
Phorbol ester impairs electrical excitation of rat pancreatic beta-cells through PKC-independent activation of KATP channels.
2001
Patents

Patents

04150003
6
08137457
5
20050287473
3
20070149684
3
JP1054100A
5
JP1085660A
4
JP2000143550A
3
JP2000178208A
15
JP2000512663A
47
JP2000515909A
5
JP2001064692A
4
JP2001213763A
4
JP2001294538A
10
JP2001520656A
3
JP2002255788A
4
JP2002537070A
15
JP2002538219A
9
JP2004329194A
3
JP2005104766A
7
JP2005330317A
7
JP2005509588A
19
JP2006241010A
11
JP2009149599A
9
JP2009522777A
14
JP2010275564A
4
JP2010532434A
6
JP2011504934A
11
JP2011526928A
5
JP4111349B2
9
JPH00217156A
3
JPH00320212A
3
JPH00734091A
3
JPH01137939A
3
JPH01311192A
6
JPH0217156A
3
JPH02212598A
3
JPH02231701A
8
JPH0223856A
4
JPH03275633A
3
JPH03780A
3
JPH0399010A
3
JPH04112820A
3
JPH04169518A
3
JPH04316517A
3
JPH0517331A
3
JPH05194250A
6
JPH05311107A
3
JPH06345802A
21
JPH07267894A
3
JPH0782139A
3
JPH0782598A
3
JPH08151303A
3
JPH08173117A
3
JPH08295744A
5
JPH0840836A
3
JPH09110675A
20
JPH09143068A
3
JPH10183106A
3
JPH10330230A
3
JPH11139968A
5
JPH114671A
3
JPS06218620A
3
JPS06454100A
5
JPS0689817A
3
JPS53130602A
3
JPS55153714A
3
JPS5552346A
3
JPS58136669A
3
JPS62109885A
6
JPS63270533A
4
JPS6454100A
5

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Rous sarcoma virus-transformed cells were labeled for 2 h with either 1 mCi of [3H]palmitic acid or 0.2 mCi of [3H]myristic acid, and p60src was isolated by immunoprecipitation. The incorporation of [3H]myristic acid into p60src was ca. 100-fold greater than the incorporation of [3H]palmitic acid.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:36:33 GMT 2025
Edited
by admin
on Mon Mar 31 17:36:33 GMT 2025
Record UNII
0I3V7S25AW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FEMA NO. 2764
Preferred Name English
Myristic Acid
FCC   FHFI   HSDB   II   INCI   MART.   MI   USP-RS  
INCI  
Official Name English
MYRISTIC ACID [MI]
Common Name English
1-TRIDECANECARBOXYLIC ACID
Systematic Name English
NSC-5028
Code English
MYRISTATE
Common Name English
N-TETRADECAN-1-OIC ACID
Common Name English
MYRISTIC ACID [MART.]
Common Name English
MYRISTIC ACID [FCC]
Common Name English
TETRADECANOIC ACID
Systematic Name English
MYRISTIC ACID [FHFI]
Common Name English
MYRISTIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
MYRISTIC ACID [HSDB]
Common Name English
PRIFRAC-2942
Code English
MYRISTIC ACID [USP-RS]
Common Name English
PHILACID-1400
Code English
N-TETRADECANOIC ACID
Common Name English
MYRISTIC ACID [II]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68421
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
CFR 21 CFR 172.860
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
NCI_THESAURUS C68388
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
LOINC 75103-2
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
CFR 21 CFR 357.210
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
LOINC 35157-7
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
JECFA EVALUATION MYRISTIC ACID
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
LOINC 47783-6
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
DSLD 3280 (Number of products:15)
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
Code System Code Type Description
SMS_ID
100000154392
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
EVMPD
SUB128589
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
PUBCHEM
11005
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
MERCK INDEX
m7689
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY Merck Index
CAS
544-63-8
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
RXCUI
1356758
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID6021666
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PRIMARY
DRUG BANK
DB08231
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
RS_ITEM_NUM
1448990
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
CHEBI
30807
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
JECFA MONOGRAPH
1090
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
ChEMBL
CHEMBL111077
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
CHEBI
28875
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
DAILYMED
0I3V7S25AW
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
MESH
D019814
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
WIKIPEDIA
MYRISTIC ACID
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
NCI_THESAURUS
C68393
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
NSC
5028
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-875-2
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
FDA UNII
0I3V7S25AW
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
RXCUI
1313976
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
ALTERNATIVE
HSDB
5686
Created by admin on Mon Mar 31 17:36:33 GMT 2025 , Edited by admin on Mon Mar 31 17:36:33 GMT 2025
PRIMARY
Related Record Type Details
Structure of ALUMINUM MYRISTATE
SALT/SOLVATE -> PARENT
Structure of LITHIUM MYRISTATE
SALT/SOLVATE -> PARENT
Structure of ZINC MYRISTATE
SALT/SOLVATE -> PARENT
Structure of SODIUM MYRISTATE
SALT/SOLVATE -> PARENT
COTTONSEED OIL
LIPID -> FATTY ACID
G Jurriens and ACJ Kroesen, J Am Oil Chem Soc, 42(9)(1965)(average value). Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
Structure of DIETHANOLAMINE MYRISTATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM MYRISTATE
SALT/SOLVATE -> PARENT
Structure of TRIETHANOLAMINE MYRISTATE
SALT/SOLVATE -> PARENT
PALM OIL
LIPID -> FATTY ACID
Coconut oil
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
Structure of ALUMINUM DIMYRISTATE
SALT/SOLVATE -> PARENT
CANOLA OIL
LIPID -> FATTY ACID
RICE BRAN OIL
LIPID -> FATTY ACID
Structure of (2-Hydroxy-1,1-dimethylethyl)ammonium myristate
SALT/SOLVATE -> PARENT
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of MAGNESIUM MYRISTATE
SALT/SOLVATE -> PARENT
FISH OIL
LIPID -> FATTY ACID
MAY BE PRESENT
USP
Structure of MONOETHANOLAMINE MYRISTATE
SALT/SOLVATE -> PARENT
SOYBEAN OIL
LIPID -> FATTY ACID
Values are % of weight of fatty acid composition. O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range) Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of CALCIUM MYRISTATE
SALT/SOLVATE -> PARENT
Structure of MIRIPLATIN
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of Myristic Acid
ACTIVE MOIETY
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