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

Details

Stereochemistry ACHIRAL
Molecular Formula C14H28O2
Molecular Weight 228.3715
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 228.3715
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

CNS Activity

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

Originator

Sources: DOI: 10.1080/14786444108650255

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Inactive ingredient
Volu-Firm

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Fatty acid synthesis in African trypanosomes: a solution to the myristate mystery.
2001 Aug
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 Aug
Role of AKT kinase in sphingosine-induced apoptosis in human hepatoma cells.
2001 Aug
Biosynthesis and structural characterization of medium-chain-length poly(3-hydroxyalkanoates) produced by Pseudomonas aeruginosa from fatty acids.
2001 Aug 20
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 Aug 21
Pre-steady-state kinetic studies of Saccharomyces cerevisiae myristoylCoA:protein N-myristoyltransferase mutants identify residues involved in catalysis.
2001 Aug 7
Regulation of Golgi structure and function by ARF-like protein 1 (Arl1).
2001 Dec
Palmitate decreases proton pumping of liver-type cytochrome c oxidase.
2001 Dec
Characterization of the binding of Photobacterium phosphoreum P-flavin by Vibrio harveyi Luciferase.
2001 Dec 15
[Determination of higher fatty acids in human plasma].
2001 Jul
Molecular characterization of StCDPK1, a calcium-dependent protein kinase from Solanum tuberosum that is induced at the onset of tuber development.
2001 Jul
Fatty acid remodeling of glycosyl phosphatidylinositol anchors in Trypanosoma brucei: incorporation of fatty acids other than myristate.
2001 Jul
Ca2+-myristoyl switch and membrane binding of chemically acylated neurocalcins.
2001 Jul 10
N-terminal fatty-acylation of sonic hedgehog enhances the induction of rodent ventral forebrain neurons.
2001 Jun
Expression, purification and characterization of cytochrome P450 Biol: a novel P450 involved in biotin synthesis in Bacillus subtilis.
2001 Jun
Differential mechanisms of glucose and palmitate in augmentation of insulin secretion in mouse pancreatic islets.
2001 Jun
Cox-2 inhibitory effects of naturally occurring and modified fatty acids.
2001 Jun
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 May
Fatty acid profiles of nitrite-oxidizing bacteria reflect their phylogenetic heterogeneity.
2001 Nov
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
Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells.
2001 Oct
Effects of incubator humidity and hen age on yolk composition in broiler hatching eggs from young breeders.
2001 Oct
Ethanol- and nicotine-induced membrane changes in embryonic and neonatal chick brains.
2001 Oct
Deletion of N-terminal myristoylation site of HIV Nef abrogates both MHC-1 and CD4 down-regulation.
2001 Oct 1
Site-directed mutagenesis of the putative distal helix of peroxygenase cytochrome P450.
2001 Oct 1
Phosphorylation of human N-myristoyltransferase by N-myristoylated SRC family tyrosine kinase members.
2001 Oct 19
The biology and enzymology of protein N-myristoylation.
2001 Oct 26
Rational design of diflunisal analogues with reduced affinity for human serum albumin.
2001 Oct 31
Propranolol increases phosphatidic acid level via activation of phospholipase D.
2001 Sep
Rat pancreatic acinar cells express a cytosolic phospholipase D1b isoform that is not regulated by cholecystokinin.
2001 Sep
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 Sep 14
Optimization of carbohydrate fatty acid ester synthesis in organic media by a lipase from Candida antarctica.
2001 Sep 20
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 Sep 28
Coexpression of proteins with methionine aminopeptidase and/or N-myristoyltransferase in Escherichia coli to increase acylation and homogeneity of protein preparations.
2002
Differential use of myristoyl groups on neuronal calcium sensor proteins as a determinant of spatio-temporal aspects of Ca2+ signal transduction.
2002 Apr 19
Myristoylated alanine-rich C kinase substrate (MARCKS) sequesters spin-labeled phosphatidylinositol 4,5-bisphosphate in lipid bilayers.
2002 Apr 19
Myristyl and palmityl acylation of pI 5.1 carboxylesterase from porcine intestine and liver.
2002 Feb
Differences in the fatty acid composition of larvae and metamorphosing sea lampreys, Petromyzon marinus.
2002 Feb
Oxidative stress induced cytokine production in isolated rat pancreatic acinar cells: effects of small-molecule antioxidants.
2002 Feb
Enzymatic reaction of hydrogen peroxide-dependent peroxygenase cytochrome P450s: kinetic deuterium isotope effects and analyses by resonance Raman spectroscopy.
2002 Feb 12
Serum free fatty acid pattern and risk of myocardial infarction: a case-control study.
2002 Jan
[Fatty acid-induced reversal of general anesthesia: chain length-dependence of antagonizing potencies of fatty acids].
2002 Jan
Differences in calmodulin and calmodulin-binding proteins in phasic and tonic smooth muscles.
2002 Jan
Permeation of a myristoylated dipeptide across the buccal mucosa: topological distribution and evaluation of tissue integrity.
2002 Jan 1
Interaction of bovine (BSA) and human (HSA) serum albumins with ionic surfactants: spectroscopy and modelling.
2002 Jan 31
The linker domain of the Ha-Ras hypervariable region regulates interactions with exchange factors, Raf-1 and phosphoinositide 3-kinase.
2002 Jan 4
Patents

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 Sat Jun 26 02:52:12 UTC 2021
Edited
by admin
on Sat Jun 26 02:52:12 UTC 2021
Record UNII
0I3V7S25AW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
FEMA NO. 2764
Code English
N-TETRADECAN-1-OIC ACID
Common Name English
MYRISTIC ACID [INCI]
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 Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
CFR 21 CFR 172.860
Created by admin on Sat Jun 26 02:52:12 UTC 2021 , Edited by admin on Sat Jun 26 02:52:12 UTC 2021
NCI_THESAURUS C68388
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
LOINC 75103-2
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
CFR 21 CFR 357.210
Created by admin on Sat Jun 26 02:52:12 UTC 2021 , Edited by admin on Sat Jun 26 02:52:12 UTC 2021
LOINC 35157-7
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
JECFA EVALUATION MYRISTIC ACID
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
LOINC 47783-6
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
DSLD 3280 (Number of products:15)
Created by admin on Sat Jun 26 02:52:12 UTC 2021 , Edited by admin on Sat Jun 26 02:52:12 UTC 2021
Code System Code Type Description
EVMPD
SUB128589
Created by admin on Sat Jun 26 02:52:12 UTC 2021 , Edited by admin on Sat Jun 26 02:52:12 UTC 2021
PRIMARY
PUBCHEM
11005
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY
MERCK INDEX
M7689
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY Merck Index
CAS
544-63-8
Created by admin on Sat Jun 26 02:52:12 UTC 2021 , Edited by admin on Sat Jun 26 02:52:12 UTC 2021
PRIMARY
RXCUI
1356758
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY RxNorm
EPA CompTox
544-63-8
Created by admin on Sat Jun 26 02:52:12 UTC 2021 , Edited by admin on Sat Jun 26 02:52:12 UTC 2021
PRIMARY
DRUG BANK
DB08231
Created by admin on Sat Jun 26 02:52:12 UTC 2021 , Edited by admin on Sat Jun 26 02:52:12 UTC 2021
PRIMARY
ChEMBL
CHEMBL111077
Created by admin on Sat Jun 26 02:52:12 UTC 2021 , Edited by admin on Sat Jun 26 02:52:12 UTC 2021
PRIMARY
MESH
D019814
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY
WIKIPEDIA
MYRISTIC ACID
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY
NCI_THESAURUS
C68393
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-875-2
Created by admin on Sat Jun 26 02:52:12 UTC 2021 , Edited by admin on Sat Jun 26 02:52:12 UTC 2021
PRIMARY
FDA UNII
0I3V7S25AW
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY
USP_CATALOG
1448990
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY USP-RS
RXCUI
1313976
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY
HSDB
5686
Created by admin on Sat Jun 26 02:52:13 UTC 2021 , Edited by admin on Sat Jun 26 02:52:13 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
MAY BE PRESENT
USP
LIPID -> FATTY ACID
Values given are in undefined precent.
SALT/SOLVATE -> PARENT
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
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY