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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

Myristic acid was discovered in the nutmeg that is the seed of the tropical tree Myristica fragrans. It is a saturated fatty acid member of the sub-group called long-chain fatty acids. It occurs, as glycerol ester, in most animal and vegetable fats and oils. It is mostly found in milk fat. Myristic acid is hypercholesterolemic and raises both LDL and HDL cholesterol concentrations compared with oleic acid in healthy subjects. Myristic acid delays gastric emptying. It may act as a trigger, for the release of a hormone or hormones, which can delay gastric emptying. It is used as ingredient in soaps, cosmetic and shaving creams, often in the form of the ester isopropyl myristate. It is safe as cosmetic ingredients in the current practices of use and concentration.

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
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.
1999 Jul 14
Adipose tissue fatty acids in men from two populations with different cardiovascular risk: the LiVicordia study.
1999 May
Evaluation of skin damage caused by percutaneous absorption enhancers using fractal analysis.
2000 Apr
Molecular cloning, genomic organization, and biochemical characterization of myristoyl-CoA:protein N-myristoyltransferase from Arabidopsis thaliana.
2000 Mar 31
Comparative quantitative fatty acid analysis of triacylglycerols using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and gas chromatography.
2001
Functional analysis of ADP-ribosylation factor (ARF) guanine nucleotide exchange factors Gea1p and Gea2p in yeast.
2001
Fatty acid synthesis in African trypanosomes: a solution to the myristate mystery.
2001 Aug
Pre-steady-state kinetic studies of Saccharomyces cerevisiae myristoylCoA:protein N-myristoyltransferase mutants identify residues involved in catalysis.
2001 Aug 7
Characterization of the binding of Photobacterium phosphoreum P-flavin by Vibrio harveyi Luciferase.
2001 Dec 15
Cellular and viral Fos proteins are degraded by different proteolytic systems.
2001 Feb 22
Characterization of a new member of the fatty acid-binding protein family that binds all-trans-retinol.
2001 Jan 12
The kinetic and spectral characterization of the E. coli-expressed mammalian CYP4A7: cytochrome b5 effects vary with substrate.
2001 Jan 15
[Determination of higher fatty acids in human plasma].
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
Crystal structure analysis of warfarin binding to human serum albumin: anatomy of drug site I.
2001 Jun 22
Self-assembly of regular hollow icosahedra in salt-free catanionic solutions.
2001 Jun 7
Imidazoline I(1) receptor-induced activation of phosphatidylcholine-specific phospholipase C elicits mitogen-activated protein kinase phosphorylation in PC12 cells.
2001 Mar
Regulation of G proteins by covalent modification.
2001 Mar 26
Ca(2+)- and myristoylation-dependent association of calcineurin with phosphatidylserine.
2001 May
A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, designed by prediction of the fluorescence intensity.
2001 May 15
Biochemical characterization of the reverse activity of rat brain ceramidase. A CoA-independent and fumonisin B1-insensitive ceramide synthase.
2001 May 18
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
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
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
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 use of myristoyl groups on neuronal calcium sensor proteins as a determinant of spatio-temporal aspects of Ca2+ signal transduction.
2002 Apr 19
Intrastriatal injection of sonic hedgehog reduces behavioral impairment in a rat model of Parkinson's disease.
2002 Jan
Differences in calmodulin and calmodulin-binding proteins in phasic and tonic smooth muscles.
2002 Jan
Mechanisms of competitive adsorption of albumin and sodium myristate at the silicon oxide/aqueous interface.
2005 Oct 25
Single-step purification of myristoylated and nonmyristoylated recoverin and substrate dependence of myristoylation level.
2006 Feb 1
Self assembly of anastomosis-like superstructures in fatty acid/guanidine hydrochloride aqueous dispersions.
2010 Jan 15
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:34:52 UTC 2023
Edited
by admin
on Wed Jul 05 22:34:52 UTC 2023
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
MYRISTATE
Common Name 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 Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
CFR 21 CFR 172.860
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
NCI_THESAURUS C68388
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
LOINC 75103-2
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
CFR 21 CFR 357.210
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
LOINC 35157-7
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
JECFA EVALUATION MYRISTIC ACID
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
LOINC 47783-6
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
DSLD 3280 (Number of products:15)
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
Code System Code Type Description
SMS_ID
100000154392
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
EVMPD
SUB128589
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
PUBCHEM
11005
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
MERCK INDEX
M7689
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY Merck Index
CAS
544-63-8
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
RXCUI
1356758
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID6021666
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
DRUG BANK
DB08231
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
RS_ITEM_NUM
1448990
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
CHEBI
30807
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL111077
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
CHEBI
28875
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
DAILYMED
0I3V7S25AW
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
MESH
D019814
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
WIKIPEDIA
MYRISTIC ACID
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
NCI_THESAURUS
C68393
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
NSC
5028
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-875-2
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
FDA UNII
0I3V7S25AW
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
RXCUI
1313976
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
ALTERNATIVE
HSDB
5686
Created by admin on Wed Jul 05 22:34:52 UTC 2023 , Edited by admin on Wed Jul 05 22:34:52 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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LIPID -> FATTY ACID
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY