MilliporeSigma
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70082

Sigma-Aldrich

Myristic acid

≥98.0% (GC)

Synonym(s):
Tetradecanoic acid, 1-Tridecanecarboxylic acid, NSC 5028, C14:0
Linear Formula:
CH3(CH2)12COOH
CAS Number:
Molecular Weight:
228.37
Beilstein:
508624
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥98.0% (GC)

form

powder

bp

250 °C/100 mmHg (lit.)

mp

52-54 °C (lit.)
53-56 °C

functional group

carboxylic acid

shipped in

ambient

storage temp.

room temp

SMILES string

CCCCCCCCCCCCCC(O)=O

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)

InChI key

TUNFSRHWOTWDNC-UHFFFAOYSA-N

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Biochem/physiol Actions

Myristic acid is commonly added via a covalent linkage to the N-terminal glycine of many eukaryotic and viral proteins, a process called myristoylation. Myristoylation enables proteins to bind to cell membranes and facilitates protein-protein interactions. Myristolyation of proteins affect many cellular functions and thus has implications in health and disease .

Storage Class Code

13 - Non Combustible Solids

WGK

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Dale D O Martin et al.
Biochimie, 93(1), 18-31 (2010-11-09)
Myristoylation corresponds to the irreversible covalent linkage of the 14-carbon saturated fatty acid, myristic acid, to the N-terminal glycine of many eukaryotic and viral proteins. It is catalyzed by N-myristoyltransferase. Typically, the myristate moiety participates in protein subcellular localization by
S Curry et al.
Biochimica et biophysica acta, 1441(2-3), 131-140 (1999-11-26)
Human serum albumin possesses multiple fatty acid binding sites of varying affinities, but the precise locations of these sites have remained elusive. The determination of the crystal structure of human serum albumin complexed with myristic acid recently revealed the positions
Anja Meier et al.
Hepatology (Baltimore, Md.), 58(1), 31-42 (2012-12-06)
Chronic infection with the human hepatitis B virus (HBV) is a global health problem and a main cause of progressive liver diseases. HBV exhibits a narrow host range, replicating primarily in hepatocytes. Both host and hepatocyte specificity presumably involve specific
Dalit Shental-Bechor et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(44), 17839-17844 (2012-08-01)
We present an integrated experimental and computational study of the molecular mechanisms by which myristoylation affects protein folding and function, which has been little characterized to date. Myristoylation, the covalent linkage of a hydrophobic C14 fatty acyl chain to the
Geok-Lin Chua et al.
PloS one, 7(7), e41924-e41924 (2012-07-31)
Integrins are signal transducer proteins involved in a number of vital physiological processes including cell adhesion, proliferation and migration. Integrin molecules are hetero-dimers composed of two distinct subunits, α and β. In humans, 18 α and 8 β subunits are

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