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394580

Sigma-Aldrich

Myristic anhydride

95%

Synonym(s):

Tetradecanoic anhydride

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About This Item

Linear Formula:
[CH3(CH2)12CO]2O
CAS Number:
626-29-9
Molecular Weight:
438.73
EC Number:
210-941-0
MDL number:
MFCD00056151
UNSPSC Code:
12352100
PubChem Substance ID:
24864606
NACRES:
NA.22
form:
solid
Assay:
95%

Assay

95%

form

solid

mp

53-55 °C (lit.)

functional group

anhydride
ester

SMILES string

CCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCC

InChI

1S/C28H54O3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27(29)31-28(30)26-24-22-20-18-16-14-12-10-8-6-4-2/h3-26H2,1-2H3

InChI key

RCRYHUPTBJZEQS-UHFFFAOYSA-N

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General description

Myristic anhydride is an anhydride of myristic acid. Its synthesis by reacting myristoyl chloride with acetic anhydride has been reported. It participates in the synthesis of fatty acyl derivatives of macrocyclic peptides.

Application

Myristic anhydride may be used in the following studies:
  • As a reactant to synthesize cholesteryl myristate by reacting with cholesterol.
  • As a reactant in the synthesis of 1,2-dimyristoyl-sn-glycero-3-phosphocholine by acylating sn-glycero-3-phosphocholine.
  • As a reagent in the synthesis of 3-(bis-{2-(tert-butyldimethylsilyloxy)ethyl}amino)propane-1,2-diol, an intermediate of cationic lipid.
  • As a reactant to synthesize neryl myristate by reacting with nerol.
  • As a reagent to synthesize myristoylated t-butylglutamic acid by myristoylation of γ-tert-butoxy-glutamic acid.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
13808CC
11507JG
10204KZ

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K M Patel et al.
Journal of lipid research, 20(5), 674-677 (1979-07-01)
A high-yield synthesis of saturated, unsaturated, and short chain phosphatidylcholines from sn-glycero-3-phosphocholine is described. The procedure offers advantages over other reported procedures for the synthesis of phosphatidylcholine in that the large-scale synthesis and purification can be achieved in a minimum
Neryl myristate from the acarid mite, Aleuroglyphus ovatus (acarina, acaridae).
Leal WS, et al.
Agricultural and Biological Chemistry, 52(5), 1299-1300 (1988)
Bhupender S Chhikara et al.
Tetrahedron letters, 53(39), 5335-5337 (2012-11-24)
Designing microbicidal gels of anti-HIV drugs for local application to prevent HIV infection is a subject of major interest. 3'-Fluoro-3'-deoxythymidine (FLT), a nucleoside reverse transcriptase inhibitor (NRTI), was conjugated with a N-myristoyl glutamate scaffold. The conjugate showed gelation at 1%
Synthesis of saturated, unsaturated, spin-labeled, and fluorescent cholesteryl esters: Acylation of cholesterol using fatty acid anhydride and 4-pyrrolidinopyridine.
Patel KM, et al.
Lipids, 14(9), 816-818 (1979)
Michael H Nantz et al.
Molecular pharmaceutics, 7(3), 786-794 (2010-03-18)
We, and others, have observed that the structure of cationic lipids appears to have a significant effect on the transfection efficacy of optimized nucleic acid/cationic lipid complexes (lipoplexes) used for in vitro and in vivo gene delivery and expression. Although
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