394580
Myristic anhydride
95%
Synonym(s):
Tetradecanoic anhydride
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About This Item
Linear Formula:
[CH3(CH2)12CO]2O
CAS Number:
Molecular Weight:
438.73
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
210-941-0
MDL number:
Assay:
95%
Form:
solid
InChI key
RCRYHUPTBJZEQS-UHFFFAOYSA-N
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
SMILES string
CCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCC
assay
95%
form
solid
mp
53-55 °C (lit.)
functional group
anhydride, ester
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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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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
Reactions of fatty acid chlorides. I. Preparation of fatty acid anhydrides.
Sonntag NOV, et al.
Journal of the American Oil Chemists' Society, 31(4), 151-157 (1954)
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)
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
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