Myristic Acid

Base Information

• Chemical Name: Myristic Acid
• CAS No.: 544-63-8
• Deprecated CAS: 45184-05-2
• Molecular Formula: C14H28O2
• Molecular Weight: 228.375
• Hs Code.: 29159080
• European Community (EC) Number: 208-875-2,636-389-4
• NSC Number: 5028
• UNII: 0I3V7S25AW
• DSSTox Substance ID: DTXSID6021666
• Nikkaji Number: J4.411C
• Wikipedia: Myristic_acid
• Wikidata: Q422658
• NCI Thesaurus Code: C68393
• RXCUI: 1356758
• Pharos Ligand ID: H41FYBJ298K3
• Metabolomics Workbench ID: 36
• ChEMBL ID: CHEMBL111077
• Mol file: 544-63-8.mol

Synonyms:Acid, Myristic;Acid, Tetradecanoic;Myristate;Myristic Acid;Tetradecanoic Acid

Chemical Property of Myristic Acid

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: <0.01 hPa (20 °C)
• Melting Point: 52-54 °C(lit.)
• Refractive Index: nD60 1.4305; nD70 1.4273
• Boiling Point: 319.639 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 144.777 °C
• PSA: 37.30000
• Density: 0.898 g/cm³
• LogP: 4.77210
• Storage Temp.: −20°C
• Solubility.: 1.07mg/l
• Water Solubility.: <0.1 g/100 mL at 18℃
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 12
• Exact Mass: 228.208930132
• Heavy Atom Count: 16
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

Tetradecanoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids,Other Classes -> Organic Acids
• Canonical SMILES: CCCCCCCCCCCCCC(=O)O
• Description: Myristic acid, also called tetradecanoic acid , is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. A myristate is a salt or ester of myristic acid. Myristic acid is named after the nutmeg Myristica fragrans. Nutmeg butter is 75 % trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butter fat and is a minor component of many other animal fats. It is also found in spermaceti, the crystallized fraction of oil from the sperm whale. Myristic acid is also commonly added co-translationally to the penultimate, nitrogen-terminus, glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. The myristic acid has a sufficiently high hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell. In this way, myristic acid acts as a lipid anchor in biomembranes. The ester isopropyl myristate is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired. Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol. Myristic acid is a 14-carbon saturated fatty acid. It is incorporated into myristoyl coenzyme A (myristoyl-CoA) and transferred by N-myristoyltransferase to the N-terminal glycine of certain proteins either during translation to modify protein activity or post-translationally in apoptotic cells.
• Uses: myristic acid is a surfactant and cleansing agent. When combined with potassium, myristic acid soap provides very good, abundant lather. This is a solid organic acid naturally occurring in butter acids such as nutmeg, oil of lovage, coconut oil, mace oil, and most animal and vegetable fats. Although some sources cite it as having no irritation potential, they do indicate comedogenicity potential. Myristic Acid is a fatty acid obtained from coconut oil and other fats. it has poor water solubility but is soluble in alcohol, chloro- form, and ether. it is used as a lubricant, binder, and defoaming agent. Myristic Acid is a common saturated fatty acid found in nutmeg, palm kernel oil, coconut oil and butter fat. Myristic acid is a 14-carbon saturated (14:0) fatty acid. In vivo, it is commonly added covalently to the N-terminus of proteins in a co-translational process termed N-myristoylation. In addition, there are examples where N-myristoylation occurs post-translationally, when a hidden myristoylation pattern is exposed.

Technology Process of Myristic Acid

There total 106 articles about Myristic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.3%

Ammonium myristate (16530-71-5) → n-tetradecanoic acid (544-63-8)

Guidance literature:

With hydrogenchloride; In water; pH=2;

Reference yield: 70.0%

myristylaldehyde (124-25-4,511542-15-7) → n-tetradecanoic acid (544-63-8)

Guidance literature:

With dihydrogen peroxide; 7-(trifluoromethyl)-1,10-ethyleneisoalloxazinium chloride; In water; acetonitrile; at 85 ℃; for 18h;

DOI:10.1021/ol301496m

Reference yield:

p-nitrophenyl myristate (14617-85-7) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + n-tetradecanoic acid (544-63-8)

Guidance literature:

With 4-(dialkylamino)pyridine linear oligomer ⁽⁴⁾ (n ca. 10); phosphate buffer pH 8.0; In methanol; at 30 ℃; Rate constant; other p-nitrophenyl alkanoates and 4-(dialkylamino)pyridines; dependence of reaction velocity on alkanoate chain length;

DOI:10.1021/ja00022a059

upstream raw materials:

octadec-4-enoic acid

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

1-decanoic acid

adipic acid monomethyl ester

Downstream raw materials:

myristic acid-(3-tetrahydro[2]furyl-propyl ester)

myristic acid-(1-methyl-3-tetrahydro[2]furyl-propyl ester)

myristic anhydride

N-(4-hydroxyphenyl)tetradecanamide

Refernces

• 1、 Zibuck, Regina,Seebach, Dieter. "24. Note on the Preparation of 1,2-Diketones from Acetylenes". . p. 237 - 240. Retrieved 1988.
• 2、 Siddiki,Rashed, Md. Nurnobi,Touchy, Abeda Sultana,Jamil, Md. A. R.,Jing, Yuan,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-Ichi. "Hydrolysis of amides to carboxylic acids catalyzed by Nb2O5". . p. 1949 - 1960. Retrieved 2021/03/26.
• 3、 Zorn, Katja,Oroz-Guinea, Isabel,Brundiek, Henrike,D?rr, Mark,Bornscheuer, Uwe T.. "Alteration of Chain Length Selectivity of Candida antarctica Lipase A by Semi-Rational Design for the Enrichment of Erucic and Gondoic Fatty Acids". . p. 4115 - 4131. Retrieved 2018/10/02.