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544-63-8

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544-63-8 Usage

Chemical Description

Myristic acid is a fatty acid that is also conjugated with glutamate ester to form myristoylated conjugates.

Chemical properties

Myristic acid appears as white to yellowish white solid, sometimes appearing as shiny crystalline solid, or white to yellowish white powder. It has a relative density of 0.8739 (80 ℃), melting point of 54.5 ℃ and the boiling point of 326.2 ℃. Its refractive index (nD60) is 1.4310. It is not soluble in water but soluble in ethanol, ether and chloroform. Myristin contains about 70% to 80% while other kinds of coconut oil, palm kernel oil also contain it.

Application

It can be used as a chemical agent, also for the synthesis of spices and organic matter It can be used in the manufacture of emulsifiers, waterproofing agents, curing agents, PVC heat stabilizers and plasticizers, and also used as the raw materials of spices and pharmaceutical. It is mainly used as raw materials for the production of surfactants for the production of sorbitan fatty acid esters, glycerol fatty acid esters, ethylene glycol or propylene glycol fatty acid esters. It can also be used for the production of isopropyl myristate and so on. It can also be used for defoamers and flavoring agent. According to the provision of China GB2760-89, it can be used to prepare a variety of food spices.

Preparation

Different sources of media describe the Preparation of 544-63-8 differently. You can refer to the following data:
1. To prepare the myristic acid, the methyl ester of the mixed fatty acids or mixed fatty acid methyl ester obtained from the coconut oil or palm kernel oil is subject to vacuum fractionation, obtaining myristic acid. For laboratory preparation, glycerol tris (tetradecanoate) is subject to saponification with 10% sodium hydroxide solution, further being acidified with hydrochloric acid to obtain the free myristic acid. It can also be made from tetradecanol.
2. From fatty acid mixture of palm seed oil

Toxicity

Natural fatty acids, non-toxic Can be safely used for food (FDA, § 172.860; 2000). LD50:43 mg/kg (mouse, transdermal).

Use limit

FEMA (mg/kg): soft drinks 5.3, cold drinks 2.6~10, candy 4.1, baked goods 5.3, pudding class 0.10.

Description

Different sources of media describe the Description of 544-63-8 differently. You can refer to the following data:
1. 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.
2. 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.

Chemical Properties

Different sources of media describe the Chemical Properties of 544-63-8 differently. You can refer to the following data:
1. Prepared from the fatty acid mixture of palm seed oil.
2. Myristic acid has a faint, waxy, oily odor
3. Myristic acid occurs as an oily white crystalline solid with a faint odor.

Occurrence

Reported found in nutmeg, palm seed, sperm whale oil, blue cheese, burley tobacco, cooked beef and chicken, fish, rum, apricot, banana, lemon and grapefruit juice, cranberry, guava, grapes, melon, papaya, raspberry, strawberry fruit and jam, cucumber, tomato, many cheeses, thyme, breads, butter, milk, lamb liver, pork, hop oil, beer, cognac, whiskies, peanut oil, cocoa, tea, coconut meat and milk, cloudberry, beans, passion fruit, mushroom, mango, starfruit, tamarind, kelp, cardamom, rice, buckwheat, watercress, malt, wort, loquat, Bourbon vanilla, lemon balm, shrimp, nectarine, crab, scallop, squid, cape gooseberry, Chinese quince, pawpaw and sweet grass oi

Uses

Different sources of media describe the Uses of 544-63-8 differently. You can refer to the following data:
1. 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.
2. 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.
3. Myristic Acid is a common saturated fatty acid found in nutmeg, palm kernel oil, coconut oil and butter fat.
4. 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.

Definition

ChEBI: A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.

Production Methods

Myristic acid occurs naturally in nutmeg butter and in most animal and vegetables fats. Synthetically, it may be prepared by electrolysis of methyl hydrogen adipate and decanoic acid or by Maurer oxidation of myristyl alcohol.

General Description

Oily white crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Myristic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Myristic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Fire Hazard

Myristic acid is probably combustible.

Pharmaceutical Applications

Myristic acid is used in oral and topical pharmaceutical formulations. Myristic acid has been evaluated as a penetration enhancer in melatonin transdermal patches in rats and bupropion formulations on human cadaver skin.Further studies have assessed the suitability of myristic acid in oxymorphone formulations and clobetasol 17-propionate topical applications.Furthermore, polyvinyl alcohol substituted with myristic acid (as well as other fatty acids) at different substitution degrees has been used for the preparation of biodegradable microspheres containing progesterone or indomethacin.

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 .

Safety Profile

Poison by intravenous route. Mutation data reported. An eye and human skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

Myristic acid is used in oral and topical pharmaceutical formulations and is generally regarded as nontoxic and nonirritant at the levels employed as an excipient. However, myristic acid is reported to be an eye and skin irritant at high levels and is poisonous by intravenous administration. Mutation data have also been reported. LD50 (mouse, IV): 0.043 g/kg LD50 (rat, oral): >10 g/kg

Purification Methods

Purify the acid via the methyl ester (b 153-154o/10mm, n25 1.4350), as for capric acid. [Trachtman & Miller J Am Chem Soc 84 4828 1962.] Also purify it by zone melting. It crystallises from pet ether, and is dried in a vacuum desiccator containing shredded wax. [Beilstein 2 IV 1126.]

Incompatibilities

Myristic acid is incompatible with strong oxidizing agents and bases.

Regulatory Status

GRAS listed. Included in the FDA Inactive Ingredients Database (oral capsules). Included in nonparenteral medicines licensed in the UK.

Check Digit Verification of cas no

The CAS Registry Mumber 544-63-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 4 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 544-63:
(5*5)+(4*4)+(3*4)+(2*6)+(1*3)=68
68 % 10 = 8
So 544-63-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)

544-63-8 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A12067)  Tetradecanoic acid, 98%   

  • 544-63-8

  • 250g

  • 209.0CNY

  • Detail
  • Alfa Aesar

  • (A12067)  Tetradecanoic acid, 98%   

  • 544-63-8

  • 500g

  • 309.0CNY

  • Detail
  • Alfa Aesar

  • (A12067)  Tetradecanoic acid, 98%   

  • 544-63-8

  • 2500g

  • 1323.0CNY

  • Detail
  • Sigma-Aldrich

  • (70079)  Myristicacid  analytical standard

  • 544-63-8

  • 70079-5G

  • 603.72CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1124)  Myristicacid  pharmaceutical secondary standard; traceable to USP

  • 544-63-8

  • PHR1124-1G

  • 732.19CNY

  • Detail
  • USP

  • (1448990)  Myristicacid  United States Pharmacopeia (USP) Reference Standard

  • 544-63-8

  • 1448990-200MG

  • 4,662.45CNY

  • Detail

544-63-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name tetradecanoic acid

1.2 Other means of identification

Product number -
Other names triacontyl alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Surfactants
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:544-63-8 SDS

544-63-8Synthetic route

1-bromo-octane
111-83-1

1-bromo-octane

6-bromohexanoic acid
4224-70-8

6-bromohexanoic acid

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
Stage #1: 1-bromo-octane With magnesium In tetrahydrofuran; ethylene dibromide at 60℃; for 0.5h; Inert atmosphere;
Stage #2: 6-bromohexanoic acid With 1-methyl-pyrrolidin-2-one; tert-butylmagnesium chloride In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere;
Stage #3: With buta-1,3-diene; nickel dichloride In tetrahydrofuran at 0℃; under 760.051 Torr; for 1h; Inert atmosphere;
99%
methyl myristoate
124-10-7

methyl myristoate

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With thiophene; aluminum tri-bromide for 1h; Ambient temperature;97.5%
Ethyl myristate
124-06-1

Ethyl myristate

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With thiophene; aluminum tri-bromide for 13h; Ambient temperature;95.5%
Ammonium myristate
16530-71-5

Ammonium myristate

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water pH=2;95.3%
1-pentadecene
13360-61-7

1-pentadecene

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With potassium permanganate; iron(III) chloride In acetone at -78 - 20℃;90%
Tetradecanoic acid 1-methylethyl ester
110-27-0

Tetradecanoic acid 1-methylethyl ester

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With thiophene; aluminum tri-bromide for 84h; Ambient temperature;87.5%
With sodium hydroxide In methanol; dichloromethane at 20℃; for 2h;
15-hydroxy-octacosan-14-one
5632-98-4

15-hydroxy-octacosan-14-one

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII); magnesium sulfate In acetonitrile for 8h; Heating;85%
myristanilide
622-56-0

myristanilide

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With niobium(V) oxide; water In neat (no solvent) for 20h; Reflux; Inert atmosphere;77%
C18H35N3O3

C18H35N3O3

A

acetic acid
64-19-7

acetic acid

B

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

C

ethyl azide
871-31-8

ethyl azide

Conditions
ConditionsYield
With ammonium hydroxide other reagents and conditions;A n/a
B n/a
C 75%
1-Tetradecanol
112-72-1

1-Tetradecanol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With peracetic acid; C24H29INO5 In acetic acid at 30℃; for 48h;75%
With Jones reagent In acetone at 20℃;
myristylaldehyde
124-25-4

myristylaldehyde

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; 7-(trifluoromethyl)-1,10-ethyleneisoalloxazinium chloride In water; acetonitrile at 85℃; for 18h;70%
With sodium dichromate; sulfuric acid In diethyl ether; water22.9%
With oxygen; Flavin mononucleotide; luciferase In aq. phosphate buffer Enzymatic reaction;
3-carbonyloxypropyonyl dodecanoyl peroxide
97499-84-8

3-carbonyloxypropyonyl dodecanoyl peroxide

A

n-Undecane
1120-21-4

n-Undecane

B

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
at -78℃; for 50h; Irradiation;A 1 % Chromat.
B 56%
pentadec-1-yne
765-13-9

pentadec-1-yne

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate In tetrachloromethane; water; acetonitrile for 3.5h; Ambient temperature;47%
octadec-4-enoic acid
21735-78-4

octadec-4-enoic acid

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With alkaline KMNO4
(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
123-78-4

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

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With chromic acid; acetic acid
1-decanoic acid
334-48-5

1-decanoic acid

adipic acid monomethyl ester
627-91-8

adipic acid monomethyl ester

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With methanol; sodium Electrolysis.anschliessende Hydrolyse;
hexadecan-2-one
18787-63-8

hexadecan-2-one

A

acetic acid
64-19-7

acetic acid

B

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
bei der Oxydation;
hexadeca-2-enoic acid
629-56-1

hexadeca-2-enoic acid

A

oxalic acid
144-62-7

oxalic acid

B

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
Ozonspaltung und Oxydation der Reaktionsprodukte mit KMnO4 in Aceton;
9-oxo-tetradecanoic acid
71173-32-5

9-oxo-tetradecanoic acid

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With hydrazine hydrate; diethylene glycol monosodium salt; diethylene glycol at 200℃;
5-oxotteradecanoic acid
16424-31-0

5-oxotteradecanoic acid

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With sodium 2-hydroxyethoxide; hydrazine hydrate; ethylene glycol
Stearolic acid
506-24-1

Stearolic acid

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With potassium hydroxide Schmelzen;
sebacic acid mono methyl ester
818-88-2

sebacic acid mono methyl ester

hexanoic acid
142-62-1

hexanoic acid

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With methanol; sodium Electrolysis.anschliessende Hydrolyse;
diethyl malonate
105-53-3

diethyl malonate

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
Ueber Dodecylmalonsaeure-diaethylester;
tetradecanoic acid N-(2-methylpropyl)amide
74420-88-5

tetradecanoic acid N-(2-methylpropyl)amide

A

isobutylamine hydrochloride
5041-09-8

isobutylamine hydrochloride

B

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 12h; Heating;
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid; ozone 1.) ether/methanol; Multistep reaction;
p-nitrophenyl myristate
14617-85-7

p-nitrophenyl myristate

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
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;
With N,N',N'',N'''-tetrakis-<10-decyl>-3,10,21,28-tetraoxo-2,11,20,29-tetra-aza<3.3.3.3>paracyclophane tetrachloride In ethanol; water at 30℃; Rate constant; other catalyst (three isomers containing two imidazolyl groups on adjacent and opposite alkyl chains); catalytic activity and substrate selectivity of both paracyclophanes compared; pH dependency of the substrate-binding ability of the cyclophanes;
With sodium phosphate buffer; Klebsiella sp. ZD112 pyrethroid-hydrolyzing esterase In acetonitrile at 30℃; pH=7.0; Enzyme kinetics;
(6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol 10-hexadecanoate
129436-86-8

(6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol 10-hexadecanoate

A

(2S,3S,5R)-5-[(1R)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol
89673-80-3, 148495-25-4, 74350-84-8

(2S,3S,5R)-5-[(1R)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol

B

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

C

1-hexadecylcarboxylic acid

1-hexadecylcarboxylic acid

D

Conditions
ConditionsYield
With sodium hydroxide In methanol for 2h; Heating; Further byproducts given;

A

(2S,3S,5R)-5-[(1R)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol
89673-80-3, 148495-25-4, 74350-84-8

(2S,3S,5R)-5-[(1R)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol

B

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

C

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

D

stearic acid
57-11-4

stearic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol for 2h; Heating; Further byproducts given;
dimyristoylphosphatidylcholine
18194-24-6

dimyristoylphosphatidylcholine

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
In various solvent(s) at 37℃; for 0.0833333h; Product distribution; PLase A2, tris (pH=7.8), hydrolysis, various amounts of PLase A2 (also with various amounts of coenzyme Q10);
tetradecanoic acid-nicotinamide complex
107864-43-7

tetradecanoic acid-nicotinamide complex

A

nicotinamide
98-92-0

nicotinamide

B

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Conditions
ConditionsYield
In various solvent(s) at 37℃; pH 1.2; nicotinamide release rate;
In various solvent(s) at 37℃; Kinetics; ΔG(excit.);
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

N-succinimidyl myristate
69888-86-4

N-succinimidyl myristate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In acetonitrile for 1.5h;100%
With dicyclohexyl-carbodiimide In ethyl acetate for 6h;98%
With dicyclohexyl-carbodiimide In ethyl acetate Ambient temperature;88%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

N-tetradecanoyloxysuccinimide

N-tetradecanoyloxysuccinimide

Conditions
ConditionsYield
With 2`,3`-dideoxycytidine In tetrahydrofuran for 12h; Ambient temperature;100%
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

monomethoxy poly(ethylene glycol)

monomethoxy poly(ethylene glycol)

tetradecanoic acid monomethoxy poly(ethylene glycol) ester

tetradecanoic acid monomethoxy poly(ethylene glycol) ester

Conditions
ConditionsYield
With camphor sulphuric acid for 18h; Heating;100%
(2S)-3-(benzyloxy)propane-1,2-diol
17325-85-8

(2S)-3-(benzyloxy)propane-1,2-diol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

1,2-di-O-myristoyl-3-O-benzyl-sn-glycerol
73083-33-7

1,2-di-O-myristoyl-3-O-benzyl-sn-glycerol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h;100%
C42H69N5O19
1360882-29-6

C42H69N5O19

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

C56H95N5O20
1360882-30-9

C56H95N5O20

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;100%
tetradecylamine
2016-42-4

tetradecylamine

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

N-tetradecyltetradecanamide

N-tetradecyltetradecanamide

Conditions
ConditionsYield
Stage #1: n-tetradecanoic acid With oxalyl dichloride; N,N-dimethyl-formamide In benzene at 20 - 60℃; for 2h;
Stage #2: tetradecylamine With triethylamine In benzene at 10 - 20℃;
100%
Stage #1: n-tetradecanoic acid With oxalyl dichloride In N,N-dimethyl-formamide; benzene at 20 - 60℃; for 2h;
Stage #2: tetradecylamine With triethylamine In benzene at 10 - 20℃;
100%
1-(tert-butyl-dimethyl-silanyloxy)propane-1,2-diol
85951-08-2

1-(tert-butyl-dimethyl-silanyloxy)propane-1,2-diol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

1-(tert-butyl)dimethylsilyl-2,3-dimyristoyl glycerol
56176-80-8

1-(tert-butyl)dimethylsilyl-2,3-dimyristoyl glycerol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 14h; Inert atmosphere; Cooling with ice;100%
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

1-ethyl-3-methyl-1H-imidazol-3-ium methylcarbonate

1-ethyl-3-methyl-1H-imidazol-3-ium methylcarbonate

C6H11N2(1+)*C14H27O2(1-)

C6H11N2(1+)*C14H27O2(1-)

Conditions
ConditionsYield
In methanol at 40℃;100%
lauric acid
143-07-7

lauric acid

trichlorovinylsilane
75-94-5

trichlorovinylsilane

Octanoic acid
124-07-2

Octanoic acid

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

C36H68O6Si
1330066-17-5

C36H68O6Si

Conditions
ConditionsYield
In toluene at 60 - 150℃; for 4h;99.82%
1-Hexadecanol
36653-82-4

1-Hexadecanol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

tetradecanoic acid hexadecyl ester
2599-01-1

tetradecanoic acid hexadecyl ester

Conditions
ConditionsYield
With zirconium(IV) oxychloride In 1,3,5-trimethyl-benzene at 162℃; for 24h;99.5%
With choline chloride; zinc(II) chloride at 110℃; for 10h;99%
With toluene-4-sulfonic acid; benzene at 130 - 140℃;
methanol

methanol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

methyl myristoate
124-10-7

methyl myristoate

Conditions
ConditionsYield
With modification of hypercrosslinked supermicroporous polymer (HMP-1) via sulfonation (HMP-1-SO3H) at 24.84℃; for 10h; Green chemistry;99%
With tert.-butylnitrite at 40℃; for 48h;99%
polyaniline sulfate at 70℃; for 24h;98%
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

1,2-O-isopropylidene-D-glycerol
14347-78-5

1,2-O-isopropylidene-D-glycerol

tetradecanoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester
163432-14-2

tetradecanoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 15℃; for 16h; Heating;99%
With dmap; dicyclohexyl-carbodiimide In chloroform for 16h; Ambient temperature;90%
Ergosterol
57-87-4

Ergosterol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

C42H70O2
23637-23-2

C42H70O2

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 12h; Reflux;99%
1-O-undec-10-ynyl-3-O-(4,4'-dimethoxytrityl)-sn-glycerol
1146526-53-5

1-O-undec-10-ynyl-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

1-O-undec-10-ynyl-2-O-myristoyl-3-O-(4,4'-dimethoxytrityl)-sn-glycerol
1146526-55-7

1-O-undec-10-ynyl-2-O-myristoyl-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

Conditions
ConditionsYield
Stage #1: n-tetradecanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.25h;
Stage #2: 1-O-undec-10-ynyl-3-O-(4,4'-dimethoxytrityl)-sn-glycerol In dichloromethane at 20℃; for 2h;
99%
thorium(IV) tetra-acetate
13075-28-0

thorium(IV) tetra-acetate

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

thorium myristate

thorium myristate

Conditions
ConditionsYield
In toluene byproducts: CH3COOH; soln. of myristic acid in toluene was added to soln. of Th(OAc)4 in toluene, refluxed for 40 h with azeotropic fractionation of liberated aceticacid and toluene (b.p. 106-110°C); evapd. in vac., dried in vac., elem. anal.;99%
1,3-dibutanoyloxy-2-propanol
17364-00-0

1,3-dibutanoyloxy-2-propanol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

2-(tetradecanoyloxy)propane-1,3-diyl dibutyrate
205873-03-6

2-(tetradecanoyloxy)propane-1,3-diyl dibutyrate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 0℃; for 4h;99%
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Isosorbide
652-67-5

Isosorbide

Tetradecanoic acid (3R,3aR,6S,6aR)-6-tetradecanoyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

Tetradecanoic acid (3R,3aR,6S,6aR)-6-tetradecanoyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

Conditions
ConditionsYield
With antimony triglycolate at 180℃; for 8h; Inert atmosphere;99%
1-octadecanol
112-92-5

1-octadecanol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

octadecyl myristate
3234-81-9

octadecyl myristate

Conditions
ConditionsYield
With triphenylphosphine-sulfur trioxide adduct In neat (no solvent) at 110℃; for 2h; Green chemistry;99%
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

2,2,2-trifluoroethyl tetradecanoate

2,2,2-trifluoroethyl tetradecanoate

Conditions
ConditionsYield
With sulfuric acid In cyclohexane at 100℃; for 12h;99%
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

tetradecanamide
638-58-4

tetradecanamide

Conditions
ConditionsYield
With ammonia; zircornium(IV) n-propoxide at 165℃; for 9h; Reagent/catalyst;98.9%
With ammonia at 190 - 210℃;
Multi-step reaction with 2 steps
1: phosphorus trichloride
2: ammonia / 0 °C
View Scheme
ethanol
64-17-5

ethanol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

Ethyl myristate
124-06-1

Ethyl myristate

Conditions
ConditionsYield
With sulfuric acid for 4.5h; Sonication;98.43%
With hydrogenchloride; calcium chloride In ethanol for 0.333333h;95%
With cerium(III) trislaurylsulfonate monohydrate In neat (no solvent) at 80℃; for 6h;93%
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

tetradecanoyl chloride
112-64-1

tetradecanoyl chloride

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide at -5 - 70℃; for 4.33333h;98.1%
With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 24h;95%
With thionyl chloride In chloroform at 65℃; Inert atmosphere;93%
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

myristic anhydride
626-29-9

myristic anhydride

Conditions
ConditionsYield
With acetic anhydride at 140℃; for 0.5h;98%
at 340℃;
With acetic anhydride Erhitzen unter Ausschluss der Luftfeuchtigkeit zu schwachem Sieden;
With 1,1'-carbonyldiimidazole In chloroform for 5h; Ambient temperature;
Multi-step reaction with 2 steps
1: phosphorus (III)-chloride
View Scheme
allyl 6-O-benzyl-4-O-benzyloxycarbonylmethyl-3-O-((R)-3-hydroxytetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
927175-37-9

allyl 6-O-benzyl-4-O-benzyloxycarbonylmethyl-3-O-((R)-3-hydroxytetradecanoyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

allyl 6-O-benzyl-4-O-benzyloxycarbonylmethyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarboylamino)-α-D-glucopyranoside
927175-38-0

allyl 6-O-benzyl-4-O-benzyloxycarbonylmethyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarboylamino)-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;98%
1-O-(10-(cyclooct-2-ynyloxy)decanoyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol
1146526-65-9

1-O-(10-(cyclooct-2-ynyloxy)decanoyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

1-O-(10-(cyclooct-2-ynyloxy)decanoyl)-2-O-myristoyl-3-O-(4,4'-dimethoxytrityl)-sn-glycerol
1146526-67-1

1-O-(10-(cyclooct-2-ynyloxy)decanoyl)-2-O-myristoyl-3-O-(4,4'-dimethoxytrityl)-sn-glycerol

Conditions
ConditionsYield
Stage #1: n-tetradecanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.25h;
Stage #2: 1-O-(10-(cyclooct-2-ynyloxy)decanoyl)-3-O-(4,4'-dimethoxytrityl)-sn-glycerol In dichloromethane at 20℃; for 2h;
98%
L-homoserine lactone hydrochloride
2185-03-7

L-homoserine lactone hydrochloride

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

(S)-N-tetradecanoyl-homoserine lactone

(S)-N-tetradecanoyl-homoserine lactone

Conditions
ConditionsYield
Stage #1: n-tetradecanoic acid With sodium hydroxide In water pH=9;
Stage #2: L-homoserine lactone hydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; for 24h;
98%
(S)-(-)-α-amino-γ-butyrolactone hydrobromide
6305-38-0, 15295-77-9, 67580-93-2, 110045-70-0

(S)-(-)-α-amino-γ-butyrolactone hydrobromide

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

(S)-N-tetradecanoyl-homoserine lactone

(S)-N-tetradecanoyl-homoserine lactone

Conditions
ConditionsYield
Stage #1: n-tetradecanoic acid With sodium hydroxide In water pH=9;
Stage #2: (S)-(-)-α-amino-γ-butyrolactone hydrobromide With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; for 24h;
98%
3-O-(2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl)-sn-glycerol
1236037-89-0

3-O-(2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl)-sn-glycerol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

3-O-(2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl)-1,2-di-O-myristoyl-sn-glycerol
1236037-90-3

3-O-(2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl)-1,2-di-O-myristoyl-sn-glycerol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane98%
(20R)-6β-methoxy-20-methyl-3α,5α-cyclopregnane-16β,17α,21-triol 16-O-{2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-4'-O-triethylsilyl-α-L-arabinopyranoside}

(20R)-6β-methoxy-20-methyl-3α,5α-cyclopregnane-16β,17α,21-triol 16-O-{2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-4'-O-triethylsilyl-α-L-arabinopyranoside}

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

(20R)-21-O-tetradecanoyl-20-methyl-6β-methoxy-3α,5α-cyclopregnan-16β,17α,21-triol 16-O-{2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-4'-O-triethylsilyl-α-L-arabinopyranoside}

(20R)-21-O-tetradecanoyl-20-methyl-6β-methoxy-3α,5α-cyclopregnan-16β,17α,21-triol 16-O-{2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-4'-O-triethylsilyl-α-L-arabinopyranoside}

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;98%

544-63-8Relevant articles and documents

Isolation of a lupane triterpene fatty acid ester with antibacterial activity from the leaves of Finlaysonia obovata

Mishra, Pravat Manjari,Sree,Panigrahi, Mallika

, p. 161 - 163 (2012)

-

Long-chain fatty acid acylated derivatives of isoflavone glycosides from the rhizomes of Iris domestica

Li, Jiayuan,Liu, Yanfei,Ni, Gang,Wang, Renzhong,Yu, Dequan

, (2021/11/01)

Six undescribed long-chain fatty acid esters of isoflavone glycosides were obtained from the rhizomes of Iris domestica (L.). Their structures were elucidated by comprehensive spectroscopic data, alkaline hydrolysis, and acid hydrolysis. This is the first report of the long-chain (C14–C18) fatty acid derivatives of isoflavone glycosides from natural products. Belamcandnoate B and D exhibited moderate cytotoxic activities against HCT-116, HepG2, and BGC823 cell lines with IC50 values of 1.69–6.86 μM. Belamcandnoate B and E exhibited 72.27 and 58.98% inhibitory activities, respectively, against Fe2+/cysteine-induced liver microsomal lipid peroxidation at a concentration of 10 μM.

Highly luminescent and multi-sensing aggregates co-assembled from Eu-containing polyoxometalate and an enzyme-responsive surfactant in water

Lei, Nana,Shen, Dazhong,Chen, Xiao

, p. 399 - 407 (2019/01/24)

Hybrid co-assembly of polyoxometalates (POMs) with cationic organic matrices offers a preferable way to greatly enhance POM functionality as well as processability. Thus, multi-stimulus responsive supramolecular materials based on lanthanide-containing POMs with improved luminescence may be fabricated from appropriate components through this convenient strategy. Herein, we reported that the co-assembly of Na9(EuW10O36)·32H2O (EuW10) and a commercially available cationic surfactant, myristoylcholine chloride (Myr), in water could produce enhanced red-emitting luminescent aggregates, with their photophysical properties highly dependent on the molar ratio (R) between Myr and EuW10. The R of 36 was finally selected owing to the displayed superior luminescence intensity and good aggregate stability. The Myr/EuW10 hybrids induced by electrostatic and hydrophobic forces presented practically as multilamellar spheres with diameters varying from 80 to 300 nm. Compared to an aqueous solution of EuW10 nanoclusters, a 12-fold increase in absolute luminescence quantum yield (~23.3%) was observed for the hybrid spheres, which was ascribed to the efficient shielding of water molecules. An unusual aggregation arrangement mechanism and the excellent photophysical properties of these aggregates were thoroughly investigated. Both the enzyme substrate character of Myr and the sensitive coordination structure of EuW10 to the surrounding environment made Myr/EuW10 aggregates exhibit multi-stimulus responsiveness to enzymes, pH, and transition metal ions, thus providing potential applications in fluorescence sensing, targeted-release, and optoelectronics.

CERAMIDE DERIVATIVES AS ANTICANCER AGENTS

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Page/Page column 22; 23, (2017/02/09)

The invention provides a compound of formula (I): (I) wherein R1-R4 have any of the values defined in the specification, as well as compositions comprising a compound of formula (I) and methods for treating diseases (e.g. cancer).

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