59227-89-3

Basic information

• Product Name: Laurocapram
• Synonyms: n0252;n-laurylcaprolactam;tranzone;usafnd-72;AZONE;azon;LAUROCAPRAM;1-DODECYL AZACYCLOHEPTA-2-ONE
• CAS NO: 59227-89-3
• Molecular Formula: C₁₈H₃₅NO
• Molecular Weight: 281.48
• EINECS: 261-668-9
• Product Categories: ketone;Cosmetic;Pharmaceutical intermediates, pharmaceutical raw materials
• Mol File: 59227-89-3.mol

Chemical Properties

• Melting Point: -7°
• Boiling Point: bp50m 160°
• Flash Point: 165.2 °C
• Appearance: Colorless or yellowish transparent liquid
• Density: 0.906-0.926
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.470-1.473
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: -0.43±0.20(Predicted)
• Merck: 14,5385
• CAS DataBase Reference: Laurocapram(CAS DataBase Reference)
• NIST Chemistry Reference: Laurocapram(59227-89-3)
• EPA Substance Registry System: Laurocapram(59227-89-3)

Safety Data

• Safety Statements: 24/25
• RTECS: CM3995000
• Hazardous Substances Data: 59227-89-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Laurocapram is used as a pharmaceutic aid (excipient) for its ability to act as an inert substance, ensuring the shelf-life of active ingredients is long enough for internal use.
Used in Cosmetic and Personal-Care Industry:
Laurocapram is used as a penetration enhancer in cosmetic preparations and personal-care products, improving the absorption of active ingredients into the skin.
Used in Pesticides:
Laurocapram is used as a pro-absorbing agent and sterilization plant growth regulator, enhancing the effectiveness of pesticides by improving their penetration into plants.
Used in Leather Industry:
Laurocapram can be used as an accelerator in the coloring and dyeing of leather, improving the efficiency and quality of the process.
Used as Antifungal Lipopeptide:
Laurocapram has applications in the development of antifungal agents, particularly in the form of lipopeptides, which can be effective against various fungal infections.

Penetration enhancer

Laurocapram, also known as azone, lauric Lun, N-lauryl caprolactam, quinacridone, nitrogen ketone. Its chemical name is 1-n-dodecyl azetidin-2-one, which is a new high security penetration enhancer. It is colorless transparent liquid at room temperature, slightly viscous, odorless. It can form emulsion with water, soluble in various organic solvents, and it has good lubricity, which promote the hydrophilic and lipophilic drug product activity or cosmetics nutrients to penetrate into the skin, greatly reducing the drug remain time in the stratum corneum, significantly enhancing drug efficacy and cosmetic results. Thus, we can reduce the amount of primary medical and reduce costs. Azone transdermal absorption enhancing effect lags behind. Laurocapram on hydrophilic and lipophilic drugs have significantly transdermal Aided role.? It has good aided effect on many kinds of plant extracts in emulsion state or colloidal state, and alkaloids effect is particularly evident. Transdermal penetration is stronger than dimethyl sulfoxide. 8-bromo cyclic nucleotide containing 1% azone permeability effect is equivalent to 12 times the 50% dimethyl sulfoxide. Often in combination with propylene glycol, synergy, the best use of transdermal concentration of 0.1% to 5%, safe and low toxic, non-irritating. The chemical property is stable, and it is kept up to four years at the room temperature. It can be considered a decyl methyl sulfoxide with pyrrolidone composite for good novel penetration enhancers, skin irritation. It can promote the drug through the skin barrier corticosteroids, indomethacin, fluorouracil, hydroquinone and many other drugs transdermal absorption, improving local and systemic blood concentration, and improving the bioavailability of the drug. Lipophilic, they have transdermal effect for hydrophilic drugs. It can soften the skin and enhance its permeability. They have anti-inflammatory, analgesic and anti-itching effect. Low toxicity, oral LD50> 7g/kg, it is not compatible with strong acids or Vaseline to avoid reduce the effect.

References

http://www.chemicalland21.com/lifescience/foco/LAUROCAPRAM.htm

InChI:InChI=1/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-13-16-19-17-14-12-15-18(19)20/h2-17H2,1H3

Synthetic route

caprolactam (105-60-2) + 1-dodecylbromide (143-15-7) → Azone (59227-89-3)

Conditions	Yield
With sodium hydroxide In water; toluene	99.6%
With sodium hydroxide In toluene	95%
With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate In cyclohexane	92.8%

1-chlorododecane (112-52-7) → Azone (59227-89-3)

Conditions	Yield
	95.2%

caprolactam (105-60-2) → Azone (59227-89-3)

Conditions	Yield
With sodium; xylene anschliessend mit Dodecylbromid;

1-dodecyl alcohol (112-53-8) → Azone (59227-89-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / 48percent aq. HBr / dodecylpyridinium bromide / 1.5 h / Irradiation 2: 87 percent / NaOH / n-C12H25N(CH3)3Br / 9 h / 70 - 75 °C View Scheme

caprolactam (105-60-2) + tert-butyl methyl ether (1634-04-4) + 1-dodecylbromide (143-15-7) → Azone (59227-89-3)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide

sodium oxide (Na2 O) + 1-dodecylbromide (143-15-7) + 1-trimethylsilanyl-azepan-2-one (3553-94-4) → Azone (59227-89-3)

Conditions	Yield
In 1,2-dimethoxyethane

caprolactam (105-60-2) + pet + 1-dodecylbromide (143-15-7) → Azone (59227-89-3)

Conditions	Yield
In toluene; mineral oil

1-dodecylbromide (143-15-7) → Azone (59227-89-3)

Conditions	Yield
With sodium hydroxide; Aliquat 336 In toluene

caprolactam (105-60-2) + sodium hydride-mineral oil + 1-dodecylbromide (143-15-7) → Azone (59227-89-3)

Conditions	Yield
	60 g (80%)

4-toluenesulfonyl azide (941-55-9) + Azone (59227-89-3) → C25H42N2O2S

Conditions	Yield
Stage #1: Azone With bis(triphenylphosphine)carbonyliridium(I) chloride; 1,1,3,3-Tetramethyldisiloxane In dichloromethane at 20℃; for 0.5h; Stage #2: 4-toluenesulfonyl azide In dichloromethane at 20℃; for 3h; chemoselective reaction;	70%

Azone (59227-89-3) → 6-dodecylamino-hexanoic acid (58157-72-5)

Conditions	Yield
With hydrogenchloride

Azone (59227-89-3) → (5-carboxy-pentyl)-dodecyl-dimethyl-ammonium; iodide

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated HCl 2: Na2CO3; methanol View Scheme

Azone (59227-89-3) → 3-bromo-1-dodecylazacycloheptan-2-one (114919-82-3)

Conditions	Yield
With phosphorus pentachloride; bromine In dichloromethane; chloroform

uranyl nirate hexahydrate + Azone (59227-89-3) → UO2(NO3)2(CH2(CH2)4CONC12H25)2 (147186-51-4)

Conditions	Yield
In nitric acid aq. HNO3; addn. of soln. of uranyl nitrate in aq. HNO3 to ligand in petroleum ether, shaking (several hours), pptn.; filtration, washing (water, petroleum ether), recrystn. (toluene), washing (petroleum ether), filtration, drying (vac.); elem. anal.;

Upstream product

• 105-60-2 caprolactam 
• 143-15-7 1-dodecylbromide 
• 112-53-8 1-dodecyl alcohol 
• 1634-04-4 tert-butyl methyl ether 
• 3553-94-4 1-trimethylsilanyl-azepan-2-one 
• 112-52-7 1-chlorododecane 

Relevant articles and documents

Process for the preparation of N-substituted lactams

The invention relates to a process for the preparation of N-substituted lactams by reaction of a lactam, which is unsubstituted on the nitrogen, with an organic halide in the presence of at least one solid-liquid phase transfer catalyst, such as a quaternary ammonium salt, and of at least one solid inorganic base, such as an alkali metal hydroxide, and in the absence of solvent. By this process, N-substituted lactams are obtained with good yields and high purity. The absence of solvent makes possible a considerable gain in productivity and an improvement in safety and in regard for the environment.

Syntheses of long-chain quaternary ammonium salts from fatty alcohols by microwave irradiation

The phase-transfer catalysts, long-chain quaternary ammonium salts, were rapidly synthesized from fatty alcohols by the reactions with hydrogen halides in the presence of trialkyl amines under microwave irradiation. The catalysts could be widely applied in a variety of quick and new organic reactions, whether by conventional heating or under microwave irradiation. The reaction efficiencies under microwave irradiation were higher than those obtained with conventional heating.

N-allyl-lactams as crystallization inhibitors

Crystallization of active material in spraying of an aqueous solution of certain specified fungicides is retarded by incorporation therein of an N-alkyl-lactam of the formula STR1 in which R represents alkyl having 6 to 18 carbon atoms and n represents the numbers 3, 4 or 5.

N-alkyl-lactams as crystallization inhibitors

In the spraying of an aqueous liquor comprising at least one of 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol and 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol, the improvement which comprises including in the liquor an N-alkyl-lactam of the formula STR1 in which R represents alkyl having 8 to 18 carbon atoms and n represents the numbers 3, 4 or 5,

Solid formulations

New solid formulations of A) at least one agrochemical active compound, B) at least one additive from the groups mentioned in the description, C) at least one dispersant, D) at least one carrier and E) if appropriate, further active compounds and/or additives, a process for preparing the solid formulations and their use for treating plants. A new device for preparing new granules.

Facilitated transport of two model steroids by esters and amides of clofibric acid

A series of novel dermal penetration enhancers, esters and amides of clofibric acid, was synthesized. The permeation parameters and skin retention of two steroids (hydrocortisone-21-acetate and betamethasone-17-valerate) in propylene glycol were studied with athymic nude mouse skin by in vitro diffusion cell techniques in the presence of the novel enhancer compounds. Isopropyl myristate, dimethyl lauramide, and 1-dodecylazacycloheptan-2-one (laurocapram, Azone) were used as control enhancers. The most satisfactory enhancement of both the ester and amide series was observed with clofibric acid octyl amide; coadministration increased skin retention of hydrocortisone acetate after 24 h by 3.5-fold and that of betamethasone valerate by 2.9- fold. Diffusion cell receptor concentrations increased 51.6- and 10.3-fold, respectively, during the same time period. However, the enhancer compound in this case was applied to the skin 1 h prior to each of the steroids. The amide analogues were more effective than the equivalent ester compounds of the same carbon chain length. The best enhancer compounds (2c, 3d, 3e, and 3f) were nonirritating to athymic mouse skin in vivo.

Process for the production of 1-n-dodecylazacycloheptan-2-one

There is disclosed a method for the production of 1-n-dodecylazacycloheptan-2-one by reacting caprolactam with 1-bromododecane in the presence of a phase transfer catalyst under anhydrous conditions using a nonpoisonous hydrocarbon as solvent. The method is a one-pot synthesis employing solid-liquid phase transfer catalysis.

Process for preparing 1-dodecylazacycloheptane-2-one

Disclosed is a process for preparing 1-dodecylazacyclo-heptane-2-one, the process comprising reacting azacylcloheptane-2-one with dodecyl halide in a substantially non-aqueous system in the presence of a phase-transfer catalyst represented by the formula STR1 wherein R1, R2, R3 and R4 are alkyl or aralkyl, or two or three of the groups R1, R2, R3 and R4, when taken together with nitrogen to which they are attached, form a heterocyclic group (in which case the remaining one or two of the groups being alkyl or aralkyl) and X? is a univalent anion.

Toxicity screening of N-alkylazacycloheptan-2-one derivatives in cultured human skin cells: Structure-toxicity relationships

A number of N-alkylazacycloheptan-2-one derivatives, with the hydrocarbon chain lengths systematically varied from C2 to C16, were tested for their possible skin toxic effects. For this purpose, three in vitro cytotoxicity assays were used: (1) inhibition of proliferation of cultured human fibroblasts and keratinocytes: (2) inhibition of collagen contraction by human fibroblasts; and (3) cell morphology changes in confluent cultures of human fibroblasts and keratinocytes. With all assays used, the toxicity of N-alkylazacycloheptan-2-one derivatives increased from C2 to C8, remained constant at a hydrocarbon chain length between C8 and C14, and subsequently decreased with increasing alkyl chain length. A similar trend has been observed for flux enhancement of nitroglycerine in the presence of these N-alkylazacycloheptan-2-one derivatives, suggesting that with these compounds a parallelism exists between skin cell toxicity and penetration enhancing capacity. Since for practical use it is preferable to find a balance between skin toxicity and the penetration enhancement effect of a particular enhancer, it would be advisable to do QSAR studies of this kind with a number of congeners of a particular compound in order to optimize the choice. In this particular case, further modification of the N-alkylazacycloheptan-2-one structure might lead to an even better choice than the often propagated dodecyl derivative.

Process for the preparation of 1-substituted aza-cycloalkan-2-ones

A process for the preparation of 1-substituted azacycloalkan-2-ones of the formula I STR1 in which R, m and n have the meanings indicated by reaction of corresponding 1-trimethylsilylazacycloalkan-2-ones with alkali metal alcoholate or alkali metal oxide and then alkylation of the alkali metal salts which are formed.