Product Name

  • Name

    Laurocapram

  • EINECS 261-668-9
  • CAS No. 59227-89-3
  • Article Data15
  • CAS DataBase
  • Density 0.895 g/cm3
  • Solubility Insoluble in water, and form emulsions with water, soluble in various organic solvents
  • Melting Point -7oC
  • Formula C18H35NO
  • Boiling Point 404.9 °C at 760 mmHg
  • Molecular Weight 281.482
  • Flash Point 165.2 °C
  • Transport Information
  • Appearance Colorless or yellowish transparent liquid
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 59227-89-3 (Laurocapram)
  • Hazard Symbols
  • Synonyms Laurocapramum;1-Dodecylazepan-2-one;2H-Azepin-2-one,1-dodecylhexahydro-;1-Dodecylazacycloheptan-2-one;2H-Azepin-2-one, 1-dodecylhexahydro-;N-Lauryl caprolactam;N 0252;Tranzone;1-Dodecyl azacyclohepta-2-one;N-Dodecylcaprolactam;Laurocapram Azone;
  • PSA 20.31000
  • LogP 5.24780

Synthetic route

caprolactam
105-60-2

caprolactam

1-dodecylbromide
143-15-7

1-dodecylbromide

Conditions
ConditionsYield
With sodium hydroxide In water; toluene99.6%
With sodium hydroxide In toluene95%
With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate In cyclohexane92.8%
1-chlorododecane
112-52-7

1-chlorododecane

Conditions
ConditionsYield
95.2%
caprolactam
105-60-2

caprolactam

Conditions
ConditionsYield
With sodium; xylene anschliessend mit Dodecylbromid;
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Conditions
ConditionsYield
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

caprolactam

tert-butyl methyl ether
1634-04-4

tert-butyl methyl ether

1-dodecylbromide
143-15-7

1-dodecylbromide

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide
sodium oxide (Na2 O)

sodium oxide (Na2 O)

1-dodecylbromide
143-15-7

1-dodecylbromide

1-trimethylsilanyl-azepan-2-one
3553-94-4

1-trimethylsilanyl-azepan-2-one

Conditions
ConditionsYield
In 1,2-dimethoxyethane
caprolactam
105-60-2

caprolactam

pet

pet

1-dodecylbromide
143-15-7

1-dodecylbromide

Conditions
ConditionsYield
In toluene; mineral oil
1-dodecylbromide
143-15-7

1-dodecylbromide

Conditions
ConditionsYield
With sodium hydroxide; Aliquat 336 In toluene
caprolactam
105-60-2

caprolactam

sodium hydride-mineral oil

sodium hydride-mineral oil

1-dodecylbromide
143-15-7

1-dodecylbromide

Conditions
ConditionsYield
60 g (80%)
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

C25H42N2O2S

C25H42N2O2S

Conditions
ConditionsYield
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%
6-dodecylamino-hexanoic acid
58157-72-5

6-dodecylamino-hexanoic acid

Conditions
ConditionsYield
With hydrogenchloride
(5-carboxy-pentyl)-dodecyl-dimethyl-ammonium; iodide

(5-carboxy-pentyl)-dodecyl-dimethyl-ammonium; iodide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated HCl
2: Na2CO3; methanol
View Scheme
3-bromo-1-dodecylazacycloheptan-2-one
114919-82-3

3-bromo-1-dodecylazacycloheptan-2-one

Conditions
ConditionsYield
With phosphorus pentachloride; bromine In dichloromethane; chloroform
uranyl nirate hexahydrate

uranyl nirate hexahydrate

UO2(NO3)2(CH2(CH2)4CONC12H25)2
147186-51-4

UO2(NO3)2(CH2(CH2)4CONC12H25)2

Conditions
ConditionsYield
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.;

Laurocapram Chemical Properties

IUPAC Name: 1-Dodecylazepan-2-one
Synonyms of Laurocapram (CAS NO.59227-89-3): 1-Dodecylazacycloheptan-2-one ; 1-Dodecylhexahydro-2H-azepin-2-one ; Azone ; Laurocapramum ; N-Lauryl caprolactam ; 2H-Azepin-2-one, 1-dodecylhexahydro- ; 2H-Azepin-2-one, hexahydro-N-lauryl- ; N-Dodecylcaprolactam
CAS NO: 59227-89-3
Molecular Formula: C18H35NO
Molecular Weight: 281.48
Molecular Structure:
EINECS: 261-668-9
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 11
Polar Surface Area: 20.31 Å2
Index of Refraction: 1.465
Molar Refractivity: 87.02 cm3
Molar Volume: 314.3 cm3
Surface Tension: 32.9 dyne/cm
Density: 0.895 g/cm3
Flash Point: 165.2 °C
Enthalpy of Vaporization: 65.64 kJ/mol
Boiling Point: 404.9 °C at 760 mmHg
Vapour Pressure: 9.12E-07 mmHg at 25°C
Appearance: Colorless or yellowish transparent liquid
Solubility: Insoluble in water, and form emulsions with water, soluble in various organic solvents.
SMILES: O=C1N(CCCCCCCCCCCC)CCCCC1
InChI: InChI=1/C18H35NO/c1-2-3-4-5-6-7-8-9-10-13-16-19-17-14-11-12-15-18(19)20/h2-17H2,1H3
InChIKey: AXTGDCSMTYGJND-UHFFFAOYAS
Std. InChI: InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-13-16-19-17-14-11-12-15-18(19)20/h2-17H2,1H3
Std. InChIKey: AXTGDCSMTYGJND-UHFFFAOYSA-N
Product Categories of Laurocapram (CAS NO.59227-89-3): ketone

Laurocapram Uses

 Laurocapram (CAS NO.59227-89-3) is used as the penetration enhancer in cosmetic preparations and personal-care products. Laurocapram is combined as an excipient not an active ingredient. Excipients are added to ensure that the shelf-life of the active ingredients long enough to be active until internal use. Excipients are combined also to support the active ingredients, so that the latter can be easily administered or absorbed in the body.

Laurocapram Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 8gm/kg (8000mg/kg)   Drug Development and Industrial Pharmacy. Vol. 9, Pg. 725, 1983.
mouse LD50 skin 8gm/kg (8000mg/kg)   Drug Development and Industrial Pharmacy. Vol. 9, Pg. 725, 1983.
rat LD50 intraperitoneal 8gm/kg (8000mg/kg)   Drug Development and Industrial Pharmacy. Vol. 9, Pg. 725, 1983.
rat LD50 intravenous 8gm/kg (8000mg/kg)   Drug Development and Industrial Pharmacy. Vol. 9, Pg. 725, 1983.
rat LD50 oral > 5gm/kg (5000mg/kg)   United States Patent Document. Vol. 4882359,
rat LD50 skin 8gm/kg (8000mg/kg)   Drug Development and Industrial Pharmacy. Vol. 9, Pg. 725, 1983.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   United States Patent Document. Vol. 4882359,
rat LD50 unreported 8gm/kg (8000mg/kg)   Archives of Dermatology. Vol. 118, Pg. 474, 1982.

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