MOTRETINIDE
- CAS No.
- 56281-36-8
- Chemical Name:
- MOTRETINIDE
- Synonyms
- Tasmaderm;MOTRETINIDE;N-Ethyl-9-[4-methoxy-2,3,6-trimethylphenyl]-3,7-dimethyl-2,4,6,8-nonatetraenamide;(2E,4E,6E,8E)-N-Ethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetrenamide;2,4,6,8-Nonatetraenamide, N-ethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, (2E,4E,6E,8E)-
- CBNumber:
- CB1842555
- Molecular Formula:
- C23H31NO2
- Molecular Weight:
- 353.5
- MDL Number:
- MFCD00867633
- MOL File:
- 56281-36-8.mol
Melting point | 179-180° |
---|---|
FDA UNII | W786807KL1 |
ATC code | D10AD05 |
MOTRETINIDE Chemical Properties,Uses,Production
Originator
Tasmaderm,Roche,Switz.,1981
Uses
Keratolytic.
Definition
ChEBI: Motretinide is a retinoid.
Manufacturing Process
228 g of 5-(4-methoxy-2,3,6-trimethyl-phenyl)-3-methyl-penta-2,4-diene-1-
triphenylphosphonium bromide are introduced under nitrogen gassing into 910
ml of dimethylformamide and treated with cooling at 5°C to 10°C within 20
minutes with 17.5 g of a suspension of sodium hydride (about 50% by
weight) in mineral oil. The mixture is stirred for 1 hour at about 10°C, then
treated at 5°C to 8°C dropwise with 61.8 g of 3-formylcrotonic acid butyl
ester, heated for 2 hours at 65°C, subsequently introduced into 8 liters of icewater and, after the addition of 300 g of sodium chloride, thoroughly
extracted with a total of 18 liters of hexane. The extract is washed 5 times
with 1 liter of methanol/water (6:4 parts by volume) each time and 2 times
with 1.5 liters of water each time, dried over sodium sulfate and evaporated
under reduced pressure to leave 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-
dimethyl-nona-2,4,6,8-tetraen-1-oic acid butyl ester, MP 80°C to 81°C as the
residue.
125.8 g of 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-
tetraen-1-oic acid butyl ester are introduced into 2,000 ml of absolute ethanol
and treated with a solution of 125.8 g of potassium hydroxide in 195 ml of
water. The mixture is heated to boiling under nitrogen gassing for 30 minutes,
then cooled, introduced into 10 liters of ice-water and, after the addition of
about 240 ml of concentrated hydrochloric acid (pH 2-4), thoroughly extracted
with a total of 9 liters of methylene chloride. The extract is washed with about
6 liters of water to neutrality, dried over calcium chloride and evaporated
under reduced pressure. The residue is taken up in 700 ml of hexane. The
precipitated 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-
tetraen-1-oic acid melts at 228°C to 230°C.
28.6 g of 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-
tetraen-1-oic acid are introduced into 300 ml of benzene and treated under
nitrogen gassing with 12 g of phosphorus trichloride. The benzene is
subsequently distilled off under reduced pressure. The remaining 9-(4-
methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid
chloride is dissolved in 1,200 ml of diethyl ether. The solution is added
dropwise at -33°C into 500 ml of ethylamine and stirred for 3 hours. The
reaction mixture is then diluted with 500 ml of diethyl ether and stirred
without cooling for a further 12 hours, the ammonia evaporating. The residue
is dissolved in 10 liters of methylene chloride. The solution is washed 2 times
with 3 liters of water, dried over sodium sulfate and evaporated under reduced
pressure. The remaining N-ethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-
dimethylnona-2,4,6,8-tetraen-1-oic acid amide melts, after recrystallization
from ethanol, at 179°C to 180°C.
brand name
Tasmaderm (Hoffmann-LaRoche).
Therapeutic Function
Antipsoriatic
MOTRETINIDE Preparation Products And Raw materials
Raw materials
1of2
Preparation Products
MOTRETINIDE Suppliers
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
TargetMol Chemicals Inc. | 4008200310 | marketing@tsbiochem.com | China | 23963 | 58 |
Supplier | Advantage |
---|---|
TargetMol Chemicals Inc. | 58 |
TargetMol Chemicals Inc. | 58 |