ChemicalBook--->CAS DataBase List--->54350-48-0

54350-48-0

54350-48-0 Structure

54350-48-0 Structure
IdentificationMore
[Name]

Etretinate
[CAS]

54350-48-0
[Synonyms]

ethyl all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate
ETRETINATE
TIGASON
2,4,6,8-nonanetetraenoicacid,9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl
3,7-dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonanetetraenoicaci
all-trans-ethylester
ethylall-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nona
ethyletrinoate
ro10-9359
tetraenoate
Tegison
Acitretin ethyl ester
AcitretinEthylEster(ForAcitretin)
(all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid Ethyl Ester
Tigasone
TRIMETHYLMETHOXYPHENYLETHYLRETINOATE
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonanetetraenoic acid ethyl ester
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid ethyl
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid ethyl ester
[EINECS(EC#)]

259-119-3
[Molecular Formula]

C23H30O3
[MDL Number]

MFCD00866624
[Molecular Weight]

354.48
[MOL File]

54350-48-0.mol
Chemical PropertiesBack Directory
[Appearance]

Crystalline Solid
[Melting point ]

104-1050C
[Boiling point ]

447.69°C (rough estimate)
[density ]

1.0304 (rough estimate)
[refractive index ]

1.5480 (estimate)
[storage temp. ]

Sealed in dry,2-8°C
[solubility ]

Chloroform (Slightly), DMSO (Slightly, Sonicated), Ethyl Acetate (Slightly)
[form ]

neat
[color ]

Light Yellow to Yellow
[Usage]

Aromatic analog of Retinoic Acid. Immunomodulator. Antipsoriatic
[Stability:]

Light Sensitive
[CAS DataBase Reference]

54350-48-0(CAS DataBase Reference)
[EPA Substance Registry System]

54350-48-0(EPA Substance)
Safety DataBack Directory
[HS Code ]

2918992090
[Hazardous Substances Data]

54350-48-0(Hazardous Substances Data)
[Toxicity]

LD50 in mice (1 day): >4000 mg/kg i.p. (Bollag); LD50 (20 day) in mice, rats (mg/kg): 1176, >2000 i.p.; >2000, >4000 orally (Kamm)
Hazard InformationBack Directory
[Chemical Properties]

Crystalline Solid
[Originator]

Tigason,Roche,UK,1981
[Uses]

Aromatic analog of Retinoic Acid. Immunomodulator. Antipsoriatic
[Uses]

Aromatic analog of Retinoic Acid. Immunomodulator. Antipsoriatic.
[Definition]

ChEBI: Etretinate is a retinoid, an enoate ester and an ethyl ester. It has a role as a keratolytic drug.
[Manufacturing Process]

228 g of 5-(4-methoxy-2,3,6-trimethylphenyl)-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, heating for 2 hours at 65°C, subsequently introduced into 8 liters of ice water, 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 liter of water each time, dried over sodium sulfate and evaporated under reduced pressure to leave 9-(4-methoxy-2,3,6-trimethylphenyl)-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-trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8- tetraen-1-oic acid butyl ester are introduced into 2,000 ml of abs. 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-trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8- tetraen-1-oic acid melts at 228°C to 230°C.
60 g of 9-(4-methoxy -2,3,6-trimethylphenyl )-3,7-dimethyl-nona-2,4,6 8- tetraen-1-oic acid are dissolved in 1,000 ml of acetone. After the addition of 128 g of ethyl iodide and 128 g of potassium carbonate, the solution is stirred under nitrogen gassing for 16 hours at 55°C to 60°C and subsequently
evaporated under reduced pressure. The residue is dissolved in 1,300 ml of petroleum ether (BP 80°C to 105°C). The 9-(4-methoxy-2,3,6- trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid ethyl ester crystallizing out at -20°C, melts at 104°C to 105°C.
[Brand name]

Tegison (Roche);Ro 10-9359;Tigasan.
[Therapeutic Function]

Antipsoriatic, Antitumor
[World Health Organization (WHO)]

Etretinate, a retinol derivative, was introduced in 1981 for the treatment of psoriasis. Its use in pregnant women has resulted in major foetal abnormalities. The manufacturer's information emphasizes that the drug is teratogenic and must not be given to women who are pregnant, and that contraceptive measures must be maintained for at least two years after discontinuation of treatment. In some countries, blood banks are advised not to accept as donors persons who have taken etretinate within the previous year.
Spectrum DetailBack Directory
[Spectrum Detail]

Etretinate(54350-48-0)1HNMR
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