Etretinate

Product Name: Etretinate
CAS No.: 54350-48-0
Chemical Name: Etretinate
Synonyms: TIGASON;Tegison;Tigasone;Retinoid;ro10-9359;ETRETINATE;Etretinato;tetraenoate;ethyletrinoate;all-trans-ethylester
CBNumber: CB6214647
Molecular Formula: C23H30O3
Formula Weight: 354.48
MOL File: 54350-48-0.mol

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Etretinate Property

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: Solid
color: Light Yellow to Yellow
Stability:: Light Sensitive
CAS DataBase Reference: 54350-48-0(CAS DataBase Reference)
EPA Substance Registry System: Etretinate (54350-48-0)

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Safety

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)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H335May cause respiratory irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHR2919
Product name: Acitretin Related Compound B
Purity: pharmaceutical secondary standard, certified reference material
Packaging: 100MG
Price: $690
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1011029
Product name: Acitretin Related Compound B
Packaging: 20mg
Price: $1220
Updated: 2024/03/01

TCI Chemical

Product number: E1293
Product name: Etretinate
Purity: >98.0%(HPLC)
Packaging: 50mg
Price: $221
Updated: 2024/03/01

TCI Chemical

Product number: E1293
Product name: Etretinate
Purity: >98.0%(HPLC)
Packaging: 250mg
Price: $663
Updated: 2024/03/01

Cayman Chemical

Product number: 19878
Product name: Etretinate
Purity: ≥98%
Packaging: 10mg
Price: $32
Updated: 2024/03/01

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Etretinate Chemical Properties,Usage,Production

Chemical Properties

Crystalline Solid

Originator

Tigason,Roche,UK,1981

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.

Etretinate Preparation Products And Raw materials

Raw materials

Preparation Products

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Etretinate Suppliers

Americas 1 Canada 1 China 100 Europe 4 Germany 1 India 6 Japan 1 United Kingdom 7 United States 24 Global 145

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View Lastest Price from Etretinate manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: Etretinate 54350-48-0
Price: US $1.10/g
Min. Order: 1g
Purity: 99.0% min
Supply Ability: 100 tons min
Release date: 2021-05-25

Career Henan Chemical Co

Product: Etretinate 54350-48-0
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%-99.9%HPLC
Supply Ability: 100KG
Release date: 2020-02-04

54350-48-0, EtretinateRelated Search:

Chlorodimethylphenylsilane Dimethyl sebacate p-Anisidine Dimethyl sulfoxide Dimethyl ether Dimethyl fumarate ETHANE Anisole p-Anisaldehyde (Trifluoromethoxy)benzene Dimethyl sulfate 4-Methoxyphenylacetone Dimethyl carbonate N,N-Dimethylformamide Dimethyl sulfide Enalapril maleate ALMOTRIPTAN Empagliflozin

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

(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

Acitretin Related Compound B (20 mg) (ethyl (all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate)

Acitretin Related CoMpound B

(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid ethyl ester

(ethyl (all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate)

ethylall-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nona

ethyletrinoate

ro10-9359

tetraenoate

TIGASON

Tegison

(all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid Ethyl Ester

Tigasone

TRIMETHYLMETHOXYPHENYLETHYLRETINOATE

ethyl all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

ETRETINATE

Acitretin ethyl ester

AcitretinEthylEster(ForAcitretin)

Etretinato

Retinoid

(2E,4E,6E,8E)-Ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate

2,4,6,8-Nonatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, ethyl ester, (2E,4E,6E,8E)-

all-trans-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid Ethyl Ester

Etretinate USP/EP/BP

Etretinate (Ro 10-9359)

Acitretin EP Impurity B

Acitretin Ethyl EsterQ: What is Acitretin Ethyl Ester Q: What is the CAS Number of Acitretin Ethyl Ester Q: What is the storage condition of Acitretin Ethyl Ester Q: What are the applications of Acitretin Ethyl Ester

Acitretin Related Compound B (ethyl (all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2, (1011029)

Acitretin Acid Impurity B

Acitretin USP Related Compound B

Acitretin Impurity 7 (Acitretin EP Impurity B)

54350-48-0

C23H30O3

Aromatics Compounds

Aromatics

Intermediates & Fine Chemicals

Pharmaceuticals

API

Retinoids