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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

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Shanghai Longsheng chemical Co.,Ltd.
Tel
021-58099652-8005 13585536065
Fax
021-58099609
Email
bin.wu@shlschem.com
Country
China
ProdList
9809
Advantage
59
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
meilunui@163.com
Country
China
ProdList
4727
Advantage
58
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
ProdList
9891
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
Advantage
61
TOKYO CHEMICAL INDUSTRY CO., LTD.
Tel
03-36680489
Fax
03-3668-0520
Email
Sales-JP@TCIchemicals.com
Country
Japan
ProdList
28387
Advantage
80
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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:


  • 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