432-60-0

Basic information

• Product Name: Allylestrenol
• Synonyms: 17-allyl-estr-4-en-17-beta-o;17-allylestr-4-en-17-beta-ol;17-alpha-allyl-17-beta-hydroxy-4-estrene;17-alpha-allyl-17-beta-hydroxy-delta(sup4)-estren;17-alpha-allyl-3-deoxy-19-nortestosterone;17-alpha-allyl-4-estren-17-beta-ol;17-alpha-allyl-4-oestrene-17-beta-ol;17-alpha-allylestr-4-en-17-beta-ol
• CAS NO: 432-60-0
• Molecular Formula: C₂₁H₃₂O
• Molecular Weight: 300.48
• EINECS: 207-082-9
• Product Categories: Medicine intermediate;Steroid and Hormone;Inhibitors
• Mol File: 432-60-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 79.5-80°
• Boiling Point: 381.7°C (rough estimate)
• Flash Point: 170.6 °C
• Appearance: Powder
• Density: 0.9914 (rough estimate)
• Vapor Pressure: 2.92E-08mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.95±0.40(Predicted)
• Merck: 14,291
• CAS DataBase Reference: Allylestrenol(CAS DataBase Reference)
• NIST Chemistry Reference: Allylestrenol(432-60-0)
• EPA Substance Registry System: Allylestrenol(432-60-0)

Safety Data

• RTECS: KG7960000
• Hazardous Substances Data: 432-60-0(Hazardous Substances Data)

Usage

Description

Allylestrenol is a synthetic steroid with progestational activity, which means it mimics the effects of the natural hormone progesterone in the body. It is specifically designed to support and maintain the health of the female reproductive system.

Uses

Used in Pharmaceutical Industry:
Allylestrenol is used as a progestational agent for the treatment and support of endangered pregnancies. It helps in maintaining the necessary hormonal balance and ensuring the proper development of the fetus.
Used in Reproductive Health:
Allylestrenol is used as a synthetic sexual steroid for the management of various reproductive health issues, particularly those related to hormonal imbalances. Its progestational activity aids in regulating the menstrual cycle and addressing other related concerns.

Originator

Alilestrenol ,Terapia

Manufacturing Process

To 145 ml of dry methylamine which is cooled to -20°C 1.5 g of lithium cut to small pieces are added. To the solution which is blue in color after 10-20 min, a solution of 3.0 g of oestradiol-3-methylether in 145 ml of absolute ether is added drop wise. Subsequently the reaction mixture is stirred at -10°C for 40 h, after which 50 ml of absolute ethanol are added. Then the methylamine is distilled off at law pressure. To the remaining solution 50 ml of ether and 50 ml of water are added. The water layer is separated and extracted with ether. The ethereal layer is washed with a 2 N hydrochloric acid solution, subsequently with a saturated sodium bicarbonate solution, and then with water. The ethereal solution is dried and evaporated to dryness. The resulting crude reaction product is dissolved in a mixture of benzene and petroleum ether (1:3) and chromatographed over aluminium oxide. The δ4-17β-hydroxy-oestrene obtained after chromatographic purification has a melting point of 80°-90°C and 95°-100°C after repeated crystallization from petroleum ether. A solution of 13.2 g of chromium trioxide in a mixture of 120 ml of water and 20 ml of acetic acid is added, with stirring, to a solution of 20 g of δ4-17β- hydroxy-oestrene in 400 ml of benzene. Subsequently the reaction mixture is vigorously stirred at room temperature for 16 h, after which the benzene layer is separated. The remaining aqueous layer is extracted a few times with benzene and the benzene extracts collected are then added to the separated benzene layer. The benzene extracts are successively washed with dilute sulfuric acid and water and then evaporated to dryness. The residue is crystallized from acetone, and the δ4-17β-oxo-oestrene, melting point 114°-116°C is obtained. To a mixture of 22.4 ml of absolute ether and 1.84 g of magnesium, a mixture of 2.72 ml of allyl bromide and 2.72 ml of absolute ether is added in nitrogen atmosphere. Subsequently a solution of 2 g of δ4-17β-oxo-oestrene in 30 ml of absolute ether is added to this reaction mixture, after which the whole is stirred for 4 h. Then the reaction mixture is poured into acidified ice water. The aqueous mixture is extracted with ether; the ether layer is separated, washed with water, dried over sodium sulfate and evaporated to dryness. The residue is recrystallized from a mixture of ether and petroleum ether, giving δ4-17β-hydroxy-17α-allyl-oestrene, melting point 79.5°-80°C.

Therapeutic Function

Progestin; Antiandrogen

InChI:InChI=1/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1

Synthetic route

allyllithium (3052-45-7) + estr-4-en-17-one → allylestrenol (432-60-0)

estr-4-en-17-one + allyl magnesium halide → allylestrenol (432-60-0)

1,2-Dichloroethylene (540-59-0) + allylestrenol (432-60-0) → (8R,9S,10R,13S,14S,17R)-17-((Z)-3-chloroallyl)-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol

Conditions	Yield
Stage #1: 1,2-Dichloroethylene; allylestrenol With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 22℃; for 0.25h; Glovebox; Inert atmosphere; Stage #2: With C52H57F5MoN2O In benzene at 22℃; for 4h; Glovebox; Inert atmosphere; Stage #3: With silica gel In hexane; ethyl acetate stereoselective reaction;	61%

triethylsilane (617-86-7) + allylestrenol (432-60-0) → C27H46OSi

Conditions	Yield
With dimanganese decacarbonyl; N,N-bis(diphenylphosphino)isopropylamine at 160℃; for 24h; Sealed tube; regioselective reaction;	47%

allylestrenol (432-60-0) → 19,21,24-trinor-17βH-chol-4-en-17-ol (95001-26-6)

Conditions	Yield
Hydrogenation;

allylestrenol (432-60-0) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C27H43BO3

Conditions	Yield
With 1,2-Dichloroethylene at 22℃; for 0.25h; Glovebox; Inert atmosphere;

Upstream product

• 3052-45-7 allyllithium