68-23-5 Usage
Chemical Properties
White to Off-White Solid
Originator
Enovid, Searle ,US,1957
Uses
Different sources of media describe the Uses of 68-23-5 differently. You can refer to the following data:
1. Norethynodrel (Norethindrone EP Impurity D) (>90%) is a progestin used in Enovid, an oral contraceptive, also used in the treatment of endometriosis and hypermenorrhea.
2. Norethynodrel is a progestin used in Enovid, an oral contraceptive, also used in the treatment of endometriosis and hypermenorrhea.
Manufacturing Process
Convenient starting materials are the ethers of 3-hydroxy-13-methyl1,4,6,7,8,9,11,12,13,14,16,17-dodecahydro-15H-cyclopenta-α-phenanthren
2474 17-one described in US Patent 2,655,518, according to US Patent 2,691,028 where the following preparation is also described. The methyl ether is also designated as 3-methoxy-17-oxo-2,5-estradieneA stirred solution of 10.6 parts of 3-methoxy-13-methyl-1,4,6,7,8,9,11,12,13, 14,16,17dodecahydro-15H-cyclopenta-α-phenanthren-17-one in 700 parts of anhydrous ether and 45 parts of dry toluene is cooled to 0°C and saturated with dry acetylene. While a slow stream of acetylene is passed through the reaction mixture, a solution of 20 parts of potassium t-amylate in 135 parts of anhydrous t-pentanol is added in the course of 15 minutes with stirring. Passage of acetylene and stirring are continued for an additional 4? hours. After standing at 0°C for 16 hours, the mixture is washed with aqueous ammonium chloride solution until the aqueous phase is neutral, then with water and saturated sodium chloride solution. The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to a residue of about 250 parts. 500 parts of petroleum ether are added and after standing at 0°C for an hour, the mixture is filtered. The collected precipitate is recrystallized from ether. The resulting 3-methoxy-13-methyl-17-ethynyl1,4,6,7,8,9,11,12,13,14,16,17-dodecahydro-15H-cyclopenta-α-phenanthren17-ol melts at about 181° to 182°C.
To a refluxing solution of 10 parts of 3-methoxy-17-ethynyl-17-hydroxy-13methyl-1,4,6,7,8,9,11,12,13,14,16,17-dodecahydro-15H-cyclopenta-αphenanthrene in 500 parts of methanol, 20 parts of glacial acetic acid are added. Refluxing is continued for 7 minutes, water is added to the point of turbidity and the reaction mixture is permitted to come to room temperature. The precipitate is collected on a filter and recrystallized from aqueous methanol. The 13-methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14, 16,17-tetradecahydro-15H-cyclopenta-α-phenanthren-3-one thus obtained melts at about 169° to 170°C.
Therapeutic Function
Progestin
Safety Profile
Suspected carcinogen
with experimental tumorigenic data. Human
and experimental reproductive effects.
Mutation data reported. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 68-23-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 8 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 68-23:
(4*6)+(3*8)+(2*2)+(1*3)=55
55 % 10 = 5
So 68-23-5 is a valid CAS Registry Number.
InChI:InChI=1/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,16-18,22H,4-12H2,2H3/t16?,17?,18?,19-,20-/m0/s1
68-23-5Relevant articles and documents
Water-soluble steroid compounds
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, (2008/06/13)
Beta-cyclodextrin forms a water-soluble complex or inclusion compound with steroid compounds having a molecular structure smaller than the interior cavity in the doughnut-shaped molecular structure of beta-cyclodextrin. The resulting inclusion compounds can be used for a variety of applications including aqueous topical ophthalmic preparations and topical dermatological ointments.
Preparation of 5α,10α epoxysteroids
Ponsold,Schade,Wunderwald
, p. 298 - 306 (2007/10/05)
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