51-98-9 Usage
Chemical Properties
White Solid
Originator
Norlestrin,Parke Davis ,US,1964
Uses
Different sources of media describe the Uses of 51-98-9 differently. You can refer to the following data:
1. Progesteron. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen.
2. Oral contraceptive (in combination with estrogen)
Definition
ChEBI: A 3-oxo Delta4-steroid that is norethisterone in which the hydroxy group has been converted to its acetate ester.
Manufacturing Process
2.98 grams of 17-ethinyl-19-nor-testosterone (norethindrone) are suspended in 30 cc of acetic anhydride and a solution of 1.9 grams of p-toluenesulfonic acid in 19 cc of acetic anhydride is gradually added while cooling and stirring. Complete dissolution takes place after about one hour. After additional 30 to 60 minutes, a thick, pasty mass separates. The reaction is permitted to continue for a total period of 5 hours, whereupon water is added to the reaction mixture and the 3-enol-17-diacetate which separates after stirring for 1 to 2 hours is filtered off, washed until neutral and dried in vacuo over calcium chloride at room temperature.
In order to prepare the monoacetate, the crude diacetate is suspended in 150 cc of methanol and, after adding 1.5 cc, concentrated hydrochloric acid, heated to boiling for 15 minutes in a nitrogen atmosphere. The crude monoacetate which separates upon the addition of water after cooling is filtered off, washed and dried in vacuo over calcium chloride at room temperature. The pure 17-acetete, obtained after repeated recrystallizations from methylene chloride/hexane has a MP of 161° to 162°C.
Brand name
Aygestin (Duramed); Norlutate (Parke-Davis).
Therapeutic Function
Chemical Name: 19-Nor-17α-pregn-4-en-20-yn-3one, 17-hydroxy-, acetate
General Description
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Safety Profile
Suspected carcinogen with experimental tumorigenic data. Human reproductive effects by ingestion and implant routes: menstrual cycle changes, postpartum effects, and changes in fertility. A human teratogen by an unspecified route with developmental abnormalities of the urogenital system. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. Used in the treatment of menstrual dsorders and uterine bleedmg.
Check Digit Verification of cas no
The CAS Registry Mumber 51-98-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 51-98:
(4*5)+(3*1)+(2*9)+(1*8)=49
49 % 10 = 9
So 51-98-9 is a valid CAS Registry Number.
InChI:InChI=1/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18?,19?,20?,21-,22-/m0/s1
51-98-9Relevant articles and documents
An efficient route for the preparation of a 21-fluoro progestin-16 alpha,17 alpha-dioxolane, a high-affinity ligand for PET imaging of the progesterone receptor.
Vijaykumar, Dange,Mao, Wang,Kirschbaum, Karen S,Katzenellenbogen, John A
, p. 4904 - 4910 (2002)
Two different synthetic routes were explored for the synthesis of fluoro furanyl norprogesterone (FFNP) 1, a high-affinity ligand for the progesterone receptor (PgR) that is being developed as a PET imaging agent for PgR-positive breast cancer. Both approaches proceed through a key intermediate, triol 5. The first approach, starting from keto-ketal 2, employed a dioxenyl group as a synthon for installing a corticosteroid side chain in keto-alcohol 4. The second approach, starting from propargylic acetate 12b, involved the application of a two-step method, a Pd(II)-catalyzed oxidative rearrangement followed by a base-catalyzed acetate rearrangement of the intermediate unsaturated acetate 13b, to generate the requisite corticosteroid side chain in keto-acetate 14b. This intermediate was further elaborated to the final product 1 via efficient dihydroxylation with potassium permangnate, furan acetalization with scandium triflate, and mesylation and fluorination reactions. The palladium-catalyzed route is considerably more efficient than the dioxene approach for the synthesis of key intermediate triol 5, and the scandium triflate-catalyzed acetalization, in particular, led to a considerable improvement in the overall yield of the endo furan acetal alcohol 16a. This route provides a major improvement in the overall yield of the final progestin target, FFNP 1.
Preparation method of norethindrone acetate (by machine translation)
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Paragraph 0008; 0029; 0033, (2020/11/23)
The invention discloses a preparation method of norethindrone acetate and belongs to the technical field of drug preparation and processing. The method uses 19 - demethyl -4 - androstenedione as a starting raw material, protects, acetylenically, hydrolyses and esterifies 4 steps to prepare the norethindrone acetate. To the preparation method of the norethindrone acetate, the defects of a traditional process are overcome, reaction conditions are mild, impurities are reduced, overall conversion rate is high, operation is simple and convenient, and the method is suitable for industrial production and has a wide market prospect. (by machine translation)
Using benzotriazole esters as a strategy in the esterification of tertiary alcohols
Morales-Serna, Jose Antonio,Vera, Aline,Paleo, Ehecatl,Garcia-Rios, Erendira,Gavino, Ruben,Garcia De La Mora, Gustavo,Cardenas, Jorge
experimental part, p. 4261 - 4267 (2011/02/25)
Benzotriazole esters formed in situ were found to be efficient intermediates in the esterification of tertiary alcohols using 4-(dimethylamino)pyridine (DMAP) as the base. These mild and basic reaction conditions allow the conversion of various substrates into esters in good yield
