72-33-3 Usage
Chemical Properties
Crystalline Solid
Originator
Enovid ,Searle ,US ,1957
Uses
Different sources of media describe the Uses of 72-33-3 differently. You can refer to the following data:
1. Mestranol is an orally active estrogenic steroid. It was the estrogen used in many of the first oral contraceptives
2. Pharmacological estrogen molecule
Definition
ChEBI: A terminal acetylenic compound that is (17alpha)-17-ethynylestra-1(10),2,4-triene substituted by a methoxy group at position 3 and a hydroxy group at position 17.
Manufacturing Process
A stirred solution of 120 parts of 3-methoxy-δ1,3,5-estratrien-17-one in 2,600 parts of anhydrous toluene and 4,300 parts of anhydrous ether is saturated with a slow stream of acetylene. In the course of 30 minutes there is added a solution of 120 parts of potassium tert-amylate in 2,800 parts of anhydrous tert-pentanol. The passage of acetylene and stirring are continued for an additional 5 hours after which the reaction mixture is washed 5 times with 3,000-part portions of saturated ammonium chloride solution and then with water. It is then dried over anhydrous sodium sulfate and concentrated to dryness under vacuum. The residue is recrystallized from methanol. The 3- methoxy-17-ethynyl-δ1,3,5 estratrien-17-ol thus obtained melts at about 143° to 146°C. A further recrystallization from acetone yields crystals melting at about 150° to 151°C.
Therapeutic Function
Estrogen
Safety Profile
Confirmed carcinogen
with experimental. neoplastigenic,
tumorigenic, and teratogenic data.
Moderately toxic by subcutaneous route.
Human reproductive effects by ingestion:
changes in ovaries and fallopian tubes,
ferthty effects. Experimental reproductive
effects. Mutation data reported. An FDA
proprietary drug. A steroid used in oral
contraceptives. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 72-33-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 2 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 72-33:
(4*7)+(3*2)+(2*3)+(1*3)=43
43 % 10 = 3
So 72-33-3 is a valid CAS Registry Number.
InChI:InChI=1/C29H52/c1-7-22(20(2)3)12-11-21(4)25-15-16-26-24-14-13-23-10-8-9-18-28(23,5)27(24)17-19-29(25,26)6/h20-27H,7-19H2,1-6H3/t21-,22-,23+,24+,25-,26+,27+,28+,29-/m1/s1
72-33-3Relevant articles and documents
Microbial transformation of mestranol by Cunninghamella elegans
Choudhary, Muhammad Iqbal,Musharraf, Syed Ghulam,Siddiqui, Zafar Ali,Khan, Naik Tameen,Ali, Rahat Azhar,Atta-ur-Rahman
, p. 1011 - 1013 (2005)
The microbial transformation of an oral contraceptive, mestranol (1) by Cunninghamella elegans yielded two hydroxylated metabolites, 6β-hydroxymestranol (2) and 6β,12β-dihydroxymestranol (3). Metabolite 3 was found to be a new compound. These metabolites were structurally characterized on the basis of spectroscopic techniques.
Fluoride-assisted activation of calcium carbide: A simple method for the ethynylation of aldehydes and ketones
Hosseini, Abolfazl,Seidel, Daniel,Miska, Andreas,Schreiner, Peter R.
supporting information, p. 2808 - 2811 (2015/06/16)
The fluoride-assisted ethynylation of ketones and aldehydes is described using commercially available calcium carbide with typically 5 mol % of TBAF·3H2O as the catalyst in DMSO. Activation of calcium carbide by fluoride is thought to generate an acetylide "ate"-complex that readily adds to carbonyl groups. Aliphatic aldehydes and ketones generally provide high yields, whereas aromatic carbonyls afford propargylic alcohols with moderate to good yields. The use of calcium carbide as a safe acetylide ion source along with economic amounts of TBAF·3H2O make this procedure a cheap and operationally simple method for the preparation of propargylic alcohols.
An improved synthesis of nomegestrol acetate
Lu, He-Lin,Wu, Zong-Wen,Song, Shu-Yong,Liao, Xiao-Dan,Zhu, Yan,Huang, Yun-Sheng
, p. 431 - 436 (2014/04/17)
Oral contraceptives (OCs) are synthetic steroids, or progestins, which are structurally related to testosterone or to progesterone. Many progestins have been synthesized and approved for OCs, hormonal replacement therapy (HRT), or the treatment of some gynecological disorders. Nomegestrol acetate (NOMAc) is a newly approved OC and has gained rapid acceptance in many countries for OC or HRT. The synthesis of NOMAc remains challenging and costly. We have developed a novel and improved procedure for the synthesis of NOMAc with a total of 11 steps and an overall good yield without the use of hazardous reagents.
