17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether Chemical Properties

Melting point:

153-155 °C(lit.)

Boiling point:

390.58°C (rough estimate)

alpha 

+2～+8°(D/20℃)(c=1, 1,4-dioxane)

Density 

1.0865 (rough estimate)

refractive index 

1.4900 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

Acetonitrile: 1 mg/ml; Ethanol: 1 mg/ml; Methanol: 1 mg/ml

form 

Solid

pka

13.10±0.40(Predicted)

color 

White to off-white

optical activity

[α]15/D +3°, c = 2 in dioxane

Merck 

5917

BRN 

2625905

CAS DataBase Reference

72-33-3(CAS DataBase Reference)

NIST Chemistry Reference

Mestranol(72-33-3)

EPA Substance Registry System

Mestranol (72-33-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-40-48-68

Safety Statements 

22-26-36/37/39-45-36/37

WGK Germany 

3

RTECS 

RC8960000

HS Code 

29372900

Hazardous Substances Data

72-33-3(Hazardous Substances Data)

Toxicity

LD50 oral in rat: > 10gm/kg

MSDS

• Language:English Provider:17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether Usage And Synthesis

Chemical Properties

Crystalline Solid

Originator

Enovid ,Searle ,US ,1957

Uses

Pharmacological estrogen molecule

Uses

Mestranol is an orally active estrogenic steroid. It was the estrogen used in many of the first oral contraceptives

Uses

antiemetic

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.

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