ChemicalBook >  Product Catalog >  API >  Hormones and the Endocrine System >  Estrogen and progestin drugs >  17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether

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

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

Product Name:
17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether
CAS:
72-33-3
MF:
C21H26O2
MW:
310.43
EINECS:
200-777-8
Mol File:
72-33-3.mol
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17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether Chemical Properties

Melting point:
153-155 °C(lit.)
alpha 
+2~+8°(D/20℃)(c=1, 1,4-dioxane)
Boiling point:
390.58°C (rough estimate)
Density 
1.0865 (rough estimate)
refractive index 
1.4900 (estimate)
storage temp. 
-20°C Freezer
form 
neat
pka
13.10±0.40(Predicted)
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)
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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

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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

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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17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl etherSupplierMore

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