6-Methyl-16-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate

Basic Information

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CAS Number

2919-66-6

Molecular Formula

C25H32O4

Molecular Weight

396.53 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ketones

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Surfactants Anionic Surfactants

Polymers and Plastics Thermoplastics Polyolefins

Basic Physical Properties

Melting Point

202-204 ºC

Boiling Point

440.2°C (rough estimate)

Refractive Index

1.6000 (estimate)

Specific Rotation

D23 -127° (c = 0.31 in chloroform)

SMILES

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CC1=CC2C(CCC3(C2CC(=C)C3(C(=O)C)OC(=O)C)C)C4(C1=CC(=O)CC4)C

InChI

InChI=1S/C25H32O4/c1-14-11-19-20(23(5)9-7-18(28)13-21(14)23)8-10-24(6)22(19)12-15(2)25(24,16(3)26)29-17(4)27/h11,13,19-20,22H,2,7-10,12H2,1,3-6H3/t19-,20+,22+,23-,24+,25+/m1/s1

InChIKey

UDKABVSQKJNZBH-DWNQPYOZSA-N

LogP

4.741400000000005

Topological Polar Surface Area

60.440000000000005 Å²

Hydrogen Bond Donor/Acceptor

0 / 4

Complexity

893

Safety Information

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Toxicity

LD50 (mg/kg): >8000 orally in rats; >2500 i.p. in mice (Zimbelman)

Synonyms & References

English

CHEBI:34831
NS00028653
4W5HDS3936
SCHEMBL4520
17a-Acetoxy-6-methyl-16-methylene-4,6-pregnadiene-3,20-dione
BS-42198
Pregna-4,20-dione, 17-hydroxy-6-methyl-16-methylene-, acetate
AB00918404-04
EINECS 220-859-7
MGA
Melengestrol acetate, VETRANAL(TM), analytical standard
2919-66-6
MGA 100 (steroid)
[(8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate
Pregna-4,6-diene-3,20-dione, 17-hydroxy-6-methyl-16-methylene-, acetate
MGA 100, MGA 200
MGA500
BDH 1921
Melengestrol acetate (USP)
NCGC00166298-02
D04900
Melengestrol acetate [USAN]
Melengestrol acetate, United States Pharmacopeia (USP) Reference Standard
HMS3715D05
MELENGESTROL ACETATE [MI]
NCGC00257329-01
Pregna-4,20-dione, 17-(acetyloxy)-6-methyl-16-methylene-
Melengestrol acetate 100 microg/mL in Acetonitrile
HMS2233N13
MELENGESTROL ACETATE
Pregna-4,6-diene-3,20-dione, 17-(acetyloxy)-6-methyl-16-methylene-

MDL Number

MFCD00072142

FAQ

What are the physical and chemical properties of 6-Methyl-16-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate (CAS: 2919-66-6)?

6-Methyl-16-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate (CAS: 2919-66-6) is a crystalline solid with a molecular formula C22H30O4 and a molecular weight of approximately 358.48 g/mol. It has low solubility in water but is soluble in organic solvents like ethanol and acetone. This compound is relatively stable under normal conditions but reacts with strong bases and acids. It has a melting point around 70-72°C.

How is 6-Methyl-16-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate (CAS: 2919-66-6) typically synthesized?

6-Methyl-16-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate is synthesized through a series of reactions starting from progesterone. The process involves acetylation of a specific intermediate, followed by ring opening and methylation steps. Common catalysts include acid catalysts and transition metal complexes, with high selectivity and a yield of up to 85%.

What industries use 6-Methyl-16-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate (CAS: 2919-66-6)?

6-Methyl-16-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate (CAS: 2919-66-6) is primarily used in the pharmaceutical industry for the synthesis of progestins and other steroid hormones. It is also explored in research for its potential in polymers and sensors due to its unique chemical structure.

What precautions should be taken when handling 6-Methyl-16-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate (CAS: 2919-66-6)?

When handling 6-Methyl-16-methylene-3,20-dioxopregna-4,6-dien-17-yl acetate (CAS: 2919-66-6), use appropriate personal protective equipment (PPE) such as gloves and a lab coat. Store it in a cool, dry place, away from direct sunlight and heat sources. Work in a well-ventilated area or a fume hood. In case of spills, use absorbent material and follow local safety guidelines. Always consult the Safety Data Sheet (SDS) for detailed handling and disposal information.