6-Methyleneandrost-4-ene-3,17-dione Chemical Properties

Melting point:

163-165 °C

Boiling point:

450.8±45.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), DMSO (Heated), Methanol (Slightly)

form 

Solid

color 

Pale Yellow to Light Beige

InChI

InChI=1S/C20H26O2/c1-12-10-14-15-4-5-18(22)20(15,3)9-7-16(14)19(2)8-6-13(21)11-17(12)19/h11,14-16H,1,4-10H2,2-3H3/t14-,15-,16-,19+,20-/m0/s1

InChIKey

KQRGETZTRARSMA-DAELLWKTSA-N

SMILES

C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)C(=O)CC3)CC2=C

Safety Information

HS Code 

2914299000

6-Methyleneandrost-4-ene-3,17-dione Usage And Synthesis

Uses

1,2-Dihydro Exemestane is a related compound of Exemestane (E957000).

Synthesis

The general procedure for the synthesis of (8R,9S,10R,13S,14S)-10,13-dimethyl-6-methylene-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione from formaldehyde and androstenedione was as follows: 2.0 g of androst-4-ene-3,17 -dione (0.01 mol) was dissolved in 13 mL of anhydrous THF and 2 mL of ethanol, 2 mL of anhydrous triethyl orthoformate and 26 mg of p-toluenesulfonic acid monohydrate were added. The reaction mixture was stirred at 40 °C for about 1 hour. Subsequently, 50 mg of p-toluenesulfonic acid monohydrate was added and stirring was continued for about 2 hours. After the reaction was completed, cooled to room temperature, 1 mL of N-methylaniline and 1 mL of 40% formaldehyde aqueous solution was added to the reaction flask and the mixture was stirred at 40°C for about 4 hours. After cooling to room temperature again, 10 mL of 37% HCl was added and stirring was continued for 2 hours. The reaction solution was transferred to a partition funnel and extracted with EtOAc. The organic phase was dried with Na2SO4 and purified by silica gel chromatography to afford 0.84 g of 6-methylene-androst-4-ene-3,17-dione (3) as a white solid with >95% chemical purity and a melting point of 159-163 °C.

References

[1] Patent: WO2010/76811, 2010, A2. Location in patent: Page/Page column 9
[2] Steroids, 2013, vol. 78, # 11, p. 1148 - 1151
[3] Patent: CN105622694, 2016, A. Location in patent: Paragraph 0010

6-Methyleneandrost-4-ene-3,17-dione(19457-55-7)Related Product Information

• Androsta-1,4-diene-3,17-dione
• Androstenedione
• Tamoxifen
• Anastrozole
• Exemestane
• 6-HydroxyMethyl ExeMestane
• Exemestane Impurity 1
• NSC44826
• Exemestane Impurity 2
• Epoxy Exemestane (6-Alfa Isomer)
• Epoxy Exemestane (6-Beta Isomer)
• ExeMestane Related CoMpound
• 6-Oxo Boldione
• Exemestane impurity B -F
• Methylene boldenone
• Exemestane EP Impurity C
• Exemestane Impurity 13
• 5β-Androstane-3,6,17-trione