3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate

3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate Property

Melting point:

173-175°C

Boiling point:

534.6±50.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO: 100 mg/mL (272.89 mM)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C23H26O4/c1-14(24)27-13-21(26)20-7-6-18-17-5-4-15-12-16(25)8-10-22(15,2)19(17)9-11-23(18,20)3/h7-10,12,17-18H,4-6,11,13H2,1-3H3/t17-,18-,22-,23-/m0/s1

InChIKey

UFEOMHFPJREVTP-PTRHGPIFSA-N

SMILES

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione is an intermediate of delta 9,11 steroids synthesis, for example, Vamorolone?(HY-109017). The delta 9,11 steroids are modifications of glucocorticoids and has anti-inflammatory properties. The delta 9,11 steroids are agents for protection against cell damage (lipid peroxidation) and inhibition of neovascularization[1].

Synthesis

Under nitrogen protection, 50 g (0.13 mol) pregnane-1,4,9(11)-triene-3,20-dione-17-hydroxy-21-acetate was added to a reaction vial with 200 mL of pyridine, cooled to -15 °C and stirred. Subsequently, 30 g of N-chlorosuccinimide (NCS) was added and 17.5 g (0.27 mol) of SO2 gas was slowly vented over a period of 1 h. The reaction temperature was controlled to not exceed -10°C. After completion of the venting, stirring was continued for half an hour. Upon completion of the reaction, the formation of a mixed solution containing δ16 steroidal compound (I) was confirmed by TLC monitoring. This mixed solution was poured into 300 mL of concentrated hydrochloric acid, 2000 mL of ice water was added, and left to stand for 2 hours to remove water-soluble impurities. After separating the aqueous layer, the organic layer was concentrated to get at least the amount of liquid, filtered to get a solid, and dried at 60 °C to obtain 47 g of δ16 steroidal compound (I). The purity of this δ16 steroidal compound (I) was 99% as determined by high performance liquid chromatography (HPLC).

References

[1] Erica K M Reeves, et al. VBP15: preclinical characterization of a novel anti-inflammatory delta 9,11 steroid. Bioorg Med Chem DOI:10.1016/j.bmc.2013.02.009