| Identification | Back Directory | [Name]
3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate | [CAS]
37413-91-5 | [Synonyms]
37413-91-5
16-tetraen-21-yl
Tetraene acetate[3TR]
Prednisone Impurity 12
Acetate tetraene Matter
Tetraen-acetic acid complex
Pregna-1,4,9(11),16-tetraen
21-Hydroxy-1,4,9(11)-tetraene 21-acetate
21-Acetoxypregna-1,4,9(11),16-tetrene-3,20-dione
21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione
3,20-Dioxopregna-1,4,9(11),16-tetrene-21-ol acetate
3,20-dioxopregna-1,4,9(11),16-tetraen-21-yl acetate
21-(Acetyloxy)-pregna-1,4,9(11),16-tetraene-3,20-dione
Pregna-1,4,9(11),16-tetraene-3,20-dione,21-(acetyloxy)-
Pregna-1,4,9(11),16-tetraen-21-ol-3,20-dione 21-acetate
21-hydroxypregna-1,4,9(11),16-tetraene-3,20-dione 21-acetate
3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate ISO 9001：2015 REACH
1,4,9(11),16-PREGNATETRAENE-21-OL-3,20-DIONE-21-ACETATE(3TR) CAS#37413-91-5
Prednisolone impurity 8/21-(Acetyloxy)-pregna-1,4,9(11),16-tetraene-3,20-dione
[2-[(8S,10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,12,14,15-hexahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
2-((8S,10S,13S,14S)-10,13-DiMethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate | [EINECS(EC#)]
253-497-3 | [Molecular Formula]
C23H26O4 | [MDL Number]
MFCD07783010 | [MOL File]
37413-91-5.mol | [Molecular Weight]
366.45 |
| Chemical Properties | Back Directory | [Melting point ]
173-175°C | [Boiling point ]
534.6±50.0 °C(Predicted) | [density ]
1.21±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [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 Information | Back Directory | [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 |
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