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ChemicalBook CAS DataBase List 1,4-PREGNADIEN-17,20-BETA, 21-TRIOL-3,11-DIONE
600-92-0

1,4-PREGNADIEN-17,20-BETA, 21-TRIOL-3,11-DIONE synthesis

4synthesis methods
-

Yield:53-03-2 30% ,600-92-0 10%

Reaction Conditions:

with Rhodococcus rhodnii DSM 43960 in dimethyl sulfoxide; for 24 h;Green chemistry;Enzymatic reaction;

Steps:

4.3. Biotransformation of Cortisone 1 with Rhodococcus rhodnii (24 h)

General procedure: A loopful of Rhodococcus rhodnii from a culture on plate count agar (PCA) containingglucose (1 g/L), yeast extract (2.5 g/L), tryptone (5 g/L), and agar (15 g/L) was inoculatedin three 50-mL Erlenmeyer flasks, closed with cotton plugs, in sterile plate count broth(PCB) (20 mL) containing glucose (1 g/L), yeast extract (2.5 g/L), and tryptone (5 g/L)and incubated at 30 °C and 110 rpm in an orbital shaker for 48 h. The whole cultureswere introduced into 500-mL Erlenmeyer flasks containing 200 mL of sterile PCB, andafter 48 h incubation at 30 °C and 110 rpm, cortisone (0.2 g) in DMSO (2 mL) was added,and the culture was maintained in the same conditions for 24 h. All tests were carriedout in triplicate for statistical significance. A blank sample was also incubated containingall the reagents but no bacteria. The reaction was monitored by withdrawing samples(1 mL) every 6 h up to 24 h of reaction and followed by TLC analysis (ethyl acetate as theeluent). After 24 h, the cells were removed by centrifugation (5242 RCF, 20 min), and the supernatant was extracted with ethyl acetate (3 x 200 mL). The organic layer was driedover anhydrous Na2SO4, the solvent evaporated, and the crude mixture purified on achromatographic column (silica gel; ethyl acetate as the eluent). The biotransformationyields were obtained by working out the percentage of the ratio between the moles of theproduct obtained compared to the moles of the administered substrate.

References:

Bertolasi, Valerio;Buzzi, Raissa;Costa, Stefania;Pedrini, Paola;Semeraro, Bruno;Summa, Daniela;Vertuani, Silvia;Zappaterra, Federico [Molecules,2021,vol. 26,# 5,art. no. 1352]