16-Dehydropregnenolone acetate (16-DPA) is a chemical compound used as an intermediate or synthon in the production of many semisynthetic steroids. As 7-ACA is for cephalosporins and 6-APA is for penicillins, 16-DPA is for steroids. While it is not easy to synthesize, it is a convenient intermediate which can be made from other more available materials, and which can then be modified to produce the desired target compound.
16-DPA; 5,16-Pregnadien-3β-ol-20-one acetate; 3β-Hydroxy-5,16-pregnadien-20-one acetate; 3β-Acetoxy-5,16-pregnadien-20-one
CompTox Dashboard (EPA)
|Molar mass||356.506 g·mol−1|
|Appearance||White crystalline powder|
|Melting point||171–172 °C (340–342 °F; 444–445 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Compounds derived from 16-DPA include hydrocortisone, betamethasone, dexamethasone, beclometasone, fluticasone, and prednicarbate, the first four of which appear on the WHO Model List of Essential Medicines.
- us 5808117, Pritish Kumar Chowdhury, "Process for the production of 16-Dehydropregenolone acetate form diosgenin", issued 15-09-1998
- Baruah, Diganta; Das, Ram Nath; Konwar, Dilip (2015). "Facile green synthesis of 16-dehydropregnenolone acetate (16-DPA) from diosgenin,". Synthetic Communications. 46 (1): 79–84. doi:10.1080/00397911.2015.1121280.
- Vronen, Patrick J.E.; Koval, Nadeshda; de Groot, Aede. "The synthesis of 16-dehydropregnenolone acetate (DPA) from potato glycoalkaloids". Arc. Org. Chem. 2004 (2): 24–50. doi:10.3998/ark.5550190.0005.203.
- "13.4.7 The Crystal Structure of Dehydropregnolone Acetate: A Pregnane". Chemistry and Pharmacology of Naturally Occurring Bioactive Compounds. f CRC Press: 308.