16-Dehydropregnenolone acetate

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-Dehydropregnenolone acetate
IUPAC name
[(3S,8R,9S,10R,13S,14S)-17-Acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Other names
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
ECHA InfoCard 100.012.326
EC Number
  • 213-558-7
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).
Infobox references

Upstream sources

16-DPA can be produced from diosgenin in mexican yams[1][2] or from solanidine in potatoes.[3]

Downstream targets

Compounds derived from 16-DPA include hydrocortisone, betamethasone, dexamethasone, beclometasone, fluticasone, and prednicarbate,[4] the first four of which appear on the WHO Model List of Essential Medicines.

See also


  1. us 5808117, Pritish Kumar Chowdhury, "Process for the production of 16-Dehydropregenolone acetate form diosgenin", issued 15-09-1998
  2. 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.
  3. 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.
  4. "13.4.7 The Crystal Structure of Dehydropregnolone Acetate: A Pregnane". Chemistry and Pharmacology of Naturally Occurring Bioactive Compounds. f CRC Press: 308.
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