16-Dehydropregnenolone Acetate

16-Dehydropregnenolone Acetate
Names
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
Identifiers
EC Number 213-558-7
Properties
C23H32O3
Molar mass 356.506
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

16-Dehydropregnenolone acetate (16-DPA) is a core structure (synthon) in the production of many semisynthetic steroidal compounds. 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.

Upstream sources

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

Pharmaceutical Use

Bioidentical Pregnenolone only occurs after catalytic hydrogenation, although DP can be issued for use in its own right.[4]

Downstream targets

Compounds derived from 16-DPA include hydrocortisone, betamethasone, dexamethasone, beclometasone, fluticasone, and prednicarbate,[5] the first four of which appear on the WHO Model List of Essential Medicines.

See also

References

  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. ↑ Ramakrishna, Rachumallu; Kumar, Durgesh; Bhateria, Manisha; Gaikwad, Anil Nilkanth; Bhatta, Rabi Sankar (2017). "16-Dehydropregnenolone lowers serum cholesterol by up-regulation of CYP7A1 in hyperlipidemic male hamsters". The Journal of Steroid Biochemistry and Molecular Biology. 168: 110–117. doi:10.1016/j.jsbmb.2017.02.013. ISSN 0960-0760.
  5. ↑ "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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