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
Names
IUPAC name
20-Oxopregna-5,16-dien-3β-yl acetate
Systematic IUPAC name
(3aS,3bR,7S,9aR,9bS,11aS)-1-Acetyl-9a,11a-dimethyl-3a,3b,4,6,7,8,9,9a,9b,10,11,11a-dodecahydro-3H-cyclopenta[a]phenanthren-7-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
Identifiers
ECHA InfoCard 100.012.326
EC Number
  • 213-558-7
UNII
  • Key: MZWRIOUCMXPLKV-VMNVZBNLSA-N
Properties
C23H32O3
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 a variety of steroidal sapogenins. Industrially useful sources are diosgenin in mexican yams[1][2] and solasodine from certain nightshades. These two sapogenins can be used in a one-pot synthesis.[3] Solanidine in potato greens, an alkaloid sapogenin, is also a key source material.[4]

Downstream products

Compounds derived from 16-DPA include:

Those marked with a * appear on the WHO Model List of Essential Medicines, some as part of a compound medication. The list is by no means complete due to the central role of 16-DPA in steroid production.

Pharmacology

There are no current medical uses of 16-DPA. Studies in male hamsters show that the related chemical 16-DHP acts as an farnesoid X receptor (FXR) antagonist, consequently up-regulating CYP7A1 and lowering serum cholesterol. The CSIR-CDRI holds a patent over 16-DHP for prospective lipid-lowering use.[8]

History

Production of substantial quantities of steroids was not achieved until the Marker degradation in the late 1930s, a synthesis route converting diosgenin into the related compound 16-dehydropregnenolone (16-DP or 16-DHP). This reaction established Mexico as a world center of steroid production.[9] 16-DPA was produced in a variant of Marker degradation published in 1940.[6]

The earliest PubChem patent record for 16-DPA is US2656364A of 1951, describing its conversion into 17-ketosteroids.[7]

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. S2CID 98360074.
  3. Goswami, Amrit; Kotoky, Rumi; Rastogi, Romesh C.; Ghosh, Anil C. (1 May 2003). "A One-Pot Efficient Process for 16-Dehydropregnenolone Acetate" (PDF). Organic Process Research & Development. 7 (3): 306–308. doi:10.1021/op0200625.
  4. Vronen, Patrick J.E.; Koval, Nadeshda; de Groot, Aede (2003). "The synthesis of 16-dehydropregnenolone acetate (DPA) from potato glycoalkaloids". Arkivoc. 2004 (2): 24–50. doi:10.3998/ark.5550190.0005.203.
  5. "13.4.7 The Crystal Structure of Dehydropregnolone Acetate: A Pregnane". Chemistry and Pharmacology of Naturally Occurring Bioactive Compounds. CRC Press. p. 308.
  6. Marker RE, Krueger J (1940). "Sterols. CXII. Sapogenins. XLI. The Preparation of Trillin and its Conversion to Progesterone". J. Am. Chem. Soc. 62 (12): 3349–3350. doi:10.1021/ja01869a023.
  7. Hershberg, Emanuel B.; Oliveto, Eugene P. (20 October 1953). "Process for the manufacture of 17-keto steroids".
  8. Ramakrishna, Rachumallu; Kumar, Durgesh; Bhateria, Manisha; Gaikwad, Anil Nilkanth; Bhatta, Rabi Sankar (1 April 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. PMID 28232149. S2CID 30520080.
  9. "Russell Marker and the Mexican Steroid Hormone Industry". American Chemical Society. Retrieved June 5, 2012.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.