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.
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| Names | |
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| 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 | |
| Identifiers | |
| ECHA InfoCard | 100.012.326 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| 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 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
References
- 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.
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