16-Dehydropregnenolone acetate (16-DPA) is a chemical compound used as an intermediate or synthon in the production of many semisyntheticsteroids. 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.
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.
Pharmacologyedit
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]
Historyedit
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]
^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. S2CID 98360074.
^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.
^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.
^ "13.4.7 The Crystal Structure of Dehydropregnolone Acetate: A Pregnane". Chemistry and Pharmacology of Naturally Occurring Bioactive Compounds. CRC Press. p. 308.
^ abMarker 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.
^ abcHershberg, Emanuel B.; Oliveto, Eugene P. (20 October 1953). "Process for the manufacture of 17-keto steroids".
^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.
^"Russell Marker and the Mexican Steroid Hormone Industry". American Chemical Society. Retrieved June 5, 2012.
December 07, 2023
dehydropregnenolone, acetate, chemical, compound, used, intermediate, synthon, production, many, semisynthetic, steroids, cephalosporins, penicillins, steroids, while, easy, synthesize, convenient, intermediate, which, made, from, other, more, available, mater. 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 NamesIUPAC name 20 Oxopregna 5 16 dien 3b yl acetateSystematic 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 acetateOther names 16 DPA 5 16 Pregnadien 3b ol 20 one acetate 3b Hydroxy 5 16 pregnadien 20 one acetate 3b Acetoxy 5 16 pregnadien 20 oneIdentifiersCAS Number 979 02 2ECHA InfoCard 100 012 326EC Number 213 558 7PubChem CID 92855UNII 832VMW7ZGC YCompTox Dashboard EPA DTXSID8057857InChI Key MZWRIOUCMXPLKV VMNVZBNLSA NPropertiesChemical formula C 23H 32O 3Molar mass 356 506 g mol 1Appearance White crystalline powderMelting 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 Contents 1 Upstream sources 2 Downstream products 3 Pharmacology 4 History 5 See also 6 ReferencesUpstream sources edit16 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 editCompounds derived from 16 DPA include Corticosteroids mainly of a C22 pregnane backbone hydrocortisone betamethasone dexamethasone beclometasone fluticasone and prednicarbate 5 Progestogen mainly of a C22 pregnane backbone pregnenolone progesterone 6 various synthetic derivatives such as medroxyprogesterone acetate and levonorgestrel Androgens mainly of a C19 androstane 17 keto backbone testosterone 7 and esters various synthetic derivatives Estrogens mainly of a C18 estrane 17 hydroxy backbone estradiol 7 and esters such as estradiol cypionate various synthetic derivatives such as ethinylestradiol 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 editThere 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 editProduction 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 editMexican barbasco tradeReferences edit 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 S2CID 98360074 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 amp Development 7 3 306 308 doi 10 1021 op0200625 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 13 4 7 The Crystal Structure of Dehydropregnolone Acetate A Pregnane Chemistry and Pharmacology of Naturally Occurring Bioactive Compounds CRC Press p 308 a b 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 a b c Hershberg Emanuel B Oliveto Eugene P 20 October 1953 Process for the manufacture of 17 keto steroids 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 Russell Marker and the Mexican Steroid Hormone Industry American Chemical Society Retrieved June 5 2012 Retrieved from https en wikipedia org w index php title 16 Dehydropregnenolone acetate amp oldid 1160962627, wikipedia, wiki, book, books, library,
