D4875
16-Dehydropregnenolone acetate
≥95%
Synonym(s):
3β-Acetoxy-5,16-pregnadien-20-one, 3β-Hydroxy-5,16-pregnadien-20-one acetate, 5,16-Pregnadien-3β-ol-20-one acetate
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About This Item
Empirical Formula (Hill Notation):
C23H32O3
CAS Number:
Molecular Weight:
356.50
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
213-558-7
MDL number:
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InChI key
MZWRIOUCMXPLKV-UHFFFAOYSA-N
InChI
1S/C23H32O3/c1-14(24)19-7-8-20-18-6-5-16-13-17(26-15(2)25)9-11-22(16,3)21(18)10-12-23(19,20)4/h5,7,17-18,20-21H,6,8-13H2,1-4H3
SMILES string
CC(=O)OC1CCC2(C)C3CCC4(C)C(CC=C4C(C)=O)C3CC=C2C1
assay
≥95%
form
powder
Quality Level
Biochem/physiol Actions
16-Dehydropregnenolone acetate (DPA) is synthesized from steroids sapogenin, diosgenin and solasodine.[1][2] 16-Dehydropregnenolone acetate (DPA) is a crucial intermediate for the synthesis of steroid hormones-based drugs.[3] It is an antagonist for farnesoid X receptor (FXR) and modulates cholesterol metabolism. It is considered as a potential antihyperlipidemic agent.[4] Chemically synthesized steroid derivatives from DPA have cytotoxic features and could serve as potential anticancer agents.[5]
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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A one-pot efficient process for 16-dehydropregnenolone acetate
Goswami A, et al.
Organic Process Research & Development, 7(3), 306-308 (2003)
A V Kamernitskiĭ et al.
Bioorganicheskaia khimiia, 33(3), 337-341 (2007-08-09)
Acetates of 3beta-hydroxy-3'-methyl-1'(N)-acylandrost-5-eno[16,17-d]pyrazolines bearing monothiooxamide acyl groups were synthesized during the study of approaches to the synthesis of 3'-methylandrosteno[16,17-d]azoles, promising biologically active analogues of 20-keto pregnenanes, and their properties were investigated. The cyclization of delta16-20-thiooxamidohydrazones to the corresponding heterocycles was
Synthesis and activity of novel 16-dehydropregnenolone acetate derivatives as inhibitors of type 1 5alpha-reductase and on cancer cell line SK-LU-1
Silva-Ortiz AV, et al.
Bioorganic & Medicinal Chemistry, 23(24), 7535-7542 (2015)
A V Kamernitzky et al.
Journal of steroid biochemistry, 16(1), 61-67 (1982-01-01)
A new class of modified progesterones with an additional ring in the 16 alpha , 17 alpha-position (pregna-D'-pentaranes) are described. Compounds containing 4- and 6-membered D'-ring (D'4- and D'6-pentaranes) were synthesized by the cycloaddition of acetylene or 1,3-butadiene, respectively, to
Facile green synthesis of 16-dehydropregnenolone acetate (16-DPA) from diosgenin
Baruah D, et al.
Synthetic Communications, 46(1), 79-84 (2016)
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