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D4875

Sigma-Aldrich

16-Dehydropregnenolone acetate

≥95%

Sinónimos:

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

Fórmula empírica (notación de Hill):
C23H32O3
Número de CAS:
979-02-2
Peso molecular:
356.50
EC Number:
213-558-7
MDL number:
MFCD00051130
UNSPSC Code:
12352202
PubChem Substance ID:
24893901
NACRES:
NA.77

assay

≥95%

form

powder

SMILES string

CC(=O)OC1CCC2(C)C3CCC4(C)C(CC=C4C(C)=O)C3CC=C2C1

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

InChI key

MZWRIOUCMXPLKV-UHFFFAOYSA-N

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Biochem/physiol Actions

16-Dehydropregnenolone acetate (DPA) is synthesized from steroids sapogenin, diosgenin and solasodine. 16-Dehydropregnenolone acetate (DPA) is a crucial intermediate for the synthesis of steroid hormones-based drugs. It is an antagonist for farnesoid X receptor (FXR) and modulates cholesterol metabolism. It is considered as a potential antihyperlipidemic agent. Chemically synthesized steroid derivatives from DPA have cytotoxic features and could serve as potential anticancer agents.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Facile green synthesis of 16-dehydropregnenolone acetate (16-DPA) from diosgenin
Baruah D, et al.
Synthetic Communications, 46(1), 79-84 (2016)
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
The synthesis of 16-dehydropregnenolone acetate (DPA) from potato glycoalkaloids
Vronena PJE, et al.
ARKIVOC (Gainesville, FL, United States), 2(1), 24-50 (2004)
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)
S B Mahato et al.
The Biochemical journal, 255(3), 769-774 (1988-11-01)
Metabolic processes involving side-chain and ring cleavage of progesterone, 17-hydroxyprogesterone, 11-deoxycortisol and 16-dehydropregnenolone by Arthrobacter simplex were studied. The formation of the metabolites from progesterone indicates a pathway somewhat different from normal in the enzymic reaction sequence, and the 17-hydroxyprogesterone
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