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Merck

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:
Assay:
≥95%
Form:
powder
Quality level:
Technical Service
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Quality Level

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

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

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 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)



Global Trade Item Number

SKUGTIN
D4875-10G04061833585764