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D4875

Sigma-Aldrich

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:
979-02-2
Molecular Weight:
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 Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The synthesis of 16-dehydropregnenolone acetate (DPA) from potato glycoalkaloids
Vronena PJE, et al.
ARKIVOC (Gainesville, FL, United States), 2(1), 24-50 (2004)
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
Víctor Pérez-Ornelas et al.
Steroids, 70(3), 217-224 (2005-03-15)
The enzyme 5alpha-reductase is responsible for the conversion of testosterone (T) to its more potent androgen dihydrotestosterone (DHT). This steroid had been implicated in androgen-dependent diseases such as: benign prostatic hyperplasia, prostate cancer, acne and androgenic alopecia. The inhibition of
16-Dehydropregnenolone lowers serum cholesterol by up-regulation of CYP7A1 in hyperlipidemic male hamsters
Ramakrishna R, et al.
The Journal of Steroid Biochemistry and Molecular Biology, 168(1), 110-117 (2017)
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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