ChemicalBook CAS DataBase List 566-65-4

566-65-4

Name	5-alpha-Dihydroprogesterone
CAS	566-65-4
EINECS(EC#)	209-297-3
Molecular Formula	C21H32O2
MDL Number	MFCD00067132
Molecular Weight	316.48
MOL File	566-65-4.mol

Synonyms

5A-DIHYDROPROGESTERONE 5ALPHA-DIHYDROPROGESTERONE 5-ALPHA-PREGNAN-3,20-DIONE 5ALPHA-PREGNANE-3,20-DIONE (ALLO) 5A-PREGNAN-3,20-DIONE 5 A-PREGNANE-3 20-DIONE (5S,8R,9S,10S,13S,14S,17S)-17-ACETYL-10,13-DIMETHYL-HEXADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE ALLOPREGNAN-3,20-DIONE ALLOPREGNANDIONE ALLOPREGNANE-3,20-DIONE (5-alpha)-pregnane-20-dione 3,20-Allopregnanedione 3,20-Dioxo-5alpha-pregnane 5alpha-Pregnane-3,20-dione 5-beta-pregnane-3,20-dione Pregnane-3,20-dione Pregnane-3,20-dione, (5alpha)- 5A-pregnane-3-20-dione-allo 5alpha-Pregnan-3,20-dione-1,2,4,5,6,7-D6 5α-dihydroprogesterone

Chemical Properties

Melting point	200 °C
Boiling point	429.2±38.0 °C(Predicted)
density	1.048±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
solubility	Chloroform (Slightly), Ethyl Acetate (Slightly)
form	Solid
color	White to Off-White
InChI	InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14?,16-,17+,18-,19-,20-,21+/m0/s1
InChIKey	XMRPGKVKISIQBV-CVHNGYJVSA-N
SMILES	C1(=O)CC2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)[C@@H](C(=O)C)CC3)CC2
CAS DataBase Reference	566-65-4(CAS DataBase Reference)
NIST Chemistry Reference	3,20-Allopregnanedione(566-65-4)

Safety Data

Symbol(GHS)	GHS07,GHS08
Signal word	Warning
Hazard statements	H312-H302-H332-H351-H361fd
Precautionary statements	P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501-P201-P202-P281-P308+P313-P405-P501-P261-P271-P304+P340-P312
WGK Germany	3
RTECS	TU4157150
HS Code	2937.29.9095

Hazard Information

Uses

(5α)-Pregnane-3,20-dione exerts neuroprotective effects in chronic autoimmune encephalomyelitis (EAE). The neuroactivity of the steroid acts as a therapeutic agent for multiple sclerosis.

Definition

ChEBI: A C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone.

Biochem/physiol Actions

(5α)-Pregnane-3,20-dione is a high-level metabolite of progesterone in breast cancer tissue (but not normal breast tissue); promotes cell proliferation and detachment. Receptors appear only on the cell surface of MCF-7 breast cancer cells, not on nuclei where most other steroid receptors are located.

Biological Activity

Digestive gland subcellular fractions readily converted P4 into 5-pregnane-3,20-dione and minor amounts of a second metabolite and then 5-pregnane-3,20-dione was further metabolized to 3-hydroxy-5-pregnane-20-one (3,20-one) by 3β-HSD. This reaction was significantly inhibited by trilostane which is a 3β-HSD inhibitor[1-2].

IC 50

Human Endogenous Metabolite

storage

Store at -20°C

References

[1] Dimastrogiovanni G, et al. Progesterone is actively metabolized to 5-pregnane-3,20-dione and 3-hydroxy-5-pregnan-20-one by the marine mussel Mytilus galloprovincialis. Aquatic Toxicology, 2015; 73-100.
[2] Ankley G, et al. Effects?of?progesterone?on?sperm motility?in?fathead?minnow. Aquatic Toxicology, 2011; 104: 121-125.

Material Safety Data Sheet(MSDS)

Questions And Answer

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