5α-Pregnane-3,20-dione
- CAS No.
- 566-65-4
- Chemical Name:
- 5α-Pregnane-3,20-dione
- Synonyms
- Pregnane-3,20-dione;5α-dihydroprogesterone;5α-Dihydroprogesterone;5α-pregnane-3,20-dione;ALLOPREGNANDIONE;Allopregnanedione;Pregnane-3,20-dlone;Estrone Impurity 23;5A-PREGNAN-3,20-DIONE;5A-DIHYDROPROGESTERONE
- CBNumber:
- CB0377209
- Molecular Formula:
- C21H32O2
- Molecular Weight:
- 316.48
- MDL Number:
- MFCD00067132
- MOL File:
- 566-65-4.mol
| 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) |
| EWG's Food Scores | 1 |
| FDA UNII | 98G4S1OH0Z |
| NIST Chemistry Reference | 3,20-Allopregnanedione(566-65-4) |
SAFETY
Risk and Safety Statements
| 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 |
5α-Pregnane-3,20-dione price More Price(26)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | R197009 | 5-ALPHA-PREGNANE-3,20-DIONE AldrichCPR | 566-65-4 | 1MG | $139 | 2024-03-01 | Buy |
| Sigma-Aldrich | P7754 | 5α-Pregnane-3,20-dione (allo) progesterone metabolite | 566-65-4 | 500mg | $175 | 2024-03-01 | Buy |
| Sigma-Aldrich | P7754 | 5α-Pregnane-3,20-dione (allo) progesterone metabolite | 566-65-4 | 1g | $313 | 2024-03-01 | Buy |
| TCI Chemical | P2423 | 5α-Pregnane-3,20-dione | 566-65-4 | 1G | $62 | 2024-03-01 | Buy |
| TCI Chemical | P2423 | 5α-Pregnane-3,20-dione | 566-65-4 | 5G | $305 | 2024-03-01 | Buy |
5α-Pregnane-3,20-dione Chemical Properties,Uses,Production
Description
5α-Dihydroprogesterone (5α-DHP), also known as 5α-Pregnane-3,20-dione, is an endogenous progestogen and neurosteroid that is synthesized from progesterone. It is also an intermediate in the synthesis of allopregnanolone and isopregnanolone from progesterone. It is one of the mainly metabolites of progesterone in the digestive gland, the other tentatively identified as3β-hydroxy-5α-pregnan-20-one[1].
In vitro
5a-Pregnane-3,20-dione decreases cell-substrate attachment, adhesion plaques, vinculin expression, and polymerizes F-actin in MCF-7 breast cancer cells.
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: 5alpha-pregnane-3,20-dione is a C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone. It has a role as a human metabolite and a progestogen. It is a 20-oxo steroid, a C21-steroid hormone and a 3-oxo-5alpha-steroid. It is functionally related to a progesterone. It derives from a hydride of a 5alpha-pregnane.
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].
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.
5α-Pregnane-3,20-dione Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Pharmaceuticals Group Corp., Ltd. | +8613004379774 | wu@jiaerke.com | China | 33 | 58 |
| Wuhan Han Sheng New Material Technology Co.，Ltd | +8617798174412 | admin01@hsnm.com.cn | China | 2118 | 58 |
| Nanjing Shizhou Biotechnology Co., Ltd | +86-15850508050 +86-15850508050 | sean.lv@synzest.com | China | 323 | 58 |
| Nantong Guangyuan Chemicl Co,Ltd | +undefined17712220823 | admin@guyunchem.com | China | 616 | 58 |
| Hebei Kangcang new material Technology Co., LTD | +8619133911216 | Jany1001@kangcang.com.cn | China | 338 | 58 |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29797 | 60 |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | info@dakenam.com | China | 15371 | 58 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21695 | 55 |
| career henan chemical co | +86-0371-86658258 | sales@coreychem.com | China | 29914 | 58 |
| Hubei xin bonus chemical co. LTD | 86-13657291602 | linda@hubeijusheng.com | CHINA | 22968 | 58 |
View Lastest Price from 5α-Pregnane-3,20-dione manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-04-19 | ALLOPREGNANDIONE
566-65-4
|
US $200.00-100.00 / g | 1g | 98% | 20 | Hebei Kangcang new material Technology Co., LTD | |
 |
2024-03-08 | 5-alpha-Dihydroprogesterone
566-65-4
|
US $10.00 / kg | 1kg | 99% | 1000kg | Nantong Guangyuan Chemicl Co,Ltd | |
 |
2023-09-14 | 5-alpha-Dihydroprogesterone
566-65-4
|
US $0.00-0.00 / kg | 1kg | 99% | 50tons | Wuhan Han Sheng New Material Technology Co.，Ltd |
-
- ALLOPREGNANDIONE
566-65-4
- US $200.00-100.00 / g
- 98%
- Hebei Kangcang new material Technology Co., LTD
-
- 5-alpha-Dihydroprogesterone
566-65-4
- US $10.00 / kg
- 99%
- Nantong Guangyuan Chemicl Co,Ltd
-
- 5-alpha-Dihydroprogesterone
566-65-4
- US $0.00-0.00 / kg
- 99%
- Wuhan Han Sheng New Material Technology Co.，Ltd