5α-Pregnane-3,20-dione
Description In vitro- Product Name
- 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;ALLOPREGNAN-3,20-DIONE
- CBNumber
- CB0377209
- Molecular Formula
- C21H32O2
- Formula Weight
- 316.48
- MOL File
- 566-65-4.mol
5α-Pregnane-3,20-dione Property
- 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
- WGK Germany
- 3
- RTECS
- TU4157150
- HS Code
- 2937.29.9095
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H312Harmful in contact with skin
H332Harmful if inhaled
H351Suspected of causing cancer
- Precautionary statements
-
P201Obtain special instructions before use.
P202Do not handle until all safety precautions have been read and understood.
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P281Use personal protective equipment as required.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P308+P313IF exposed or concerned: Get medical advice/attention.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P322Specific measures (see …on this label).
P330Rinse mouth.
P363Wash contaminated clothing before reuse.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- R197009
- Product name
- 5-ALPHA-PREGNANE-3,20-DIONE
- Purity
- AldrichCPR
- Packaging
- 1MG
- Price
- $139
- Updated
- 2024/03/01
- Product number
- P7754
- Product name
- 5α-Pregnane-3,20-dione (allo)
- Purity
- progesterone metabolite
- Packaging
- 500mg
- Price
- $175
- Updated
- 2024/03/01
- Product number
- P7754
- Product name
- 5α-Pregnane-3,20-dione (allo)
- Purity
- progesterone metabolite
- Packaging
- 1g
- Price
- $313
- Updated
- 2024/03/01
- Product number
- P2423
- Product name
- 5α-Pregnane-3,20-dione
- Packaging
- 1G
- Price
- $62
- Updated
- 2024/03/01
- Product number
- P2423
- Product name
- 5α-Pregnane-3,20-dione
- Packaging
- 5G
- Price
- $305
- Updated
- 2024/03/01
5α-Pregnane-3,20-dione Chemical Properties,Usage,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
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View Lastest Price from 5α-Pregnane-3,20-dione manufacturers
- Product
- 5-alpha-Dihydroprogesterone 566-65-4
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 1000kg
- Release date
- 2023-11-02
- Product
- 5-alpha-Dihydroprogesterone 566-65-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 50tons
- Release date
- 2023-08-24
- Product
- Pregnane-3,20-dione 566-65-4
- Price
- US $0.00/g
- Min. Order
- 1g
- Purity
- 99.9%
- Supply Ability
- 200kgs
- Release date
- 2022-10-13