CAS 566-65-4

5α-Dihydroprogesterone

Description:

5α-Dihydroprogesterone, also known as 5α-dihydroprogesterone or 5α-DHP, is a steroid hormone derived from progesterone. It is characterized by its structural modifications that include the reduction of the double bond between the C4 and C5 positions of the steroid nucleus, resulting in a saturated A-ring. This compound is biologically active and plays a role in various physiological processes, including the regulation of reproductive functions and the menstrual cycle. It exhibits progestogenic activity, meaning it can bind to progesterone receptors and influence gene expression related to reproductive health. 5α-Dihydroprogesterone is also involved in the metabolism of other steroid hormones and can be synthesized in the body from progesterone through the action of the enzyme 5α-reductase. In terms of physical properties, it is typically a white crystalline solid, and its solubility varies depending on the solvent. Due to its hormonal activity, it is of interest in both clinical and research settings, particularly in the fields of endocrinology and reproductive medicine.

Formula: C₂₁H₃₂O₂

InChI: InChI=1/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

InChI key: InChIKey=XMRPGKVKISIQBV-BJMCWZGWSA-N

SMILES: C[C@@]12[C@@]3([C@]([C@]4([C@](C)(CC3)[C@@H](C(C)=O)CC4)[H])(CC[C@]1(CC(=O)CC2)[H])[H])[H]

Synonyms:

• (+)-(5α)-Pregnane-3,20-dione
• 3,20-Allopregnanedione
• 3,20-Dioxo-5α-pregnane
• 5-Alpha-Dihydroprogesterone
• 5-Alpha-Pregnane-3,20-Dione
• 5-Α-Pregnane-3,20-Dione
• 5-Α-Pregnano-3,20-Diona
• 5-α-Pregnan-3,20-dion
• 5A-pregnane-3-20-dione-allo
• 5α-Dihydro-P4
• 5α-Dihydroprogesterone
• 5α-Pregnanedione
• Nsc 18319
• Pregnan-3,20-dione
• Pregnane-3,20-dione, (5α)-
• ALLOPREGNAN-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
• 5ALPHA-DIHYDROPROGESTERONE
• 5A-PREGNAN-3,20-DIONE
• 5alpha-Pregnane-3,20-dione
• 5-ALPHA-PREGNAN-3,20-DIONE
• ALLOPREGNANDIONE
• ALLOPREGNANE-3,20-DIONE
• 5alpha-Pregnan-3,20-dione-1,2,4,5,6,7-D6
• 3,20-Dioxo-5alpha-pregnane
• 5ALPHA-PREGNANE-3,20-DIONE (ALLO)
• (5-alpha)-pregnane-20-dione
• Pregnane-3,20-dione
• 5-beta-pregnane-3,20-dione

5α-Pregnane-3,20-dione

CAS: 566-65-4

Formula: C₂₁H₃₂O₂

Purity: >98.0%(GC)

Color and Shape: White to Light yellow powder to crystal

Molecular weight: 316.49

Ref: 3B-P2423

Progesterone Impurity 13

CAS: 566-65-4

Formula: C₂₇H₃₈O₃

Color and Shape: White To Off-White Solid

Molecular weight: 410.60

Ref: 4Z-P-3262

5-α-Dihydro Progesterone

CAS: 566-65-4

Formula: C₂₁H₃₂O₂

Color and Shape: White To Off-White Solid

Molecular weight: 316.49

Ref: 4Z-P-326

5a-Pregnane-3,20-dione

CAS: 566-65-4

5a-Pregnane-3,20-dione

Purity: ≥95%

Molecular weight: 316.48g/mol

Ref: 54-BUP16604

5α-Pregnan-3,20-dione-2,2,4,4,17α,21,21,21-d8

CAS: 566-65-4

Purity: 97 atom % D

Color and Shape: White Solid

Molecular weight: 324.53

Ref: 3U-D5799

5a-Pregnane-3,20-dione

CAS: 566-65-4

5a-Pregnane-3,20-dione is a biologically active 5-alpha-reduced metabolite of plasma progesterone

Formula: C₂₁H₃₂O₂

Purity: 99.88% - 99.97%

Color and Shape: Solid

Molecular weight: 316.48

Ref: TM-T5556

5-α-Dihydro Progesterone-d8

CAS: 566-65-4

Formula: C₂₁H₂₄O₂D₈

Molecular weight: 324.54

Ref: 4Z-P-3234

(5a)-Pregnane-3,20-dione

CAS: 566-65-4

Applications (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.
References Caruso, D. et al.: J. Neuroendocrinol., 24, 851 (2012);

Formula: C₂₁H₃₂O₂

Color and Shape: Off-White

Molecular weight: 316.48

Ref: TR-P705150

5α-Pregnane-3,20-dione

Controlled Product

CAS: 566-65-4

5alpha-Pregnane-3,20-dione is a naturally occurring sex steroid hormone. It is produced by the ovaries and testes in humans and other mammals, as well as by the adrenal glands in small amounts. 5alpha-Pregnane-3,20-dione has been shown to inhibit the enzyme activity of hepatic microsomes that are responsible for the conversion of progesterone to 17beta-hydroxyprogesterone (17betaOHP). This inhibition is due to its ability to bind to glucocorticoid receptors. 5alpha-Pregnane-3,20-dione also inhibits fatty acid synthesis in liver cells. The drug's antiproliferative effects on ovarian cells are mediated through a number of mechanisms including transcriptional repression of progesterone receptors and estradiol benzoate binding sites on DNA. 5alpha-Pregnane-3,20-dione has been shown to have an optimal

Formula: C₂₁H₃₂O₂

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 316.48 g/mol

Ref: 3D-FP40764

5α-Pregnan-3,20-dione-2,2,4,4,17α,21,21,21-d8

Controlled Product

CAS: 566-65-4

Applications 5alpha-Pregnan-3,20-dione-2,2,4,4,17alpha,21,21,21-d8 is a useful isotopically labeled compound of (5α)-Pregnane-3,20-dione (P705150)

Formula: C₂₁D₈H₂₄O₂

Color and Shape: Neat

Molecular weight: 324.53

Ref: TR-P705151

5α-Pregnane-3,20-dione

CAS: 566-65-4

Formula: C₂₁H₃₂O₂

Molecular weight: 316.48

Ref: ST-EA-CP-P133044