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P6285

Sigma-Aldrich

17α,20β-Dihydroxy-4-pregnen-3-one

crystalline

Synonyme(s) :

17α,20β-Dihydroxyprogesterone, 17α-Hydroxy-20β-dihydroprogesterone, 4-Pregnene-17α,20β-diol-3-one, Maturation Inducing hormone (MIF)

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About This Item

Formule empirique (notation de Hill):
C21H32O3
Numéro CAS:
1662-06-2
Poids moléculaire :
332.48
Numéro MDL:
MFCD00010485
Code UNSPSC :
51111800
ID de substance PubChem :
24898755
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Pureté

≥98% (HPLC)

Forme

crystalline

Solubilité

ethanol: 50 mg/mL, clear, colorless to faintly yellow

Conditions d'expédition

ambient

Température de stockage

room temp

Chaîne SMILES 

O=C1CC[C@@]2(C)C(CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4(O)[C@@H](C)O)=C1

InChI

1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16-,17+,18+,19+,20+,21+/m1/s1

Clé InChI

MASCESDECGBIBB-FSHQYNQFSA-N

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Application

17α,20β-Dihydroxy-4-pregnen-3-one has been used as a fish pheromone candidate to study its effect on ciliated and microvillous olfactory receptor neurons. It has also been used as a chemical stimulant to study the behavioral and hormonal responses in focal male cichlid fish.

Actions biochimiques/physiologiques

17α,20β-Dihydroxy-4-pregnen-3-one, also known as maturation-inducing hormone (MIH) or DHP, is the most potent steroid for inducing final oocyte maturation in several species of fish. DHP as a progestin regulates spermiation, improves sperm motility and acts as a pheromone in male cyprinids.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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17, 20beta-Dihydroxy-4-pregnen-3-one
Handbook of Hormones: Comparative Endocrinology for Basic and Clinical Research, 509-510 (2016)
Y Pang et al.
Biology of reproduction, 61(4), 987-992 (1999-09-24)
Activin plays important roles in the regulation of vertebrate reproduction. Using zebrafish, Danio rerio, as a model, the present study aimed at investigating the role of activin in the regulation of final oocyte maturation. Administration of recombinant goldfish activin B
T Todo et al.
FEBS letters, 465(1), 12-17 (2000-01-06)
A cDNA encoding a nuclear 17alpha,20beta-dihydroxy-4-pregnen-3-one (17alpha,20beta-DP, spermiation-inducing hormone in fish) receptor (DPR) was, for the first time, isolated from an eel testis cDNA library. The amino acid sequence of DPR shows high homology with those of human and chicken
Irvin R Schultz et al.
Environmental toxicology and chemistry, 22(6), 1272-1280 (2003-06-06)
The synthetic estrogen 17 alpha-ethynylestradiol (EE2) is a commonly used oral contraceptive that has been increasingly detected in sewage effluents. This study determined whether EE2 exposure adversely affected reproduction in sexually maturing male rainbow trout (Oncorhynchus mykiss). We exposed male
M J Rocha et al.
Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology, 115(3), 257-264 (1996-11-01)
Female and male tilapia, Oreochromis mossambicus, were treated with luteinizing hormone-releasing hormone analogue (LH-RHa) and pimozide (PIM) or with human chorionic gonadotropin (hCG) to stimulate gonadal development and sexual maturation. Plasma (both sexes) and urine (males) samples were collected periodically
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