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P6285

Sigma-Aldrich

17α,20β-Dihydroxy-4-pregnen-3-one

crystalline

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Synonym(s):
17α,20β-Dihydroxyprogesterone, 17α-Hydroxy-20β-dihydroprogesterone, 4-Pregnene-17α,20β-diol-3-one, Maturation Inducing hormone (MIF)
Empirical Formula (Hill Notation):
C21H32O3
CAS Number:
1662-06-2
Molecular Weight:
332.48
MDL number:
MFCD00010485
UNSPSC Code:
12352200
PubChem Substance ID:
24898755
NACRES:
NA.77

biological source

synthetic (organic)

Assay

≥98% (HPLC)

form

crystalline

solubility

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

shipped in

ambient

storage temp.

room temp

SMILES string

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

InChI key

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.

Biochem/physiol Actions

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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17, 20beta-Dihydroxy-4-pregnen-3-one
Handbook of Hormones: Comparative Endocrinology for Basic and Clinical Research, 509-510 (2016)
Shi X Chen et al.
General and comparative endocrinology, 185, 1-9 (2013-01-31)
Recently, evidence has been provided for multiple regulatory functions of progestins during the late mitotic and meiotic phases of spermatogenesis in teleost fish. For example, our previous studies suggested that 17α,20β-dihydroxy-4-pregnen-3-one (DHP), potentially via Sertoli cells that express the progesterone
H Kagawa et al.
General and comparative endocrinology, 112(1), 80-88 (1998-09-28)
The effects of red seabream gonadotropins (PmGTH I and PmGTH II) on the induction in vitro of germinal vesicle breakdown (GVBD) and the development of maturational competence (responsiveness to maturation-inducing steroid) were examined in the oocytes of red seabream. PmGTH
T Wu et al.
Biology of reproduction, 62(6), 1585-1592 (2000-05-20)
Activins, inhibins, and follistatins are important regulators of mammalian reproduction. However, their roles in lower vertebrates are poorly understood. In this study, we examined the expression of activin A, inhibin A, and follistatins in the zebrafish ovary and determined their
M J Rocha et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 125(1), 85-91 (2002-01-16)
Ovarian samples from fear sea bass, Dicentrarchus labrax, were collected for the in vitro incubations during the spawning period. Follicles with fully developed vitellogenic oocytes showing central germinal vesicle (stage I follicles) and follicles with oocytes showing initial germinal vesicle
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