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Merck
CN

P6285

17α,20β-Dihydroxy-4-pregnen-3-one

synthetic (organic), ≥98% (HPLC), Maturation inducing hormone, crystalline

Synonym(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

Empirical Formula (Hill Notation):
C21H32O3
CAS Number:
1662-06-2
Molecular Weight:
332.48
UNSPSC Code:
51111800
PubChem Substance ID:
24898755
NACRES:
NA.77
MDL number:
MFCD00010485

Key Documents

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Product Name

17α,20β-Dihydroxy-4-pregnen-3-one, crystalline

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 key

MASCESDECGBIBB-FSHQYNQFSA-N

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

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

Quality Level

200

Related Categories

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000411746
0000411746
0000243522
0000243511
0000232159

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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
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
S T Lee et al.
General and comparative endocrinology, 112(1), 1-9 (1998-09-28)
The in vitro metabolism of [3H]17-hydroxyprogesterone by spermatozoa of primary and 17alpha-methyltestosterone (MT)-induced secondary male grouper (Epinephelus coioides) has been examined. With only the labeled precursor, the four predominant 5beta-pregnanes (17, 20alpha-dihydroxy-5beta-pregnan-3-one; 5beta-pregnan-3alpha,17, 20alpha-triol; 3alpha,17-dihydroxy-5beta-pregnan-20-one; and 17hydroxy-5beta-pregnan-3,20-dione) accounted for 75%
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
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