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P6285

Sigma-Aldrich

17α,20β-Dihydroxy-4-pregnen-3-one

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
MDL number:
MFCD00010485
UNSPSC Code:
51111800
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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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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