Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

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)

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
17, 20beta-Dihydroxy-4-pregnen-3-one
Handbook of Hormones: Comparative Endocrinology for Basic and Clinical Research, 509-510 (2016)
Shigeho Ijiri et al.
Endocrinology, 158(3), 627-639 (2016-12-15)
The maturation-inducing hormone 17α,20β-dihydroxy-4-pregnen-3-one (DHP) was first identified in the amago salmon. Although carbonyl reductase-like 20β-hydroxysteroid dehydrogenase (CR/20β-HSD) was reported to convert 17α-hydroxyprogesterone (17OHP) to DHP in rainbow trout, we previously found that CR/20β-HSD messenger RNA (mRNA) was not upregulated
Toshinobu Tokumoto et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(10), 3686-3690 (2004-03-03)
An endocrine-disrupting chemical, diethylstilbestrol (DES), a nonsteroidal estrogen, triggers oocyte maturation in fish. The morphology (the time course of the change in germinal vesicle breakdown) and an intracellular molecular event (the de novo synthesis of cyclin B) induced by DES
L O Afonso et al.
General and comparative endocrinology, 113(2), 221-229 (1999-03-20)
Plasma levels of 17beta-estradiol, 17alpha, 20beta-dihydroxy-4-pregnen-3-one (17alpha,20beta-P), and testosterone were measured in adult female coho salmon in late vitellogenesis, approximately 1.5 months before spawning and just before and following intraperitoneal injection with the aromatase inhibitor (AI) Fadrozole. Injection at dosages
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service