Skip to Content
MilliporeSigma
All Photos(1)

Documents

P6285

Sigma-Aldrich

17α,20β-Dihydroxy-4-pregnen-3-one

crystalline

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

Looking for similar products? Visit Product Comparison Guide

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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

Customers Also Viewed

Slide 1 of 8

1 of 8

[des-Gly10, D-Ala6]-LH-RH ethylamide acetate salt hydrate ≥97% (HPLC), powder

Sigma-Aldrich

L4513

[des-Gly10, D-Ala6]-LH-RH ethylamide acetate salt hydrate

Ethyl alcohol, Pure 190 proof, for molecular biology

Sigma-Aldrich

E7148

Ethyl alcohol, Pure

Ethyl acetate HPLC Plus, for HPLC, GC, and residue analysis, 99.9%

Sigma-Aldrich

650528

Ethyl acetate

Eosin Y Dye content ~99 %

Sigma-Aldrich

E4009

Eosin Y

Dichloromethane HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%, contains 50-150 ppm amylene as stabilizer

Sigma-Aldrich

650463

Dichloromethane

Progesterone ≥99%

Sigma-Aldrich

P0130

Progesterone

Melatonin powder, ≥98% (TLC)

Sigma-Aldrich

M5250

Melatonin

Hematoxylin certified by the Biological Stain Commission

Sigma-Aldrich

H3136

Hematoxylin

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
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
M D Rahman et al.
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology, 127(1), 113-122 (2000-01-11)
Characteristics of the lunar reproductive cycle in the golden rabbitfish, Siganus guttatus, were determined by histological observations of ovarian development, and immunological measurements of plasma steroid hormones, estradiol-17beta (E2), testosterone (T), 17alpha,20beta-dihydroxy-4-pregnen-3-one (DHP) and 17alpha,20beta,21-trihydroxy-4-pregnen-3-one (20beta-S), and vitellogenin (VTG). Ovarian
Yuichi Ozaki et al.
Endocrinology, 147(11), 5139-5146 (2006-08-05)
In fish spermatogenesis, the main action of progestins is generally regarded as the induction of sperm maturation. Our previous in vitro study demonstrated that a progestin, 17alpha,20beta-dihydroxy-4-pregnen-3-one (DHP), induced the initiation of meiosis in spermatogenesis in the Japanese eel (Anguilla
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