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P6285

17α,20β-Dihydroxy-4-pregnen-3-one

Name: 17&#945;,20&#946;-Dihydroxy-4-pregnen-3-one
Brand: SIGMA

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

Assay:

≥98% (HPLC)

Form:

crystalline

Quality level:

200

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Product Name

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

biological source

synthetic (organic)

Quality Level

200

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

Related Categories

Bioactive Small Molecules

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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17, 20beta-Dihydroxy-4-pregnen-3-one

Handbook of Hormones: Comparative Endocrinology for Basic and Clinical Research, 509-510 (2016)

A progestin (17α,20β-dihydroxy-4-pregnen-3-one) stimulates early stages of spermatogenesis in zebrafish.

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

Correlation between plasma steroid hormones and vitellogenin profiles and lunar periodicity in the female golden rabbitfish, Siganus guttatus (Bloch).

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

Effects of the aromatase inhibitor Fadrozole on plasma sex steroid secretion and ovulation rate in female coho salmon, Oncorhynchus kisutch, close to final maturation.

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

Roles of 11beta-hydroxysteroid dehydrogenase in fish spermatogenesis.

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

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Global Trade Item Number

SKU	GTIN
P6285-5MG	04061832851266
P6285-10MG	04061834393252
P6285-1MG	04061826236840

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