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Merck
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P6285

Sigma-Aldrich

17α,20β-Dihydroxy-4-pregnen-3-one

crystalline

别名:

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

经验公式（希尔记法）:
C21H32O3
CAS号:
1662-06-2
分子量:
332.48
MDL编号:
MFCD00010485
UNSPSC代码:
51111800
PubChem化学物质编号:
24898755
NACRES:
NA.77
价格与库存信息目前不能提供

生物来源

synthetic (organic)

方案

≥98% (HPLC)

表单

crystalline

溶解性

ethanol: 50 mg/mL, clear, colorless to faintly yellow

运输

ambient

储存温度

room temp

SMILES字符串

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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应用

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.[1] It has also been used as a chemical stimulant to study the behavioral and hormonal responses in focal male cichlid fish.[2]

生化/生理作用

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.[3][4] DHP as a progestin regulates spermiation, improves sperm motility and acts as a pheromone in male cyprinids.[5]

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

历史批次信息供参考:

分析证书(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
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
K Sato et al.
Chemical senses, 26(9), 1145-1156 (2001-11-14)
Olfactory lamellae of teleosts contain two morphologically different types of olfactory receptor neurons (ORNs): ciliated ORNs (cORNs) and microvillous ORNs (mORNs). However, little is known about the functional difference between these two types of ORNs in fish olfaction. We isolated
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
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