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H5752

Sigma-Aldrich

17α-Hydroxyprogesterone

≥95%

Sinónimos:

17α-Hydroxy-4-pregnene-3,20-dione, 4-Pregnen-17α-ol-3,20-dione

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About This Item

Fórmula empírica (notación de Hill):
C21H30O3
Número de CAS:
68-96-2
Peso molecular:
330.46
Beilstein/REAXYS Number:
3218109
EC Number:
200-699-4
MDL number:
MFCD00003659
UNSPSC Code:
51111800
PubChem Substance ID:
24278469
NACRES:
NA.77

biological source

synthetic (organic)

sterility

non-sterile

assay

≥95%

form

powder

solubility

chloroform: 50 mg/mL, clear, colorless to light yellow

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@@]4(C)[C@@]2([H])CC[C@]4(O)C(C)=O

InChI

1S/C21H30O3/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/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI key

DBPWSSGDRRHUNT-CEGNMAFCSA-N

Gene Information

human ... PGR(5241) , SERPINA6(866)
rat ... Ar(24208)

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General description

17α-Hydroxyprogesterone (17OHP) is a cortisol precursor and is synthesized from progesterone by the action of enzyme 17α-hydroxylase. 17OHP is a poor ligand for the nuclear progesterone receptor and an antagonist for mineralocorticoid receptor.

Application

17α-Hydroxyprogesterone has been used:
  • for titration against ovarian S9 protein in thin-layer chromatography
  • as a substrate for hydroxysteroid dehydrogenase from B. megaterium cultures
  • as a cortisone analog to test its effect on voltage-dependent potassium channels (Kv1)

Biochem/physiol Actions

17α-Hydroxyprogesterone (17OHP) is converted to 11-deoxycortisol in the presence of enzyme 21-hydroxylase. Deficiency of 21-hydroxylase results in the accumulation of 17OHP. High levels of 17OHP are observed in congenital adrenal hyperplasia (CAH).

related product

Referencia del producto
Descripción
Precios

pictograms

Health hazardEnvironment
GHS08,GHS09

signalword

Danger

Hazard Classifications

Aquatic Chronic 2 - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Steroid biosynthetic enzyme activities in leachate-exposed female perch (Perca fluviatilis) as biomarkers for endocrine disruption
Linderoth M, et al.
The Science of the Total Environment, 366(2-3) (2006)
Potentiation of the Kv1 family K+ channel by cortisone analogues
Pan Y, et al.
ACS Chemical Biology, 7(10) (2012)
Influence of 17-hydroxyprogesterone, progesterone and sex steroids on mineralocorticoid receptor transactivation in congenital adrenal hyperplasia
Mooij CF, et al.
Hormone Research in p?diatrics, 83(6) (2015)
Genetic engineering of Bacillus megaterium for high-yield production of the major teleost progestogens 17alpha, 20beta-di-and 17alpha, 20beta, 21alpha-trihydroxy-4-pregnen-3-one
Gerber A, et al.
Metabolic engineering, 36 (2016)
Non-genomic progesterone actions in female reproduction
Gellersen B, et al.
Human Reproduction Update, 15(1) (2009)
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