H5752

17α-Hydroxyprogesterone

Name: 17α-Hydroxyprogesterone
Brand: SIGMA

synthetic (organic), ≥95%, cortisol precursor, powder

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 CAS:

68-96-2

Peso molecular:

330.46

NACRES:

NA.77

PubChem Substance ID:

24278469

UNSPSC Code:

51111800

EC Number:

200-699-4

MDL number:

MFCD00003659

Beilstein/REAXYS Number:

3218109

Nombre del producto

17α-Hydroxyprogesterone, ≥95%

InChI key

DBPWSSGDRRHUNT-CEGNMAFCSA-N

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

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

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

Quality Level

200

Gene Information

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

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Categorías relacionadas

Pequeñas moléculas bioactivas

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).

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.

pictograms

GHS08,GHS09

signalword

Danger

hcodes

H360FD,H411

pcodes

P202 - P273 - P280 - P308 + P313 - P391 - P405

Hazard Classifications

Aquatic Chronic 2 - Repr. 1B

Clase de almacenamiento

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

wgk

WGK 3

ppe

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

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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)

Potentiation of the Kv1 family K+ channel by cortisone analogues

Pan Y, et al.

ACS Chemical Biology, 7(10) (2012)

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)

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)

Aldosterone activates NF-kappaB in the collecting duct.

Valérie Leroy et al.

Journal of the American Society of Nephrology : JASN, 20(1), 131-144 (2008-11-07)

Besides its classical effects on salt homeostasis in renal epithelial cells, aldosterone promotes inflammation and fibrosis and modulates cell proliferation. The proinflammatory transcription factor NF-kappaB has been implicated in cell proliferation, apoptosis, and regulation of transepithelial sodium transport. The effect

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