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Merck

H5752

17α-Hydroxyprogesterone

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C21H30O3
CAS Number:
68-96-2
Molecular Weight:
330.46
NACRES:
NA.77
PubChem Substance ID:
24278469
UNSPSC Code:
51111800
EC Number:
200-699-4
MDL number:
MFCD00003659
Beilstein/REAXYS Number:
3218109

Product Name

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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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

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

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF6121V
WXBF4110V
WXBF4687V
WXBF2175V
MKCR5907

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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)
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)
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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