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H5752 Sigma-Aldrich

17α-Hydroxyprogesterone

≥95%

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

  • CAS Number 68-96-2

  • Empirical Formula (Hill Notation) C21H30O3

  • Molecular Weight 330.46

  •  Beilstein/REAXYS Number 3218109

  •  EC Number 200-699-4

  •  MDL number MFCD00003659

  •  PubChem Substance ID 24278469

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Cytokines, Growth Factors and Hormones,
Quality Level   200
biological source   synthetic (organic)
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)

Description

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)

Packaging

5, 25 g in poly bottle

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).

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
TU5060000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

HPLC Analysis of Steroids on Ascentis® Express Biphenyl

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Steroids on Ascentis® Express Biphenyl
Keywords: Chromatography, High performance liquid chromatography

Peer-Reviewed Papers
15

References

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Description

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738093 17α-Hydroxyprogesterone-2,3,4-13C3, 98 atom % 13C, 98% (CP)

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