H5752

17α-Hydroxyprogesterone

≥95%

• Synonym(s): 17α-Hydroxy-4-pregnene-3,20-dione, 4-Pregnen-17α-ol-3,20-dione
• Empirical Formula (Hill Notation): C₂₁H₃₀O₃
• CAS Number: 68-96-2
• Molecular Weight: 330.46
• Beilstein: 3218109
• EC Number: 200-699-4
• MDL number: MFCD00003659
• UNSPSC Code: 51111800
• PubChem Substance ID: 24278469
• NACRES: NA.77

Properties

• 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)

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)

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).

Safety Information

• Pictograms: GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H360FD,H411
• Precautionary Statements: P202 - P273 - P280 - P308 + P313 - P391 - P405
• Hazard Classifications: Aquatic Chronic 2 - Repr. 1B
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves