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H5752

Sigma-Aldrich

17α-Hydroxyprogesterone

≥95%

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
Beilstein:
3218109
EC Number:
200-699-4
MDL number:
MFCD00003659
UNSPSC Code:
51111800
PubChem Substance ID:
24278469
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

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).

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Description
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Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Statements

H360FD,H411

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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)
Linder, N., et al.
Archives of Disease in Childhood. Fetal and Neonatal Edition, 81, 175-175 (1999)
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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