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H5002

Sigma-Aldrich

17α-Hydroxypregnenolone

Synonym(s):

3β,17α-Dihydroxy-5-pregnen-20-one, 5-Pregnene-3β,17α-diol-20-one

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About This Item

Empirical Formula (Hill Notation):
C21H32O3
CAS Number:
387-79-1
Molecular Weight:
332.48
EC Number:
206-862-6
MDL number:
MFCD00021129
UNSPSC Code:
41116107
PubChem Substance ID:
24895665
NACRES:
NA.77

SMILES string

C[C@]1(CC[C@H](O)C2)C2=CC[C@]3([H])[C@]1([H])CC[C@@]4(C)[C@@]3([H])CC[C@@]4(C(C)=O)O

InChI

1S/C21H32O3/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/h4,15-18,23-24H,5-12H2,1-3H3

InChI key

JERGUCIJOXJXHF-UHFFFAOYSA-N

General description

17α-hydroxypregnenolone is a derived from pregnenolone.

Application

17α-hydroxypregnenolone has been used as a substrate for the enzyme 3β‐hydroxysteroid dehydrogenase (3β‐HSD) expressed in COS1 cells.

Biochem/physiol Actions

17α-hydroxypregnenolone acts as a precursor for cortisol and sex steroids.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Sung Mee Kim et al.
Clinical and experimental reproductive medicine, 42(2), 72-76 (2015-07-15)
17α-hydroxylase and 17,20-lyase are enzymes encoded by the CYP17A1 gene and are required for the synthesis of sex steroids and cortisol. In 17α-hydroxylase deficiency, there are low blood levels of estrogens, androgens, and cortisol, and resultant compensatory increases in adrenocorticotrophic
Akihiro Takemura et al.
General and comparative endocrinology, 175(1), 173-179 (2011-12-03)
Most wrasse species in tropical waters exhibit daily spawning synchrony with a preference for high tide. Fish perceive tidal rhythm cues through sensory organs and activate the brain-pituitary-gonadal endocrine axis for synchronous gonadal maturation, although how the tidal-related spawning cycle
Kazuyoshi Tsutsui et al.
Annals of the New York Academy of Sciences, 1163, 308-315 (2009-05-22)
It is now clearly established that steroids can be synthesized de novo by the brain and the peripheral nervous systems. Such steroids are called neurosteroids, and de novo neurosteroidogenesis from cholesterol is a conserved property of vertebrate brains. Our studies
Two novel HSD3B2 missense mutations with diverse residual enzymatic activities for Delta 5-steroids
TakasawaK, et al.
Clin. Endocrinol., 80(6), 782-789 (2014)
Toshiro Niwa et al.
Biological & pharmaceutical bulletin, 35(9), 1594-1597 (2012-09-15)
The effects of 21-hydroxypregnenolone and related steroids such as deoxycorticosterone (DOC; 21-hydroxyprogesterone), cortisol, and corticosterone on progesterone 17α-hydroxylase activity by steroidogenic cytochrome P450 c17 (CYP17) were investigated. 21-Hydroxypregnenolone contains a hydroxyl group at C3 in the A cyclic hydrocarbon ring
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