H5002
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:
Molecular Weight:
332.48
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.77
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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.[1]
Application
17α-hydroxypregnenolone has been used as a substrate for the enzyme 3β‐hydroxysteroid dehydrogenase (3β‐HSD) expressed in COS1 cells.[2]
Biochem/physiol Actions
17α-hydroxypregnenolone acts as a precursor for cortisol and sex steroids.[1]
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
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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
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
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
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