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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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
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
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
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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