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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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[17alpha-Hydroxypregnenolone].
Yukiko Shimizu
Nihon rinsho. Japanese journal of clinical medicine, 68 Suppl 7, 367-370 (2010-10-22)
Shogo Haraguchi et al.
Endocrinology, 153(2), 794-805 (2011-12-01)
7α-Hydroxypregnenolone (7α-OH PREG) is a newly identified bioactive neurosteroid stimulating locomotor activity in the brain of newt, a wild animal, which serves as an excellent model to investigate the biosynthesis and biological action of neurosteroids. Here, we show that acute
Tamara S Hannon et al.
Journal of pediatric and adolescent gynecology, 25(1), 82-85 (2011-11-18)
Little is known about racial differences in androgen levels among obese children. The objective of this pilot study was to compare basal and stimulated androgen levels in a cross-sectional sample of obese black and white pubertal females. STUDY DESIGN, SETTING
Kazuyoshi Tsutsui et al.
General and comparative endocrinology, 168(2), 275-279 (2010-02-09)
We now know that steroids can be synthesized de novo by the brain and the peripheral nervous system. Such steroids are called neurosteroids and de novo neurosteroidogenesis from cholesterol is a conserved property of vertebrate brains. Our studies over the
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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