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125784

Sigma-Aldrich

trans-Dehydroandrosterone

97%

Synonym(s):

3β-Hydroxy-5-androsten-17-one, 5-Androsten-3β-ol-17-one, DHEA, Dehydroepiandrosterone, Dehydroisoandrosterone, Prasterone

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About This Item

Empirical Formula (Hill Notation):
C19H28O2
CAS Number:
53-43-0
Molecular Weight:
288.42
Beilstein:
2058110
EC Number:
200-175-5
MDL number:
MFCD00003613
UNSPSC Code:
12352103

Assay

97%

optical activity

[α]25/D +13.0°, c = 1 in ethanol

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

mp

149-151 °C (lit.)

SMILES string

C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@]34C)[C@@H]1CCC2=O

InChI

1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1

InChI key

FMGSKLZLMKYGDP-USOAJAOKSA-N

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Biochem/physiol Actions

Negative modulator of GABAA receptors. Steroid secreted by the adrenal gland with both estrogenic and androgenic properties. Its conversion to 5-androstenediol, a potent estrogen, enhances the growth and survival of estrogen-sensitive breast tumors. At high but physiologically valid concentrations, DHEA inhibits proliferation of chromaffin progenitor cells and induces dopaminergic differentiation.

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Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
15426KA
15123MS
12525CQ
03404DO
15726LO

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Marc-Antoine Bazin et al.
Bioorganic & medicinal chemistry, 15(9), 3152-3160 (2007-03-14)
Efficient syntheses of new DHEA analogues, and their apoptotic and necrotic effects on Leydig cells and TM4 Sertoli cells are described. The key step in the synthetic strategy of 7-amino-DHEA derivatives involves a bromination on C-7 position to give an
Artur T Cordeiro et al.
Bioorganic & medicinal chemistry, 18(13), 4762-4768 (2010-06-24)
Glucose 6-phosphate dehydrogenase (G6PDH) catalyzes the first step of the pentose-phosphate pathway which supplies cells with ribose 5-phosphate (R5P) and NADPH. R5P is the precursor for the biosynthesis of nucleotides while NADPH is the cofactor of several dehydrogenases acting in
Artur T Cordeiro et al.
Bioorganic & medicinal chemistry, 17(6), 2483-2489 (2009-02-24)
Dehydroepiandrosterone (DHEA) is known as an intermediate in the synthesis of mammalian steroids and a potent uncompetitive inhibitor of mammalian glucose-6-phosphate dehydrogenase (G6PDH), but not the enzyme from plants and lower eukaryotes. G6PDH catalyzes the first step of the pentose-phosphate
Leroy A Shervington et al.
European journal of medicinal chemistry, 44(7), 2944-2951 (2009-01-06)
Four ester prodrugs derived from the bifunctional alkylating agent chlorambucil, and one of its nitro-derivatives, 3-nitrochlorambucil conjugated to prasterone and pregnenolone, were synthesized and tested for their cytotoxic activity against eight human cell lines, using the standard MTT assay. A
Theodora Calogeropoulou et al.
Journal of medicinal chemistry, 52(21), 6569-6587 (2009-10-23)
DHEA analogues with modifications at positions C3 or C17 were synthesized and evaluated for neuroprotective activity against the neural-crest-derived PC12 cell model of serum deprivation-induced apoptosis. The most potent compounds were the spiro-epoxy derivatives 17beta-spiro[5-androstene-17,2'-oxiran]-3beta-ol (20), (20S)-3beta,21-dihydroxy-17beta,20-epoxy-5-pregnene (23), and (20R)-3beta,21-dihydroxy-17alpha,20-epoxy-5-pregnene
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