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Merck
CN

125784

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
EC Number:
200-175-5
UNSPSC Code:
12352103
MDL number:
MFCD00003613
Beilstein/REAXYS Number:
2058110

Key Documents

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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

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.
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.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361fd

Hazard Classifications

Repr. 2

Storage Class

13 - Non Combustible Solids

wgk

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
15726LO
15601CI
11408JB
10130AQ
08711BB

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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
Javier A Ramírez et al.
Bioorganic & medicinal chemistry, 15(24), 7538-7544 (2007-09-26)
In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation
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
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