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Merck
CN

125784

反式-脱氢雄甾酮

97%

别名:

3β-羟基-5-雄烯-17-酮, DHEA, 去氢表雄酮, 普拉睾酮, 脱氢异雄酮, 雄素-5-烯-3β-醇-17-酮

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关于此项目

经验公式(希尔记法):
C19H28O2
化学文摘社编号:
分子量:
288.42
EC Number:
200-175-5
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
2058110
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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

GABAA 受体的负调节剂。肾上腺分泌的具有雌激素和雄激素特性的类固醇。类固醇转变为 5-雄烯二醇,一种强效的雌激素,促进雌激素敏感性乳腺肿瘤的生长和存活。
GABAA 受体的负调节剂。肾上腺分泌的类固醇,具有雌激素和雄激素特性。 它转化为 5-雄烯二醇(一种有效的雌激素)可增强雌激素敏感性乳腺肿瘤的生长和存活率。在高浓度但生理有效的条件下,DHEA 抑制嗜铬细胞祖细胞的增殖并诱导多巴胺能分化。

signalword

Warning

pictograms

Health hazard

hcodes

Hazard Classifications

Repr. 2

存储类别

13 - Non Combustible Solids

wgk

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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分析证书(COA)

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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
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

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