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D4202

Sigma-Aldrich

16-Dehydroprogesterone

97%

Synonym(s):

4,16-Pregnadiene-3,20-dione

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About This Item

Empirical Formula (Hill Notation):
C21H28O2
CAS Number:
1096-38-4
Molecular Weight:
312.45
EC Number:
214-142-8
MDL number:
MFCD00003651
UNSPSC Code:
12352115
PubChem Substance ID:
24893845
form:
powder
assay:
97%

assay

97%

form

powder

mp

185-187 °C (lit.)

SMILES string

[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)C(=CC[C@@]24[H])C(C)=O

InChI

1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h6,12,16,18-19H,4-5,7-11H2,1-3H3/t16-,18-,19-,20-,21+/m0/s1

InChI key

VRRHHTISESGZFN-RKFFNLMFSA-N

Gene Information

human ... CYP17A1(1586)

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pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
01116CF
00329DM
20130KG
12404BF

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T L Glass et al.
Journal of steroid biochemistry, 21(1), 65-72 (1984-07-01)
Eubacterium sp. 144 biotransformed 16-dehydroprogesterone by initially hydrating approx 50% to 16 alpha-hydroxyprogesterone. The detection of this reaction was dependent, in part, on the solubility state of 16-dehydroprogesterone and was less extensive when the concentration of methanol was insufficient to
Comparison of the cardiotonic response of ouabain, androstan-3-one, 16-dehydroprogesterone, and conjugated estrogens.
A Woods et al.
Proceedings of the Western Pharmacology Society, 34, 113-115 (1991-01-01)
T L Glass et al.
Applied and environmental microbiology, 49(5), 1146-1153 (1985-05-01)
Suspensions of Eubacterium sp. strain 144, prepared from cells grown with 16-dehydroprogesterone, catalyzed the reduction of this steroid to 17-isoprogesterone at a very low rate. Modifications of the assay to optimize the pH (5.5) and increase the steroid solubility (10%
Ismael Samudio et al.
Molecular cancer therapeutics, 4(12), 1982-1992 (2005-12-24)
In this study, the antileukemic effects of three isomeric pregnadienedione steroids [i.e., cis-guggulsterone, trans-guggulsterone, and 16-dehydroprogesterone] were investigated in HL60 and U937 cells as well as in primary leukemic blasts in culture. Our results show that all three compounds inhibited
D Stein et al.
The British journal of psychiatry : the journal of mental science, 163, 824-828 (1993-12-01)
Psychotic symptoms are not included under accepted definitions of premenstrual syndrome (PMS). We present a 14-year-old girl with PMS, who developed a late luteal cyclic psychosis during two consecutive premenstrual periods, which resolved completely after the onset of menses. She
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