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14β,17α-14-DEOXYPOSTSTERONE

Year of first isolation: 2021
Formula:C21H30O4
Molecular weight:346
Occurence in plants:
Cyanotis arachnoidea [Commelinaceae] » Images of Cyanotis arachnoidea Wikipedia: Cyanotis arachnoidea [Commelinaceae]
Occurence in animals:
 
14β,17α-14-DEOXYPOSTSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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[ ChemSpider: search ]
CC(=O)[C@@H]1CC[C@H]2[C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O[H])O[H])C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13S,14S,17R)-17-acetyl-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
OGEJBBPFFLOZKJ-ANYXFMRHSA-N
InChIInChI=1S/C21H30O4/c1-11(22)13-4-5-14-12-8-17(23)16-9-18(24)19(25)10-21(16,3)15(12)6-7-20(13,14)2/h8,13-16,18-19,24-25H,4-7,9-10H2,1-3H3/t13-,14+,15-,16-,18+,19-,20+,21+/m0/s1

MASS SPECTRUM

HRESIMS (positive ion mode) m/z 347.22157 [M+H]+, calculated for C21H31O4 347.22169

CARBON NMR

PROTON NMR

DMSO-d6
0136.5
0266.8
0366.7
0432.0
0550.1
06202.1
07124.0
08164.2
0934.2
1037.6
1120.6
1226.9
1345.2
1455.9
1529.9
1623.9
1763.1
1824.2
1924.2
20208.8
2131.6
DMSO-d6
01-Hɑ1.60
01-Hβ1.24 (t, 12.5)
02-Hɑ3.74
03-Hɑ3.74
04-Hɑ1.44
04-Hβ1.48
05-Hɑ2.16 (dd,12.5, 4.3)
05-Hβ2.16 (dd,12.5, 4.3)
07-H5.68 (d, 2.4)
09-H2.75 (ddd, 12.0, 5.0, 2.0)
11-Hɑ1.70
11-Hβ1.34
12-Hɑ1.55
12-Hβ1.15
14-Hɑ2.47 (t, 9.5)
14-Hβ2.47 (t, 9.5)
15-Hɑ1.84
15-Hβ1.69
16-Hɑ2.10
16-Hβ1.71
17-Hɑ2.85 (t, 9.5)
17-Hβ2.85 (t, 9.5)
18-Me1.14 (s)
19-Me0.80 (s)
21-Me2.11 (s)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D25+29.3° (c 0.096 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)245 nm (-) ;

CHROMATOGRAPHY

HPLC
HPTLC
GLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTÓTH G., HERKE et al. (2021) J. Nat. Prod. 84, 1870–1881 Search more

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© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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