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PUNICESTERONE B

Year of first isolation: 2022
Formula:C31H50O6
Molecular weight:518
Occurence in plants:
Aspergillus puniceus [Fungi] » Images of Aspergillus puniceus Wikipedia: Aspergillus puniceus [Fungi]
Occurence in animals:
 
PUNICESTERONE B

STRUCTURE DESCRIPTORS

Isomeric SMILES
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C[C@@]12[C@@](C(C=C3C2CC[C@@]4(C)[C@@]3(O)CC[C@@]4([C@@]5(C)OC(C)(C)O[C@@H]5C[C@@H](C)C(C)C)[H])=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17S)-17-((4R,5R)-5-((R)-2,3-dimethylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl)-2,3,14-trihydroxy-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 ]
OHZSMTMLHURXAU-USZHUNGWSA-N
InChIInChI=1S/C31H50O6/c1-17(2)18(3)13-26-30(8,37-27(4,5)36-26)25-10-12-31(35)20-14-22(32)21-15-23(33)24(34)16-28(21,6)19(20)9-11-29(25,31)7/h14,17-19,21,23-26,33-35H,9-13,15-16H2,1-8H3/t18-,19?,21+,23-,24+,25+,26-,28-,29-,30-,31-/m1/s1

MASS SPECTRUM

HRESIMS (positive ion mode) m/z 519.3682 (M+H)+, calculated for C31H51O6 519.3680

CARBON NMR

PROTON NMR

DMSO-d6
0136.6
0266.8
0366.6
0432.0
0550.1
06202.7
07120.5
08164.6
0933.2
1037.6
1120.0
1230.6
1346.7
1483.0
1530.2
1620.9
1748.4
1816.7
1923.9
2084.0
2121.7
2278.3
2332.5
2435.3
2532.2
2617.8
2720.0
2814.7
29106.0
3026.7
3129.0
DMSO-d6
01-Ha1.27 (d, 12.8)
01-Hb1.59
02-Ha3.60 (m)
03-He 3.76 (br, s)
04-Ha1.47 (m)
04-Hb1.59 (m)
05-H2.22 (dd, 13.2, 4.0)
07-H5.63 (d, 1.5)
09-H2.99 (t, 8.3)
11-Ha1.51 (m)
11-Hb1.64 (m)
12-Ha1.68 (m)
12-Hb2.01 (td, 12.8, 4.5)
15-Ha1.53 (m)
15-Hb1.79 (dd, 18.5, 11.8)
16-Ha1.71 (m)
16-Hb1.87 (dd, 20.3, 10.9)
17-H2.14 (t, 8.9)
18-Me0.69 (s)
19-Me0.82 (s)
21-Me1.06 (s)
22-H3.68 (d, 10.4)
23-Ha1.00 (t, 11.9)
23-Hb1.41 (t, 12.0)
24-H1.47
25-H1.55 (m)
26-Me0.79 (d, 6.8)
27-Me0.84 (d, 6.8)
28-Me0.78 (d, 6.4)
30-Me1.24 (s)
31-Me1.31 (s)
[02-OH]4.37 (d, 5.8)
[03-OH]4.37 (d, 2.3)
[14-OH]4.78 (s)

PHYSICAL PROPERTIES

M.P.257-259 °C ;
[α]D25+60° (c 0.1 ; MeOH)
IR (film) ν max (cm-1)3335, 2047, 2831, 1651, 1448, 1415, 1232, 1116, 1022, 885, 736
UV (MeOH) λ max (log ε)243 nm (3.98)

CHROMATOGRAPHY

 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationHUANG, Z.-H. et al. (2022) Phytochemistry 205, 113511 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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