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2,3,14,20-TETRAHYDROXY-26-METHOXY-6-OXO-STIGMAST-7-ENE-22,26-LACTOL

Year of first isolation: 2014
Formula:C30H48O7
Molecular weight:520
Occurence in plants:
Diplopterygium rufopilosum [Gleicheniaceae] » Images of Diplopterygium rufopilosum Wikipedia: Diplopterygium rufopilosum [Gleicheniaceae]
Occurence in animals:
 
2,3,14,20-TETRAHYDROXY-26-METHOXY-6-OXO-STIGMAST-7-ENE-22,26-LACTOL

STRUCTURE DESCRIPTORS

Canonical SMILESCCC1CC(OC(C1C)OC)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H]1O[C@@H]([C@@H]([C@H](C1)CC)C)OC)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-17-[(1R)-1-[(2R,4S,5R,6S)-4-ethyl-6-methoxy-5-methyloxan-2-yl]-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID102236816
InChiKey
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FRONTTDPNNXTHP-HJPBRRLISA-N
InChIInChI=1S/C30H48O7/c1-7-17-12-25(37-26(36-6)16(17)2)29(5,34)24-9-11-30(35)19-13-21(31)20-14-22(32)23(33)15-27(20,3)18(19)8-10-28(24,30)4/h13,16-18,20,22-26,32-35H,7-12,14-15H2,1-6H3/t16-,17+,18+,20-,22-,23+,24+,25-,26+,27-,28-,29-,30-/m1/s1

MASS SPECTRUM

HRESI-MS (negative) [M-H] 519.3328 (caclulated 519.3322 for C30H47O7)
EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

CDCl3
0137.7 (t)
0268.1 (d)
0368.1 (d)
0431.3 (t)
0551.2 (d)
06203.0 (s)
07121.9 (d)
08164.9 (s)
0934.5 (d)
1038.7 (s)
1121.3 (t)
1232.2 (t)
1348.2 (s)
1484.1 (s)
1531.7 (t)
1621.3 (t)
1750.0 (d)
1818.0 (q)
1924.4 (d)
2076.0 (s)
2122.2 (q)
2274.2 (d)
2326.1 (t)
2431.2 (d)
2536.3 (d)
26103.1 (d)
2714.3 (d)
2826.1 (t)
2910.2 (q)
OCH354.9 (q)
CDCl3
01-Ha1.36 (dd, 12.6, 3.8)
01-He1.75 (dd, 12.6, 2.8)
02-Ha3.84 (m)
03-He3.90 (m)
04-Ha1.60 (m)
04-He1.65 (m)
05-H2.38 (dd, 10.8, 3.8)
07-H5.70 (br, s)
09-H3.18 (dd, 10.8, 3.8)
11-Ha1.69 (overlapped)
11-He1.72 (overlapped)
12-Ha1.89 (m)
12-He2.18 (m)
15-Ha1.62 (m)
15-Hb1.96 (m)
16-Ha1.69 (pverlapped)
16-Hb1.72 (overlapped)
17-H2.34 (dd, 10.8, 2.8)
18-Me0.90 (s)
19-Me0.93 (s)
21-Me1.23 (s)
22-H3.65 (dd, 10.8, 2.8)
23-Ha1.37 (ddd, 11.0, 3.2, 2.8)
23-Hb1.95 (ddd, 11.0, 10.8, 10.2)
24-H1.49 (ddd, 10.6, 10.2, 3.2)
25-H1.79 (ddd, 10.8, 10.6, 7.5)
26-H4.53 (d, 10.8)
27-Me0.84 (d, 7.5)
28-Ha1.11 (m)
28-Hb1.60 (m)
29-H0.83 (m)
OCH33.30 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D23.3-11.10 ° (c 0.032; MeOH)
IR (KBr) ν max (cm-1)3441 (OH), 2942, 2873, 1715 (carbonyl), 1630 (olefinic), 1451, 1389, 1094
UV (CDCl3) λ max (log ε)242 (3.75) ;

CHROMATOGRAPHY

RP-HPLCcolumn 220 mm x 25 mm, 10 m, Merck C18, 15 mL/min, MeOH/H2O gradient 45 to 70%, retention time 15.6 min.
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationHU, J. et al. (2014) Phytochemistry Letters 8, 73-76 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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