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

Year of first isolation: 2014
Formula:C29H46O7
Molecular weight:506
Occurence in plants:
Diplopterygium rufopilosum [Gleicheniaceae] » Images of Diplopterygium rufopilosum Wikipedia: Diplopterygium rufopilosum [Gleicheniaceae]
Occurence in animals:
 
2,3,14,20,26-PENTAHYDROXY-6-OXO-STIGMAST-7-ENE-22,26-LACTOL

STRUCTURE DESCRIPTORS

Canonical SMILESCCC1CC(OC(C1C)O)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@@H]1O[C@@H]([C@@H]([C@H](C1)CC)C)O)(C)O)O)C)C  » JSMol: View in 3D
(5b-H  » JSMol: View in 3D
epimer) » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-17-[(1R)-1-[(2R,4S,5R,6S)-4-ethyl-6-hydroxy-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 CID102236817
InChiKey
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FJOKKLPRYWQGHN-SMVDHQRDSA-N
InChIInChI=1S/C29H46O7/c1-6-16-11-24(36-25(33)15(16)2)28(5,34)23-8-10-29(35)18-12-20(30)19-13-21(31)22(32)14-26(19,3)17(18)7-9-27(23,29)4/h12,15-17,19,21-25,31-35H,6-11,13-14H2,1-5H3/t15-,16+,17+,19-,21-,22+,23+,24-,25+,26-,27-,28-,29-/m1/s1

MASS SPECTRUM

HRESI-MS (negative) [M-H] 505.3162 (calculated 505.3165 for C29H45O7)
EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z

CARBON NMR

PROTON NMR

CDCl3
0137.7 (t)
0268.0 (d)
0367.9 (d)
0431.1 (t)
0551.2 (d)
06203.7 (s)
07121.4 (d)
08165.1 (s)
0934.3 (d)
1038.5 (s)
1120.9 (t)
1231.9 (t)
1347.8 (s)
1484.0 (s)
1531.8 (t)
1621.5 (t)
1749.9 (d)
1817.8 (q)
1924.4 (d)
2075.9 (s)
2122.1 (q)
2274.1 (d)
2325.9 (t)
2431.0 (d)
2539.1 (d)
2698.9 (d)
2714.0 (d)
288.9 (t)
299.9 (q)
CDCl3
01-Ha1.38 (dd, 12.8, 3.8)
01-He1.78 (dd, 12.8, 2.8)
02-Ha3.87 (m)
03-He3.92 (m)
04-Ha1.61 (m)
04-He1.66 (m)
05-H2.41 (dd, 10.8, 3.8)
07-H5.73 (s)
09-H3.21 (dd, 10.8, 3.8)
11-Ha1.72 (m)
11-He1.74 (m)
12-Ha1.82 (m)
12-He2.21 (m)
15-Ha1.62 (m)
15-Hb2.00 (m)
16-Ha1.70 (m)
16-Hb1.73 (m)
17-H2.37 (dd, 10.8, 2.8)
18-Me0.90 (s)
19-Me0.94 (s)
21-Me1.25 (s)
22-H3.67 (dd, 10.8, 2.8)
23-Ha1.39 (ddd, 11.0, 3.2, 2.8)
23-Hb1.98 (ddd, 11.0, 10.8, 10.2)
24-H1.51 (ddd, 10.6, 10.2, 3.2)
25-H1.56 (ddd, 10.8, 10.6, 7.5)
26-H4.89 (d, 10.8)
27-Me0.85 (d, 7.5)
28-Ha1.12 (m)
28-Hb1.59 (m)
29-H0.85 (m)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D23.3-17.31 ° (c 0.054; MeOH)
IR (KBr) ν max (cm-1)3414 (OH), 2964, 2879, 1651 (carbonyl), 1547 (olefinic), 1462, 1059, 872
UV (CDCl3) λ max (log ε)242 (3.95) ;

CHROMATOGRAPHY

RP-HPLCcolumn 220 mm x 25 mm, 10 m, Merck C18, 15 mL/min, MeOH/H2O gradient 45 to 70%, retention time 18.7 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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