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26-HYDROXYINTEGRISTERONE A

Year of first isolation: 2009
Formula:C27H44O9
Molecular weight:512
Occurence in plants:
Silene frivaldskyana [Caryophyllaceae] » Images of Silene frivaldskyana Wikipedia: Silene frivaldskyana [Caryophyllaceae]
Occurence in animals:
 
26-HYDROXYINTEGRISTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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[C@@H]1([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](CCC(CO)(C)O)O)O)O)C)C)O  » JSMol: View in 3D
[C@@H]1([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](CC[C@@](CO)(C)O)O)O)O)C)C)O  » JSMol: View in 3D
[C@@H]1([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](CC[C@](CO)(C)O)O)O)O)C)C)O » JSMol: View in 3D
IUPAC Name(1S,2R,3R,5R,9R,10R,13R,14S,17S)-1,2,3,14-tetrahydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl)-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
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AWDTWBCMHQMBAR-GRKWQUQLSA-N
InChIInChI=1S/C27H44O9/c1-23(34,13-28)8-7-20(31)26(4,35)19-6-10-27(36)15-11-17(29)16-12-18(30)21(32)22(33)25(16,3)14(15)5-9-24(19,27)2/h11,14,16,18-22,28,30-36H,5-10,12-13H2,1-4H3/t14-,16-,18+,19-,20+,21+,22+,23?,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

HR-MS
EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z 530 [M+NH4]+, 512 [M]+ (100), 494, 477, 456, 378, 360

CARBON NMR

PROTON NMR

D2O
0176.9
0269.8
0371.5
0434.3
0547.8
06n.d.
07123.6
08n.d.
0937.0
1045.0
1122.7
1233.5
1349.7
1487.6
1532.8
1622.5
1751.7
1819.5
1921.4
2080.5
2122.1
2279.8
2327.7
2438.0
2575.7
2671.3
2724.4, 24.9 (2 epimers)
D2O
01-He3.93 (s, br, w1/2 = 11)
02-Ha4.05 (t, 1)
03-He4.15 (s, br, w1/2 = 9)
04-Ha1.82
04-He1.82
05-H2.63 (t, 9.2)
07-H6.00 (d, 2.1)
09-Ha3.04 (s, br, w1/2 = 22)
11-Ha1.77
11-He1.78
12-Ha1.96
12-He1.96
15-Ha1.67
15-Hb2.06 (m)
16-Ha1.88*
16-Hb1.78*
17-H2.32 (t, 9.9)
18-Me 
19-Me 
20-H 
21-Me 
22-H3.43 (d, 10)
23-Ha1.34
23-Hb1.66
24-Ha1.76
24-Hb1.48 (t, d, 13.4, 3.9)
26-CH20H3.47
26-Me 
27-Me1.17 (s), 1.18 (s) (2 epimers)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)242 () ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationZIBAREVA, L. et al. (2009) Arch. Insect Biochem. Physiol. 72, 234-248 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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