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3-EPI-20,26-DIHYDROXYECDYSONE

Year of first isolation: 1979
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
 
Occurence in animals:
Manduca sexta [Lepidoptera] » Images of Manduca sexta Wikipedia: Manduca sexta [Lepidoptera]
Pieris brassicae [Lepidoptera] » Images of Pieris brassicae Wikipedia: Pieris brassicae [Lepidoptera]
3-EPI-20,26-DIHYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]		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](CCC(CO)(C)O)O)O)O)C)C  » JSMol: View in 3D
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](CCC(CO)(C)O)O)O)O)C)C  » JSMol: View in 3D
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](CCC(CO)(C)O)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3S,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-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
[ ChemIDPlus: search ]		RRCGNPRHZQPOOT-NLQGZBTGSA-N
InChIInChI=1S/C27H44O8/c1-23(33,14-28)8-7-22(32)26(4,34)21-6-10-27(35)16-11-18(29)17-12-19(30)20(31)13-24(17,2)15(16)5-9-25(21,27)3/h11,15,17,19-22,28,30-35H,5-10,12-14H2,1-4H3/t15-,17-,19-,20-,21-,22+,23?,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z478 (M-18)+
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
C5D5N
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.22
19-Me1.07
21-Me1.58
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me--
27-Me1.48

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC on silicaRf 0.27 (CHCl3-EtOH 65:35 v/v) (2026E : 0.22)
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKAPLANIS, J.N. et al. (1979) Steroids 34, 333-345 Search more
GeneralLAFONT, R. et al. (1980) Steroids 36, 185-207 Search more
GeneralWARREN, J.T. et al. (1986) J. Liq. Chromatogr. 9, 1759-1782 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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