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ERGOSTA-4,7,22-TRIENE-3,6-DIONE

Year of first isolation: 1978
Formula:C28H40O2
Molecular weight:408
Occurence in plants:
Ganoderma lucidum [Fungi] » Images of Ganoderma lucidum Wikipedia: Ganoderma lucidum [Fungi]
Occurence in animals:
Raphidostila incisa [Porifera] » Images of Raphidostila incisa Wikipedia: Raphidostila incisa [Porifera]
ERGOSTA-4,7,22-TRIENE-3,6-DIONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2=CC(=O)C4=CC(=O)CCC34C)C
Isomeric SMILES
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C1[C@]2(C(=CC(=O)C1)C(=O)C=C1[C@@H]2CC[C@]2(C1CC[C@@H]2[C@H](C)/C=C/[C@@H](C(C)C)C)C)C  » JSMol: View in 3D
C1[C@]2(C(=CC(=O)C1)C(=O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@H](C)/C=C/[C@@H](C(C)C)C)C)C  » JSMol: View in 3D
C1[C@]2(C(=CC(=O)C1)C(=O)C=C1[C@@H]2CC[C@]2([C@@H]1CC[C@@H]2[C@H](C)/C=C/[C@@H](C(C)C)C)C)C » JSMol: View in 3D
IUPAC Name(10R,13R,17R)-17-[(E,2R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,9,11,12,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
CAS-RN 
PubChem CID23425004
InChiKey
[ ChemIDPlus: search ]
RMKUNHROPPZENV-RATFMIAWSA-N
InChIInChI=1S/C28H40O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-16-26(30)25-15-20(29)11-13-28(25,6)24(21)12-14-27(22,23)5/h7-8,15-19,22-24H,9-14H2,1-6H3/b8-7+/t18?,19-,22-,23?,24?,27-,28-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)408 [M]+ (80), 283 [M-side-chain]+ (100), 229 [M- C13H23]+ (33), 125 (13)
HR-MS408.3034, calcul. for C28H40O2 408.3028)

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 
28 
CDCl3
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.68 (s )
19-Me1.30 (s )
21-Me1.04 (d, 6.6)
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me0.82 (d, 6.6)
27-Me0.84 (d, 6.6)
28-Me0.92 (d, 6.6)

PHYSICAL PROPERTIES

M.P.156-159 °C
[α]D20 
IR (KBr) ν max (cm-1)2950, 2870 (CH), 1665 (CO), 1640 (CO), 1620 (C=C), 1600 (C=C
UV (EtOH) λ max (log ε)275 (3.8)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC, Nucleosil C18 (300 x 10 mm), MeOH 3 ml.min-1, Ret 12.2 min.

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationMALORNI, A. et al. (1978) Nouv. J. Chim. 2, 351-354 Search more
GeneralTURNER, W.B. et al. (1983) In: Fungal metabolites II, Academic Press, London, pp. 304-341 Search more
GeneralHIROTANI, M. et al. (1987) Phytochemistry 26, 2797-2803 Search more

see Important notice
© 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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