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DACRYSTERONE

Year of first isolation: 1973
Formula:C28H46O8
Molecular weight:510
Occurence in plants:
Dacrydium intermedium [Podocarpaceae] » Images of Dacrydium intermedium Wikipedia: Dacrydium intermedium [Podocarpaceae]
Occurence in animals:
 
DACRYSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C)O)O)O)C(C)(C)O
Isomeric SMILES
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C1[C@]2([C@@](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](C[C@H](C(C)(C)O)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN50299-45-1
PubChem CID102239719
InChiKey
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LMQKRCYKYDRRFC-KDZLJHQNSA-N
InChIInChI=1S/C28H46O8/c1-15(23(2,3)33)11-21(31)26(6,34)20-8-10-27(35)17-12-22(32)28(36)14-19(30)18(29)13-25(28,5)16(17)7-9-24(20,27)4/h12,15-16,18-21,29-31,33-36H,7-11,13-14H2,1-6H3/t15-,16+,18+,19-,20+,21-,24-,25-,26-,27-,28-/m1/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)492 [M-18]+ (1), 474 (2), 456 (3), 438 (3), 379 (50), 361 (47), 343 (23), 325 (25), 189 (20), 140 (22), 131 (13), 113 (100), 105 (26), 95 (66), 93 (20), 91 (25), 85 (28), 83 (23), 70 (96)
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
0134.7
0267.9
0369.7
0435.8
0579.7
06200.7
07119.8
08166.8
0938.2
1044.7
1121.2
1231.6
1348.1
1484.0
1532.0
1622.0
1749.8
1817.8
1917.0
2076.9
2121.5
2274.7
2334.5
2441.7
2572.1
2626.4 *
2728.2 *
2815.3
C5D5N
01-Ha 
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-Me1.22
19-Me1.15
21-Me1.56
22-Hb 
23-Ha 
24-Ha 
24-Hb 
25-H 
26-Me1.32
27-Me1.32
28-Me1.07 (d, 6)

PHYSICAL PROPERTIES

M.P.283-285°C
[α]D20 
IR (KBr) ν max (cm-1)1690 (cyclohexenone)
UV (EtOH) λ max (log ε)240 (4.056)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silicagel Rf 0.20 (CHCl3-EtOH 4:1) (makisterone A 0.16); Rf 0.27 (CHCl3-EtOH 4:1); RP-TLC on paraffin coated silica gel Rf 0.37 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.39 (MeOH-H2O 65:35)
GLCRet 9.85 min on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationRUSSEL, G.B. et al. (1973) Aust. J. Chem. 26, 1805-1807 Search more
GeneralBLUNT, J.W. et al. (1979) Aust. J. Chem. 32, 779-782 Search more
GeneralWILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 Search more
GeneralBIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 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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