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CALONYSTERONE

Year of first isolation: 1973
Formula:C27H40O7
Molecular weight:476
Occurence in plants:
Ipomoea calonyction [Convolvulaceae] » Images of Ipomoea calonyction Wikipedia: Ipomoea calonyction [Convolvulaceae]
Occurence in animals:
 
CALONYSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3=C(C1=CCC2C(C)(C(CCC(C)(C)O)O)O)C(=O)C(=C4C3(CC(C(C4)O)O)C)O
Isomeric SMILES
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C1[C@]2(C(=C(C(=O)C3=C2CC[C@]2(C3=CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)C)O)C[C@H]([C@H]1O)O)C » JSMol: View in 3D
IUPAC Name(2S,3R,10R,13R,17S)-2,3,6-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-one
CAS-RN51787-31-6
PubChem CID101281312
InChiKey
[ ChemIDPlus: search ]
XAKKXZNYERXAIY-HTYOSDJUSA-N
InChIInChI=1S/C27H40O7/c1-24(2,33)10-9-20(30)27(5,34)19-7-6-14-21-15(8-11-25(14,19)3)26(4)13-18(29)17(28)12-16(26)22(31)23(21)32/h6,17-20,28-31,33-34H,7-13H2,1-5H3/t17-,18+,19+,20-,25+,26-,27-/m1/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)476 (14.4), 458 (32.4), 443 (18.0), 442 (16.2), 440 (38.8), 425 (22.8), 424 (9.2), 422 (18.2), 407 (12.8), 406 (5.9), 359 (56.5), 343 (48), 342 (100), 341 (59.1), 327 (93.1), 325 (41.0), 323 (39.2), 315 (64.2), 314 (80.5), 298 (75.8), 296 (40.5), 161, 143, 125, 107, 99, 81, 69, 55
HR-MS476.2774 (M)+ (14.4%), calc. 476.2774 for C27H40O7)
CI/D477 (M+H)+, 459, 441, 427, 425, 423, 376, 361, 359, 345, 343, 341

CARBON NMR

PROTON NMR

DMSO-d6
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
1484.2
15 
16 
17 
18 
19 
2074.9
21 
2276.4
2320.0
24 
2568.6
2629.8
2729.8
C5D5N
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-H7.41 (m, w1/2 = 4)
16-Ha 
16-Hb 
17-H 
18-Me1.40 (s )
19-Me1.72 (s )
21-Me1.56 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.42 (s )
27-Me1.42 (s )
DMSO-d6
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-H6.78
16-Ha 
16-Hb 
17-H 
18-Me1.00
19-Me1.41
21-Me1.16
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.05
27-Me1.07

PHYSICAL PROPERTIES

M.P.234-235 °C
[α]D20+76.8 ° (c 1; MeOH)
IR (KBr) ν max (cm-1)3380, 3350 (OH), 1638, 1620, 845 (C=C, C=O conj.)
UV (EtOH) λ max (log ε)222 (4.32), 233(4.13), 294 (3.89)

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silica gel Rf 0.42 (CHCl3-EtOH 4:1); RP-TLC on paraffin coated silica gel Rf 0.32 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.28 (MeOH-H2O 65:35)
GLCRet 10.5 min on 1.5% OV 101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C for 60 h.
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: inactive

REFERENCES

First isolationCANONICA, L. et al. (1973) J. Chem. Soc., Chem. Commun., 737-738 Search more
GeneralCANONICA, L. et al. (1975) Phytochemistry 14, 525-527 Search more
GeneralCANONICA, L. et al. (1977) Gazz. Chim. Ital. 107, 229-235 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
GeneralSUKSAMRARN, A. et al. (1994) Tetrahedron 35, 4445-4448 Search more
SynthesisSUKSAMRARN, A. et al. (1997) Phytochemistry 45, 1149-1152 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 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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