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STACHYSTERONE A 20,22-ACETONIDE

Year of first isolation: 2010
Formula:C30H46O6
Molecular weight:502
Occurence in plants:
Asparagus filicinus [Liliaceae] » Images of Asparagus filicinus
Occurence in animals:
 
STACHYSTERONE A 20,22-ACETONIDE

STRUCTURE DESCRIPTORS

Canonical SMILESCC1(OC(C(O1)(C)C2CCC3(C2=CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)CCC(C)(C)O)C
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC=C2[C@@]1(CC[C@@H]2[C@]1(C)[C@@H](CCC(C)(C)O)OC(O1)(C)C)C)C » JSMol: View in 3D
IUPAC Name2S,3R,5R,9R,10R,14S,17S)-2,3-dihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,14-dimethyl-1,2,3,4,5,9,11,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID46873731
InChiKey
[ ChemIDPlus: search ]
RTPYWSOTVUDJLP-VDDLBORISA-N
InChIInChI=1S/C30H46O6/c1-26(2,34)12-11-25-30(7,36-27(3,4)35-25)19-10-13-28(5)17(19)8-9-18-20(28)14-22(31)21-15-23(32)24(33)16-29(18,21)6/h8,14,18-19,21,23-25,32-34H,9-13,15-16H2,1-7H3/t18-,19-,21-,23+,24-,25+,28-,29+,30+/m0/s1

MASS SPECTRUM

HRESI-MS503.3372 [M+H]+, calculated for C29H47O6 503.3368
ESI-MS m/z 503.4 [M+H]+, 445.3 [M+H-C3H6O]+, 427.3 [M+H-C3H6O-H2O]+

CARBON NMR

PROTON NMR

CDCl3
(CH3)229.0, 27.3
-C(CH3)2106.6
0137.0
0267.7
0367.6
0431.2
0549.0
06202.6
07123.1
08173.9
0938.9
1039.9
1121.4
12120.8
13146.5
1448.4
1539.1
1625.6
1748.4
1825.2
1922.9
2084.2
2121.2
2281.0
2325.1
2441.4
2570.4
2629.6
2729.3
CDCl3
-C(CH3)21.45 (s), 1.36 (s)
01-Ha1.51 (t, 12)
01-He1.85 (d, 12)
02-Ha3.80 (m)
03-He4.06 (d, 2.5)
04-Ha1.66 (m)
04-He1.91 (m)
05-H2.42 (dd, 13.3, 4.2)
07-H2.94 (d, 2.7)
09-H2.59 (m)
11-Ha2.30 (m)
11-He2.01 (m)
12-H6.04 (m)
15-Ha1.95 (m)
15-Hb1.55 (m)
16-Ha1.84 (m)
16-Hb1.84 (m)
17-H2.80 (m)
18-Me1.16 (s)
19-Me0.97 (s)
21-Me1.24 (s)
22-H3.82 (m)
23-Ha1.68 (m)
23-Hb1.60 (m)
24-Ha1.78 (m)
24-Hb1.57 (m)
26-Me1.26 (s)
27-Me1.26 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25- 9.5 ° (c 0.055; MeOH)
IR (KBr) ν max (cm-1)3453 (OH), 2966, 2848, 1643 (unsaturated ketone), 1462, 1377 (gem dimethyl group), 1218, 1061
UV (EtOH) λ max (log ε)() ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationWU, J.-J. et al. (2010) Steroids 75, 734-739 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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