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RHAPOCASTERONE A

Year of first isolation: 2020
Formula:C29H44O9
Molecular weight:536
Occurence in plants:
Rhaponticum acaule [Asteraceae] » Images of Rhaponticum acaule
Occurence in animals:
 
RHAPOCASTERONE A

STRUCTURE DESCRIPTORS

Isomeric SMILES
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C[C@@]12[C@@](C(C=C3C2[C@H](O)C[C@@]4(C)[C@@]3(O)CC[C@@H]4[C@](C)([C@H](O[C@H](O)[C@@H]/5O)CC5=C(C)/C)O)=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,11R,13R,14S,17S)-17-((R)-1-((2R,5R,6S)-5,6-dihydroxy-4-(propan-2-ylidene)tetrahydro-2H-pyran-2-yl)-1-hydroxyethyl)-2,3,11,14-tetrahydroxy-10,13-dimethyl-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 ]
OCWFUZDLPYVGLK-HZSVVOAMSA-N
InChIInChI=1S/C29H44O9/c1-13(2)14-8-22(38-25(35)24(14)34)28(5,36)21-6-7-29(37)16-10-17(30)15-9-18(31)19(32)11-26(15,3)23(16)20(33)12-27(21,29)4/h10,15,18-25,31-37H,6-9,11-12H2,1-5H3/t15-,18+,19-,20+,21-,22+,23?,24+,25-,26-,27+,28+,29+/m0/s1

MASS SPECTRUM

HRESIMS (negative ion mode) m/z535.2901 [M-H]–, (positive mode 537.3053 [M+H]+, , and 559.2871 [M+Na]+, , calc. for C29H44O9 536.2985

CARBON NMR

PROTON NMR

CD30D
0139.0
0268.9
0368.5
0433.2
0552.7
06206.7
07122.7
08168.7
0942.8
1039.9
1169.4
1243.6
1348.3
1484.9
1531.8
1621.7
1750.4
1819.2
1924.6
2077.1
2121.6
2281.5
2326.1
24129.4
25130.9
2620.08
2720.59
2868.5
2997.3
CD30D
01-Ha1.39 (dd, 12.7, 12.7)
01-Hb2.88 (ss, 12.7, 5.0)
02-Ha4.02 (ddd, 12.0, 7.0, 3.4)
03-He3.96 (br s)
04-Ha1.78
04-Hb1.70
05-H2.34 (dd, 13.2, 2.9)
07-H5.81 (d, 2.2)
09-H3.16 (dd, 9.0, 2.5)
11-H4.11 (ddd, 15.8, 10.2, 6.6)
12-HaZ.Z2 (dd "t", 12.0, 12.0)
12-Hb2.10 (dd;, 12.0, 6.3)
15-Ha1.97 (m)
15-Hb1.60 (m)
16-Ha1.99
16-Hb1.75
17-H2.43 (ss "t", 8.3)
18-Me0.84 (s)
19-Me1.06 (s)
21-Me1.33 (s)
22-H3.19 (dd, 12.1, 2.0)
23-Ha2.48 (dd)
23-Hb2.08 (dd)
26-Me1.80 (d, 1.6)
27-Me1.75 (s)
28-H4.41 (d, 1.2)
29-H4.51 (d, 1.2)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20+32.3° (c 0.124 ; MeOH)
IR (KBr) ν max (cm-1)3370, 2963, 29.34, 1648, 1443, 1377, 1032
UV (MeOH) λ max (log ε)230 nm (-) ;

CHROMATOGRAPHY

TLC
GLC
HPTLC
HPLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationZUGHDANI, M. et al. (2020) Phytochemistry 180, 112530 Search more

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