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24-OXO-22,23-DEHYDRO-20-HYDROXYECDYSONE

Year of first isolation: 2021
Formula:C27H40O7
Molecular weight:476
Occurence in plants:
Paris polyphylla var. yunnanensis [Melanthiaceae] » Images of Paris polyphylla var. yunnanensis Wikipedia: Paris polyphylla var. yunnanensis [Melanthiaceae]
Occurence in animals:
 
24-OXO-22,23-DEHYDRO-20-HYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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CC(C)(C(\C([H])=C([H])\[C@@](C)([C@H]3CC[C@]4(C2=CC([C@@H]1C[C@H]([C@H](C[C@]1(C)C2CC[C@]34C)O[H])O[H])=O)O[H])O[H])=O)O[H] » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17S)-17-((S,E)-2,6-dihydroxy-6-methyl-5-oxohept-3-en-2-yl)-2,3,14-trihydroxy-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 ]
KXOXJMJIPRGULB-NQYXCMQDSA-N
InChIInChI=1S/C27H40O7/c1-23(2,32)22(31)8-10-26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-9-25(21,27)4/h8,10,12,15,17,19-21,29-30,32-34H,6-7,9,11,13-14H2,1-5H3/b10-8+/t15?,17-,19+,20-,21-,24+,25+,26-,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z  
HRESIMS (negative ion mode) m/z499.2669 [M+Na]+, calculated 499.2672

CARBON NMR

PROTON NMR

CD3OD
0137.4
0268.7
0368.5
0432.9
0551.8
06206.5
07122.1
08167.8
0935.1
1039.3
1121.5
1232.2
1348.4
1485.1
1531.7
1622.8
1755.5
1818.8
1924.4
2077.0
2128.8
22156.5
23120.6
24205.1
2576.3
2626.5
2726.5
CD3OD
01-Ha1.78 (dd, 12.8, 3.7)
01-Hb1.41 (t, 12.8)
02-Ha3.82 (dt, 12.8, 3.7)
03-He3.94 (m)
04-Ha1.72 (m)
04-Hb1.69 (m)
05-H2.36 (dd, 13.0, 4.2)
07-H5.78 (d, 2.6)
09-H3.14 (m)
11-Ha1.78 (m)
11-Hb1.64 (m)
12-Ha2.13 (dt, 13.1, 4.8)
12-Hb1.90 (m)
15-Ha1.94 (m)
15-Hb1.61 (m)
16-Ha1.79 (m)
16-Hb?
17-H2.48 (9.5)
18-Me0.76 (s)
19-Me0.94 (s)
21-Me1.37 (s)
22-H7.14 (d, 15.5)
23-H6.88 (d, 15.5)
26-Me1.33 (s)
27-Me1.33 (s)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20+24.7° (c 0.08 ; MeOH)
IR (KBr) ν max (cm-1)3414, 2967, 1654, 1446, 1384, 1150, 1069
UV (MeOH) λ max (log ε)240 nm (2.63) ;

CHROMATOGRAPHY

HPTLC
TLC
GLC
HPLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationGUO, K. et al. (2021) Phytochemistry Letters 45, 117-120 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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