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24,25-DEHYDROINOKOSTERONE

Year of first isolation: 2011
Formula:C27H42O7
Molecular weight:478
Occurence in plants:
Chenopodium quinoa [https://en.wikipedia.org/wiki/Lygodium] » Images of Chenopodium quinoa Wikipedia: Chenopodium quinoa [https://en.wikipedia.org/wiki/Lygodium]
Occurence in animals:
 
24,25-DEHYDROINOKOSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)CO
Isomeric SMILES
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[ ChemSpider: search ]
C1[C@]2([C@@H](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=C(/C)CO)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(E,2R,3R)-2,3,7-trihydroxy-6-methylhept-5-en-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID102415267
InChiKey
[ ChemIDPlus: search ]
RNTVQJZHDDLTKJ-LJFSBTINSA-N
InChIInChI=1S/C27H42O7/c1-15(14-28)5-6-23(32)26(4,33)22-8-10-27(34)17-11-19(29)18-12-20(30)21(31)13-24(18,2)16(17)7-9-25(22,27)3/h5,11,16,18,20-23,28,30-34H,6-10,12-14H2,1-4H3/b15-5+/t16-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

HR-MS
EI-MS m/z (relative intensity %)
CI-MS (NH3) m/z 496 [M+H+NH3]+, 479 [M+H]+, 461 [M+H-H2O]+, 443 [M+H-2H2O]+, 425 [M+H-3H2O]+, 363, 345, 329, 327

CARBON NMR

PROTON NMR

D2O
0137.8
0269.9
0369.9
0434.0
0552.5
06*
07123.6
08*
0936.2
1040.6
1122.9
1233.5
1350.0
1487.5
1533.2
1622.9
1752.1
1819.8
1925.6
2080.3
2122.3
2279.2
2332.8
24126.7
25138.9
2670.1
2715.9
D2O
01-Ha1.37 (t, 13)
01-He1.87
02-Ha3.97 (m, w1/2 = 22)
03-He4.07 (m, w1/2 = 7)
04-Ha1.76
04-He1.76
05-H2.34 (t)
07-H5.97 (d, 2.4)
09-H3.11 (m, w1/2 = 23)
11-Ha1.74
11-He1.85
12-Ha1.98
12-He1.98
15-Ha1.65
15-Hb2.04
16-Ha1.82
16-Hb1.89
17-H2.34 (t, 9.3)
18-Me0.86 (s)
19-Me1.000 (s)
21-Me1.271 (s)
22-H3.55 (dd, 9.9, 2.9)
23-Ha2.39
23-Hb2.13
26-CH2-4.01 (s)
27-Me1.69 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20° (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)() ;

CHROMATOGRAPHY

HPLC
GLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKUMPUN, S. et al. (2011) Food Chemistry 125, 1226-1234 Search more

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