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(2β,3α,5β,14α,22R)-2,3,20,22,25-PENTAHYDROXYCHOLEST-7-ENE-6-ONE

Year of first isolation: 2008
Formula:C27H44O6
Molecular weight:464
Occurence in plants:
Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: Serratula wolffii [Asteraceae]
Occurence in animals:
 
(2β,3α,5β,14α,22R)-2,3,20,22,25-PENTAHYDROXYCHOLEST-7-ENE-6-ONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1CCC2C(C)(C(CCC(C)(C)O)O)O
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[C@]2([C@H]1CC[C@@H]2[C@@]([C@@H](CCC(C)(C)O)O)(C)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3S,5R,9R,10R,13S,14R,17S)-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID102478941
InChiKey
[ ChemIDPlus: search ]
KBDUJCBPMFPAJU-DLKCTXPZSA-N
InChIInChI=1S/C27H44O6/c1-24(2,32)10-9-23(31)27(5,33)22-7-6-16-15-12-19(28)18-13-20(29)21(30)14-26(18,4)17(15)8-11-25(16,22)3/h12,16-18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,17-,18-,20-,21-,22-,23+,25-,26+,27+/m0/s1

MASS SPECTRUM

HR-ESI-MS464.3129, calculated 464.3126 for C27H44O6+
CI-MS (NH3) m/z
ESI-MS m/z (relative intensity %)503 (25) [M+K]+, 487 (100) [M+Na]+, 465 (45) [M+H]+, 447 (46) [M+H-H2O]+, 429 (17) [M+H-2H2O]+, 411 (24) [M+H-3H2O]+

CARBON NMR

PROTON NMR

CD3OD
0143.1
0272.2
0375.4
0434.1
0557.5
06204.2
07122.3
08168.5
0940.3
1039.6
1123.1
1240.6
1347.0
1457.2
1523.6
1622.8
1756.4
1814.8
1924.3
2077.8
2121.1
2278.4
2327.4
2442.5
2571.5
2629.0
2730.0
CD3OD
01-Ha1.09 (dd, 13.9, 11.8)
01-He2.09 (dd, 13.3, 3.3)
02-Ha3.62 (ddd, 11.3, 8.7, 5.1)
03-Ha3.34 (ddd, 11.7, 8.7, 4.5)
04-Ha1.47 (td, 13.1, 11.3)
04-He1.74-1.81 (m)
05-H2.08 (dd, 13.8, 4.3)
07-H5.65 (d, 2.1)
09-H2.66 (ddd, 11.6, 6.9, 2.4)
11-Ha1.75-1.80 (m)
11-He1.88-1.95 (m)
12-Ha1.56-1.64 (m)
12-He2.31 (ddd, 13.1, 4.0, 3.0)
14-He2.22 (ddd, 11.7, 6.2, 1.6)
15-Ha1.56-1.63 (m)
15-Hb1.68-1.72 (m)
16-Ha1.96-2.02 (m)
16-Hb1.69-1.73 (m)
17-H1.82 (t, 9.2)
18-Me0.83 (s)
19-Me0.96 (s)
21-Me1.23 (s)
22-H3.29-3.34 (m)
23-Ha1.27-1.35 (m)
23-Hb1.65 (ddd, 12.0, 4.3, 1.6)
24-Ha1.38-1.47 (m)
24-Hb1.75-1.84 (m)
26-Me1.19 (s)
27-Me1.21 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D25+14 ° (c 0.05; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)246 (3.744)

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationSIMON, A. et al. (2008) Helv. Chim. Acta 91, 1640-1645 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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