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ALFREDENSTEROL

Year of first isolation: 2017
Formula:C31H48O6
Molecular weight:516
Occurence in plants:
Laurencia alfredensis [Rhodomelaceae] » Images of Laurencia alfredensis Wikipedia: Laurencia alfredensis [Rhodomelaceae]
Occurence in animals:
 
ALFREDENSTEROL

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C1[C@]2([C@H](C[C@H]([C@H]1OC(=O)C)OC(=O)C)C(=O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@H](C)[C@@H](CCC(C)C)O)C)C  » JSMol: View in 3D
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structure) » JSMol: View in 3D
IUPAC Name(2beta,3beta,5alpha,22R)-22-Hydroxy-6-oxocholest-7-ene-2,3-diyl diacetate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
YDJFQXQEYWCOLA-RCNOFZQISA-N
InChIInChI=1S/C31H48O6/c1-17(2)8-11-26(34)18(3)22-9-10-23-21-14-27(35)25-15-28(36-19(4)32)29(37-20(5)33)16-31(25,7)24(21)12-13-30(22,23)6/h14,17-18,22-26,28-29,34H,8-13,15-16H2,1-7H3/t18-,22+,23-,24-,25+,26+,28+,29-,30+,31+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z
HR-ESI-MS 517.3527 [MH]+, calculated 517.3529 for C31H49O6
EI-MS m/z (relative intensity %)

CARBON NMR

PROTON NMR

CDCl3
0136.7
0268.5
0368.5
0421.2
0548.7
06199.6
07123.3
08162.5
0950.6
1037.7
1121.5
1238.7
1344.8
1455.1
1522.6
1626.9
1753.3
1812.3
1914.9
2042.4
2112.6
2273.7
2327.8
2436.0
2528.1
2622.4
2722.9
CH3-{C}O-169.3 169.5
{CH}3-CO-21.1 21.2
CDCl3
01-Ha1.72 (m)
01-He2.00 (m)
02-Ha4.93 (m)
03-He5.04 (m)
04-Ha1.93 (ddd, 2.6, 12.6, 15.4)
04-He2.10 (m)
05-H2.58 (dd, 3.5, 12.5)
07-H5.75 (m)
09-H2.35 'ddd, 2.5, 6.9, 9.9)
11-Ha1.62 (m)
11-He1.40 (m)
12-Ha1.40 (m)
12-He2.14 (m)
14-H2.05 (m)
15-Ha1.53 (m)
15-Hb1.64 (m)
16-Ha1.44 (m)
16-Hb1.80 (m)
17-H1.33 (m)
18-Me0.61 (s)
19-Me0.96 (s)
20-H1.68 (m)
21-Me0.94 (d, 6.8)
22-H3.62 (dd, 1.6, 10.1)
23-Ha1.24 (m)
23-Hb1.36 (m)
24-Ha1.17 (m)
24-Hb1.39 (m)
25-H1.55 (m)
26-Me0.89 (d, 6.8)
27-Me0.90 (d, 6.8)
CH3-CO-2.03 (s), 2.04 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D2022.0 ° (c 0.13 ; CHCl3)
IR (KBr) ν max (cm-1)3425, 2925, 1737, 1643, 1350, 1234, 1035
UV (MeOH) λ max (log ε)239 (3.43) ;

CHROMATOGRAPHY

GLC
HPTLC
HPLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationDZIWORNU, G.A. et al. (2017) Molecules 22, 513 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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