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ACETYLPINNASTEROL

Year of first isolation: 1981
Formula:C29H44O6
Molecular weight:488
Occurence in plants:
Laurencia pinnata [Rhodomelaceae] » Images of Laurencia pinnata Wikipedia: Laurencia pinnata [Rhodomelaceae]
Occurence in animals:
 
ACETYLPINNASTEROL

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2C1(CCC3C2=CC(=O)C4=CC(C(CC34C)OC(=O)C)O)C)O)O
Isomeric SMILES
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C1[C@]2(C(=C[C@H]([C@H]1OC(=O)C)O)C(=O)C=C1[C@@H]2CC[C@]2(C1CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name[(2S,3S,10R,13S)-17-[(2R,3S)-2,3-dihydroxy-6-methylheptan-2-yl]-3-hydroxy-10,13-dimethyl-6-oxo-1,2,3,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-2-yl] acetate
CAS-RN 
PubChem CID23424604
InChiKey
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RMENLPCGRPPGAV-TXXIXKGUSA-N
InChIInChI=1S/C29H44O6/c1-16(2)7-10-26(33)29(6,34)25-9-8-19-18-13-22(31)21-14-23(32)24(35-17(3)30)15-28(21,5)20(18)11-12-27(19,25)4/h13-14,16,19-20,23-26,32-34H,7-12,15H2,1-6H3/t19?,20?,23-,24-,25?,26-,27-,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z488 (M)+
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
28 
29 
C5D5N
01-Ha 
02-Ha5.34 (ddd, 10.5, 7, 3.5)
03-Ha4.71 (dd, 7, 2)
04-H6.82 (d, 2)
07-H6.03 (t, 2)
09-Ha2.54 (ddd, 12, 7, 2)
11-Ha 
11-He 
12-Ha 
12-He 
14-H2.21 (dt, 12, 2)
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.14 (s )
19-Me1.05 (s )
21-Me1.51 (s )
22-Ha3.74 (d, 9)
23-Ha 
24-Ha 
24-Hb 
25-H 
26-Me0.97 (d, 7)
27-Me0.98 (d, 7)
O-Ac2.05 (3H, s)
OH5.00 (3H, br s)

PHYSICAL PROPERTIES

M.P.105-107 °C
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLCRf 0.0 (MeOH-H2O 65:35) - RP-TLC on C18-bonded silica gel; Rf 0.0 (MeOH-H2O 50:50) - RP-TLC on paraffin-coated silica gel; Rf 0.68 (CHCl3-EtOH 80:20) NP-TLC on silica gel
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationFUKUZAWA, A. et al. (1981) Tetrahedron Lett., 4085-4086 Search more
GeneralWILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 Search more
GeneralFUKUZAWA, A. et al. (1986) Phytochemistry 25, 1305-1307 Search more

see Important notice
© 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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