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14-HYDROXYPINNASTEROL

Year of first isolation: 1986
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Laurencia pinnata [Rhodomelaceae] » Images of Laurencia pinnata Wikipedia: Laurencia pinnata [Rhodomelaceae]
Occurence in animals:
 
14-HYDROXYPINNASTEROL

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4=CC(C(CC34C)O)O)C)O)O)O
Isomeric SMILES
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C1[C@]2(C(=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](CCC(C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3S,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,9,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 162902990
InChiKey
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QTZCCMVFFNRYMG-OUAVXPTCSA-N
InChIInChI=1S/C27H42O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h12-13,15-16,20-23,29-33H,6-11,14H2,1-5H3/t16-,20-,21-,22-,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %) 
FD-MS462 [M]+, 444, 351, 317, 145

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 
C5D5N
01-Ha 
01-Hb 
02-Ha4.21 (ddd, 10, 7, 3.5)
03-Ha4.64 (dd, 7, 2)
04-H6.79 (d, 2)
05-H--
07-H6.28 (d, 2)
09-Ha3.54 (ddd, 12, 7, 2)
11-Ha 
11-He 
12-Ha 
12-He 
14-H--
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H2.94 (t, 9)
18-Me1.22 (s )
19-Me1.26 (s )
21-Me1.59 (s )
22-Hb3.83 (d, 11)
23-Ha 
24-Ha 
24-Hb 
25-H 
26-Me0.84 (d, 6.7)
27-Me0.85 (d, 6.7)

PHYSICAL PROPERTIES

M.P.210-212 °C
[α]D20+39° (c 0.35 ; MeOH)
IR (KBr) ν max (cm-1)3450, 1685, 1655, 1075
UV (EtOH) λ max (log ε)256 (3.88)

CHROMATOGRAPHY

TLC 
GLC 
HPLCpreparative on Hitachi-gel #3011 (MeOH-H2O, 4:1)
LCpreparative silica gel (Merck, 70-230 mesh), fraction eluting with EtOAc-MeOH (1:1)

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationFUKUZAWA, 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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