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PINNASTEROL

Year of first isolation: 1981
Formula:C27H42O5
Molecular weight:446
Occurence in plants:
Laurencia pinnata [Rhodomelaceae] » Images of Laurencia pinnata Wikipedia: Laurencia pinnata [Rhodomelaceae]
Occurence in animals:
 
PINNASTEROL

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2C1(CCC3C2=CC(=O)C4=CC(C(CC34C)O)O)C)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]		C1[C@]2(C(=C[C@@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2(C1CC[C@@H]2[C@@]([C@@H](CCC(C)C)O)(C)O)C)C  » JSMol: View in 3D
C1[C@]2(C(=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)(C)O)C)C  » JSMol: View in 3D
C1[C@]2(C(=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)(C)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3S,10R,13S,17S)-17-[(2R,3S)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3-dihydroxy-10,13-dimethyl-1,2,3,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID52931315
InChiKey
[ ChemIDPlus: search ]		NBEQHHTVOOYUFN-ORTBPADBSA-N
InChIInChI=1S/C27H42O5/c1-15(2)6-9-24(31)27(5,32)23-8-7-17-16-12-20(28)19-13-21(29)22(30)14-26(19,4)18(16)10-11-25(17,23)3/h12-13,15,17-18,21-24,29-32H,6-11,14H2,1-5H3/t17?,18?,21-,22-,23-,24-,25-,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)446 [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 
CD3OD
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
11-Ha 
11-He 
12-Ha 
12-He 
14-H 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me 
19-Me 
20-H 
21-Me 
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
25-H 
26-Me 
27-Me 

PHYSICAL PROPERTIES

M.P.198-201°C
[α]D20+ 37° (c ; MeOH)
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLCNP-TLC on silica gel Rf 0.56 (CHCl3-EtOH, 80:20); RP-TLC on paraffin-coated silica gel Rf 0.10 (MeOH-H2O, 50:50); RP-TLC on C18-bonded silica gel Rf 0.10 (MeOH-H2O, 65:35)
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationFUKUZAWA, A. et al. (1981) Tetrahedron Lett. (22), 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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