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BOMBYCOSTEROL

Year of first isolation: 1985
Formula:C27H44O5
Molecular weight:448
Occurence in plants:
 
Occurence in animals:
Bombyx mori [Bombycidae] » Images of Bombyx mori Wikipedia: Bombyx mori [Bombycidae]
BOMBYCOSTEROL

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC(CC1(C(C=C3C2CCC4(C3=CCC4C(C)(CCCC(C)(C)O)O)C)O)O)O
Isomeric SMILES
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C1[C@]2([C@](C[C@H](C1)O)([C@H](C=C1[C@@H]2CC[C@]2(C1=CC[C@@H]2[C@](C)(CCCC(C)(C)O)O)C)O)O)C » JSMol: View in 3D
IUPAC Name(3S,5R,6S,9S,10R,13R,17S)-17-[(2S)-2,6-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,6,9,11,12,16,17-decahydrocyclopenta[a]phenanthrene-3,5,6-triol
CAS-RN 
PubChem CID101288317
InChiKey
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SPQADBMKWOFZEK-XWTZGSRKSA-N
InChInChI=1S/C27H44O5/c1-23(2,30)11-6-12-26(5,31)21-8-7-19-18-15-22(29)27(32)16-17(28)9-14-25(27,4)20(18)10-13-24(19,21)3/h7,15,17,20-22,28-32H,6,8-14,16H2,1-5H3/t17-,20-,21-,22-,24-,25+,26-,27-/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)448 (M)+, 145 (C8H17O2)+, 127, 109, 59, 43
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 
C5D5N
01-Ha 
01-He 
02-Ha 
03-He4.64 (m )
03-OH5.95 (d, 5)
04-Ha2.98 (dd, 13,5)
04-He2.02 (dd, 13,11)
06-H4.36 (br s )
07-H6.06 (br t, 1.5)
09-Ha2.68 (br t, 10)
11-Ha 
11-He 
12-Ha 
12-He 
15-H5.66 (br s )
16-Ha 
16-Hb2.39 (ddd, 15,7.5,3.5)
17-H2.19 (dd, 11,7.5)
18-Me1.42 (s )
19-Me1.12 (s )
21-Me1.54 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.425 (s )
27-Me1.425 (s )

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3400 (OH), 1638 (weak, diene)
UV (EtOH) λ max (log ε)243 (?)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLCRP-HPLC, column Wakogel ODS-10K, solvent MeOH-H2O (61.5: 38.5)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = >2.7 x 10-5M

REFERENCES

First isolationFUJIMOTO, Y. et al. (1985) Chem. Commun., 10-12 Search more
BioactivitiesDINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 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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