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Year of first isolation: |
1985 |
| Formula: | C27H44O5 |
| Molecular weight: | 448 |
| Occurence in plants: |
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| Occurence in animals: |
Bombyx mori [Bombycidae] »  ![Wikipedia: Bombyx mori [Bombycidae]](/images/wikipedia.png)
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| Canonical SMILES | CC12CCC(CC1(C(C=C3C2CCC4(C3=CCC4C(C)(CCCC(C)(C)O)O)C)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | 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 » 
| | 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 CID | 101288317 | InChiKey
[ ChemIDPlus: search ] | SPQADBMKWOFZEK-XWTZGSRKSA-N | | InChI | nChI=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 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 448 (M)+, 145 (C8H17O2)+, 127, 109, 59, 43 | | HR-MS | |
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| 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 | |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | 4.64 (m ) | | 03-OH | 5.95 (d, 5) | | 04-Ha | 2.98 (dd, 13,5) | | 04-He | 2.02 (dd, 13,11) | | 06-H | 4.36 (br s ) | | 07-H | 6.06 (br t, 1.5) | | 09-Ha | 2.68 (br t, 10) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-H | 5.66 (br s ) | | 16-Ha | | | 16-Hb | 2.39 (ddd, 15,7.5,3.5) | | 17-H | 2.19 (dd, 11,7.5) | | 18-Me | 1.42 (s ) | | 19-Me | 1.12 (s ) | | 21-Me | 1.54 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.425 (s ) | | 27-Me | 1.425 (s ) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3400 (OH), 1638 (weak, diene) | | UV (EtOH) λ max (log ε) | 243 (?) |
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| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC, column Wakogel ODS-10K, solvent MeOH-H2O (61.5: 38.5) |
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Drosophila melanogaster BII cell assay: EC50 = >2.7 x 10-5M |
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Permanent link to this datasheet: BOMBYCOSTEROL
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