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Year of first isolation: |
2007 |
| Formula: | C28H42O6 |
| Molecular weight: | 474 |
| Occurence in plants: |
Serratula wolffii [Asteraceae] »  ![Wikipedia: Serratula wolffii [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1(C(=C)CC(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(C1OC(C(=C)C1)(C)C)O)O)C)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(C1OC(C(=C)C1)(C)C)O)O)C)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(C1OC(C(=C)C1)(C)C)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(1R)-1-[(2R)-5,5-dimethyl-4-methylideneoxolan-2-yl]-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101431681 | InChiKey
[ ChemIDPlus: search ] | IPJLOFDOKBDRGY-IJYGRGDZSA-N | | InChI | InChI=1S/C28H42O6/c1-15-11-23(34-24(15,2)3)27(6,32)22-8-10-28(33)17-12-19(29)18-13-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h12,16,18,20-23,30-33H,1,7-11,13-14H2,2-6H3/t16-,18-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1 |
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| HRESI-MS | 474.2975 (calculated for C28H42O6 474.2970) | | CI-MS (NH3) m/z | | | ESI-MS m/z (relative intensity %) | 497 (10) [M+Na]+, 475 (100) [M+H]+, 457 (72) [M+H-H2O]+, 439 (5.7) [M+H-2H2O]+, 421 (3) [M+H-3H2O]+, 364 (2) |
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| CD3OD | | 01 | 37.5 | | 02 | 68.9 | | 03 | 68.7 | | 04 | 33.2 | | 05 | 51.9 | | 06 | 206.6 | | 07 | 122.3 | | 08 | 168.1 | | 09 | 35.3 | | 10 | 39.4 | | 11 | 21.6 | | 12 | 32.45 | | 13 | 48.4 | | 14 | 85.4 | | 15 | 31.8 | | 16 | 22.0 | | 17 | 52.0 | | 18 | 18.35 | | 19 | 24.5 | | 20 | 76.8 | | 21 | 20.7 | | 22 | 82.4 | | 23 | 35.6 | | 24 | 158.3 | | 25 | 83.2 | | 26 | 27.9 | | 27 | 29.7 | | 28 CH2= | 104.1 |
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| CD3OD | | 01-Ha | 1.43 (dt, 13.1, 12.5) | | 01-He | 1.795 | | 02-Ha | 3.84 (ddd, 12.1, 4.3, 3.3) | | 03-He | 3.95 (q, 2.9) | | 04-Ha | 1.72* | | 04-He | 1.76* | | 05-H | 2.38 (dt, 8.1, 4.7) | | 07-H | 5.81 (d, 2.7) | | 09-H | 3.15 (ddd, 11.3, 7.1, 2.7) | | 11-Ha | 1.67 | | 11-He | 1.80 | | 12-Ha | 2.165 (td, 13.3, 4.8) | | 12-He | 1.84 | | 15-Ha | 1.62 | | 15-Hb | 1.97 | | 16-Ha | 1.83 | | 16-Hb | 2.00 | | 17-H | 2.42 (dd, 9.5, 8.2) | | 18-Me | 0.84 (s) | | 19-Me | 0.96 (s) | | 21-Me | 1.21 (s) | | 22-H | 3.91 (t, 8.1) | | 23-Ha | 2.545 (dt, 8.2, 2.2) | | 23-Hb | 2.545 (dt, 8.2, 2.2) | | 26-Me | 1.28 (s) | | 27-Me | 1.33 (s) | | 28 CH2= | 4.805 (t, 2.3), 4.895 (t, 2.2) |
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| M.P. | - °C ; | | [α]D28 | +3 ° (c 0.05 ; MeOH) ; different for Japonicone (isomeric ?) | | UV (MeOH) max (log ) | 241.8 (3.7) ; | | IR (KBr) ν max (cm-1) | |
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| HPLC | NP-HPLC, solvent cyclohexane-isopropanol-water 100:40:3; RP-HPLC, solvent methanol-water 60:40. | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 24-METHYLENESHIDASTERONE
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