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Year of first isolation: |
2008 |
| Formula: | C30H48O8 |
| Molecular weight: | 536 |
| Occurence in plants: |
Leuzea carthamoides [Asteraceae] »  ![Wikipedia: Leuzea carthamoides [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1(OC(C(O1)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(C(C(C(C5)O)O)O)C)C)O)CCC(C)(C)O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3([C@@H]([C@@H]([C@@H](C4)O)O)O)C)[C@@]1(CC[C@@H]2[C@@]5([C@H](OC(O5)(C)C)CCC(C)(C)O)C)O » 
| | IUPAC Name | (1S,2R,3R,5R,9R,10R,13R,14S,17S)-1,2,3,14-tetrahydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 70684796 | InChiKey
[ ChemIDPlus: search ] | HJVDUXDOWYFHPW-VDDNSLTKSA-N | | InChI | InChI=1S/C30H48O8/c1-25(2,35)11-10-22-29(7,38-26(3,4)37-22)21-9-13-30(36)17-14-19(31)18-15-20(32)23(33)24(34)28(18,6)16(17)8-12-27(21,30)5/h14,16,18,20-24,32-36H,8-13,15H2,1-7H3/t16-,18-,20+,21-,22+,23+,24+,27+,28+,29+,30+/m0/s1 |
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| EI-MS m/z (relative intensity %) | | | HRESI-MS m/z | 559.3243 [M+Na]+ (calculated for C30H48O8 Na : 559.3247) | | CI-MS (NH3) m/z | | | ESI-MS/MS m/z | 537 [M+H]+, 519 [M+H-H20]+, 501 [M+H-2H20]+, 479 [M+H-C3H6O]+, 461 [M+H-C3H6O-H2O]+, 443 [M+H-C3H6O-2H2O]+, 425 [M+H-C3H6O-3H2O]+, |
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| CD3OD | | 01 | 76.41 | | 02 | 68.49 | | 03 | 70.98 | | 04 | 33.49 | | 05 | 46.79 | | 06 | 205.58 | | 07 | 122.18 | | 08 | 166.85 | | 09 | 35.68 | | 10 | 43.75 | | 11 | 21.89 | | 12 | 32.31 | | 13 | 49.0* | | 14 | 85.15 | | 15 | 31.74 | | 16 | 22.33 | | 17 | 51.53 | | 18 | 17.67 | | 19 | 20.07 | | 20 | 85.83 | | 21 | 22.58 | | 22 | 83.30 | | 23 | 24.70 | | 24 | 42.21 | | 25 | 71.11 | | 26 | 29.34 | | 27 | 29.49 | | 2xCH3 | 28.95, 27.18 | | OCO | 108.03 |
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| CD3OD | | 01-He | 3.82 (b) | | 02-Ha | 3.87 (t, 3.1, 3.1) | | 03-He | 4.04 (b) | | 04-Ha | 1.81 | | 04-He | 1.78 | | 05-H | 2.61 (dd, 12.4, 4.4) | | 07-H | 5.84 (d, 2.4) | | 09-Ha | 3.07 (bt) | | 11-Ha | 1.70 | | 11-He | 1.73 | | 12-Ha | 2.09 (td, 13, 13, 5) | | 12-He | 1.83 | | 15-Ha | 1.97 | | 15-Hb | 1.62 | | 16-Ha | 1.87 | | 16-Hb | 2.04 | | 17-H | 2.31 (dd, 9.2, 8.4) | | 18-Me | 0.840 (s) | | 19-Me | 1.074 (s) | | 21-Me | 1.175 (s) | | 22-H | 3.68 (dd, 8.2, 3.5) | | 23-Ha | 1.52 | | 23-Hb | 1.52 | | 24-Ha | 1.73 | | 24-Hb | 1.49 | | 26-Me | 1.195 (s) | | 27-Me | 1.204 (s) | | Me2C= | 1.39 (s), 1.32 (s) |
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| M.P. | °C ; | | [α]D20 | + 31.6 ° (c 0.23; EtOH) | | IR (KBr) ν max (cm-1) | 3401 (OH), 1655 (C=O), 1177, 1062 (C-O) | | UV (MeOH) λ max (log ε) | |
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| HPLC | RP-HPLC Separon SGX C-18 (250 x 4 mm), solvent methanol-water (linear grad of 10-70%), flow-rate 0,6 ml/min (Ret 55.0 min); NP-HPLC Silasorb 600 (250 x 4 mm) solvent dichloromethane-isopropanol-water (84:15:1), flow-rate 0.8 ml/min (Ret 28.0 min); and two other systems. | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: INTEGRISTERONE A 20,22-ACETONIDE
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