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Year of first isolation: |
1992 |
| Formula: | C30H48O7 |
| Molecular weight: | 520 |
| Occurence in plants: |
Vitex strickeri [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Vitex strickeri [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
Serratula wolffii [Asteraceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC(C)CCC1C(OC(O1)(C)C)(C)C2CCC3(C2(CC(C4C3=CC(=O)C5C4(CC(C(C5)O)O)C)O)C)O | 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]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@@H](CCC(C)C)OC(O1)(C)C)O)C)O)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(4R,5R)-2,2,4-trimethyl-5-(3-methylbutyl)-1,3-dioxolan-4-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 12044243 | InChiKey
[ ChemIDPlus: search ] | HNFIAGLFDMBJTE-DISVCFHPSA-N | | InChI | InChI=1S/C30H48O7/c1-16(2)8-9-24-29(7,37-26(3,4)36-24)23-10-11-30(35)18-13-19(31)17-12-20(32)21(33)14-27(17,5)25(18)22(34)15-28(23,30)6/h13,16-17,20-25,32-35H,8-12,14-15H2,1-7H3/t17-,20+,21-,22+,23-,24+,25+,27-,28+,29+,30+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 520 (M)+ (10), 505 (20), 502 (5), 487 (10), 469 (4), 462 (98), 445 (20), 444 (28), 427 (33), 426 (32), 420 (33), 411 10), 409 (20), 402 (13), 379 (20), 361 (17), 299 (12), 281 (7), 266 (33), 185 (100), 142 (58), 127 (83), 114 (33), 109 (33), 84 (60). | | HR-MS | |
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| C5D5N | | 01 | 38.01 | | 02 | 68.15 | | 03 | 68.39 | | 04 | 32.88 | | 05 | 52.46 | | 06 | 203.80 | | 07 | 122.42 | | 08 | 163.80 | | 09 | 42.76 | | 10 | 39.88 | | 11 | 68.71 | | 12 | 43.87 | | 13 | 47.88 | | 14 | 84.21 | | 15 | 31.78 | | 16 | 22.18 | | 17 | 49.81 | | 18 | 18.27 | | 19 | 24.81 | | 20 | 82.01 | | 21 | 22.27 | | 22 | 84.88 | | 23 | 29.38 | | 24 | 36.88 | | 25 | 28.26 | | 26 | 22.45 | | 27 | 22.81 | | Me | 27.14, 27.14 | | O-C-O | 106.92 |
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| C5D5N | | 01-Ha | 2.00 (d, 12) | | 01-He | 3.42 (dd, 5, 12) | | 02-Ha | 4.52 | | 03-He | 4.21 (d, 4) | | 04-Ha | 1.78 (ddd, 4, 14, 14) | | 04-He | 2.03 (dt, 4, 4, 4, 14) | | 05-H | 3.04 (dd, 4, 14) | | 07-H | 6.29 (d, 5) | | 09-Ha | 3.82 | | 11-Ha | 4.57 | | 12-Ha | 2.95 (dd, 12, 12) | | 12-He | 2.57 (dd, 12, 7) | | 15-Ha | 1.95 | | 15-Hb | 2.19 | | 16-Ha | 2.13 | | 16-Hb | 2.23 | | 17-H | 2.79 (dd, 8, 8) | | 18-Me | 1.31 (s ) | | 19-Me | 1.32 (s ) | | 21-Me | 1.08 (s ) | | 22-H | 3.86 | | 23-Ha | 1.55 | | 23-Hb | 1.39 | | 24-Ha | 1.55 | | 24-Hb | 1.50 | | 25-H | 1.46 | | 26-Me | 0.81 (d, 8) | | 27-Me | 0.81 (d, 8) | | Me-ketals | 1.52, 1.46 |
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| M.P. | 246-249 °C (or 287-288 °C) | | [α]D20 | | | IR (Nujol) ν max (cm-1) | 3200 (OH), 1650 (cyclohexenone); ( KBr) 3400-3440(OH), 1675 | | UV (MeOH) λ max (log ε) | 237 (?) |
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| TLC | | | RLCC | solvent system H2O-EtOAc-n-PrOH (6:6:1) | | GLC | | | HPLC | Recycle RP-HPLC, column Asahipack GS-320 (50 x 2 cm i.d.) solvent MeOH, flow-rate 3.5 ml.min-1. |
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Permanent link to this datasheet: AJUGASTERONE C 20,22-MONOACETONIDE
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