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Year of first isolation: |
2005 |
| Formula: | C29H46O7 |
| Molecular weight: | 506 |
| Occurence in plants: |
Serratula coronata [Asteraceae] »  ![Wikipedia: Serratula coronata [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1OC(C(O1)(C)C2CCC3(C2(CC(C4C3=CC(=O)C5C4(CC(C(C5)O)O)C)O)C)O)CCC(C)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]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@@H](CCC(C)C)OC(O1)C)O)C)O)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,11R,13R,14S,17S)-17-[(2R,4R,5R)-2,4-dimethyl-5-(3-methylbutyl)-1,3-dioxolan-4-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 11684847 | InChiKey
[ ChemIDPlus: search ] | IWVNERQHWRVWRA-JILSJDEBSA-N | | InChI | InChI=1S/C29H46O7/c1-15(2)7-8-24-28(6,36-16(3)35-24)23-9-10-29(34)18-12-19(30)17-11-20(31)21(32)13-26(17,4)25(18)22(33)14-27(23,29)5/h12,15-17,20-25,31-34H,7-11,13-14H2,1-6H3/t16-,17+,20-,21+,22-,23+,24-,25-,26+,27-,28-,29-/m1/s1 |
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| HR-MS | | | EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | |
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| D2O | | 01 | 38.8 (t) | | 02 | 68.8 (d) | | 03 | 68.8 (d) | | 04 | ? | | 05 | 52.4 (d) | | 06 | ? | | 07 | 123.4 (d) | | 08 | ? | | 09 | 38.8 (d) | | 10 | 42.3 (s) | | 11 | 69.9 (d) | | 12 | ? | | 13 | 47.9 (s) | | 14 | 86.4 (s) | | 15 | ? | | 16 | ? | | 17 | 51.7 (d) | | 18 | 19.1 (q) | | 19 | 24.8 (q) | | 20 | 87.3 (s) | | 21 | 24.1 (q) | | 22 | ? | | 23 | ? | | 24 | 37.4 (t) | | 25 | 29.1 (d) | | 26 | 23.5 (q) | | 27 | 23.5 (q) | | COMe | 21.7 (q) | | O-C-O | 102.2 (d) |
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| D2O | | 01-Ha | 1.38 (m) | | 01-He | 2.48 (dd, 13.5, 4.0) | | 02-Ha | 4.09 (m) | | 03-He | 4.09 (m) | | 04-Ha | 1.74 (t) | | 04-He | 1.74 (t) | | 05-H | 2.32 (m) | | 07-H | 5.98 (d, 2.5) | | 09-H | 3.11 (br d, 8.5) | | 11-Ha | 4.20 (m, w1/2 = 27) | | 12-Ha | 2.02* (m) | | 12-He | 2.18* (m) | | 15-Ha | 1.67 (m) | | 15-Hb | 2.05 (m) | | 16-Ha | 1.95** (m) | | 16-Hb | 1.80** (m) | | 17-H | 2.31 (m) | | 18-Me | 0.84 (s) | | 19-Me | 1.09 (s) | | 21-Me | 1.24 (s) | | 22-H | 3.83 (m, w1/2 = 18) | | 23-Ha | 1.56 (m) | | 23-Hb | 1.36 (m) | | 24-Ha | 1.53 (m) | | 24-Hb | 1.30 (m) | | 25-H | 1.60 (m) | | 26-Me | 0.90 (d, 6.9) | | 27-Me | 0.90 (d, 6.9) | | O-C(Me)-O | 1.38 (d, 5.0) | | O-CH-O | 5.15 (q, 5.0) |
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| M.P. | ? °C ; | | [α]D20 | ? ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | ? (?) ; |
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| HPLC | NP-HPLC Zorbax-SIL (250 x 9.4 mm) solvent dichloromethane-isopropanol-water (125:15:1), flow-rate 4 ml/min (Ret 22.3 min); Kromasil (250x 4.6 mm), solvent cyclohexane-isopropanol-water (100:30:2), flow-rate 1 ml/min (Ret 25.1 min). | | HPTLC | | | TLC | |
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Permanent link to this datasheet: AJUGASTERONE C 20,22-ETHYLIDENE ACETAL
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