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Year of first isolation: |
2005 |
| Formula: | C29H46O8 |
| Molecular weight: | 522 |
| 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 | CC(CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)COC(=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)([C@@H](CCC(C)COC(=O)C)O)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)([C@@H](CCC(C)COC(=O)C)O)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)([C@@H](CCC(C)COC(=O)C)O)O)O)C)C »
| | IUPAC Name | [(2S,5R,6R)-5,6-dihydroxy-2-methyl-6-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptyl] acetate | | CAS-RN | | | PubChem CID | 11591734 | InChiKey
[ ChemIDPlus: search ] | FARFYWFUAMLBAX-CZDBYVCJSA-N | | InChI | InChI=1S/C29H46O8/c1-16(15-37-17(2)30)6-7-25(34)28(5,35)24-9-11-29(36)19-12-21(31)20-13-22(32)23(33)14-26(20,3)18(19)8-10-27(24,29)4/h12,16,18,20,22-25,32-36H,6-11,13-15H2,1-5H3/t16-,18-,20-,22+,23-,24-,25+,26+,27+,28+,29+/m0/s1 |
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| HR-MS | | | EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | 540 [M + H + NH3]+, 522 [M]+, 505, 498, 480, 464, 434, 416, 352, 308, 291, 220, 176, 153, 116. |
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| D2O | | 01 | 36.6 (t) | | 02 | 68.5 (d) | | 03 | 68.2 (d) | | 04 | 32.4 (t) | | 05 | 51.7 (d) | | 06 | 209.8 (s) | | 07 | 122.1 (d) | | 08 | ? | | 09 | 34.9 (d) | | 10 | 39.3 (s) | | 11 | 21.3 (t) | | 12 | 32.0 (t) | | 13 | 48.3 (s) | | 14 | 86.1 (s) | | 15 | 31.5 (t) | | 16 | 21.3 (t) | | 17 | 50.3 (d) | | 18 | 18.0 (q) | | 19 | 24.2 (q) | | 20 | 79.3 (s) | | 21 | 20.7 (q) | | 22 | 78.2 (d) | | 23 | 29.1 (t) | | 24 | 31.5 (t) | | 25 | 33.2 (d) | | 26 | 71.2 (t) | | 27 | 17.3 (q) | | CH3 | 21.7 (q) | | CO | ? |
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| D2O | | 01-Ha | 1.38 (t, 13.4) | | 01-He | 1.88 (m) | | 02-Ha | 3.99 (m, w1/2 = 22) | | 03-He | 4.07 (m, w1/2 = 8) | | 04-Ha | 1.75 (t) | | 04-He | 1.75 (t) | | 05-H | 2.34 (t) | | 07-H | 5.97 (d, 2.0) | | 09-H | 3.11 (m, w1/2 = 22) | | 11-Ha | 1.73 (m) | | 11-He | 1.86 (m) | | 12-Ha | 1.95 (m) | | 12-He | 1.75 (m) | | 15-Ha | 1.65 (m) | | 15-Hb | 2.05 (m) | | 16-Ha | 1.75* (m) | | 16-Hb | 1.86* (m) | | 17-H | 2.31 (t, 9.0) | | 18-Me | 0.86 (s) | | 19-Me | 1.00 (s) | | 21-Me | 1.22 (s) | | 22-H | 3.43 (dd, 10.0, 1.0) | | 23-Ha | 1.24 (m) | | 23-Hb | 1.65 (m) | | 24-Ha | 1.27 (m) | | 24-Hb | 1.65 (m) | | 25-H | 1.87 (m) | | 26-Ha | 4.05 (dd, 11.0, 6.0) | | 26-Hb | 3.95 (dd, 11.0, 6.5) | | 27-Me | 0.96 (d, 6.9) |
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| M.P. | ? °C ; | | [α]D20 | ? ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (MeOH) λ max (log ε) | 242 nm (?) ; |
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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 19.0 min); Kromasil (250x 4.6 mm), solvent cyclohexane-isopropanol-water (100:30:2), flow-rate 1 ml/min (Ret 4.5 min).
RP-HPLC Spherisorb 5ODS2, solvent methanol-water (60:40), flow-rate 1 ml/min (Ret 10.8 min). | | HPTLC | | | TLC | |
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Permanent link to this datasheet: INOKOSTERONE 26-ACETATE
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