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Year of first isolation: |
2008 |
| Formula: | C29H48O8 |
| Molecular weight: | 524 |
| 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 | CCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(C(C(C(C4)O)O)O)C)C)O)O)O)C(C)(C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | [C@@H]1([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](CC(C(C)(C)O)CC)O)O)O)C)C)O » 
[C@@H]1([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](C[C@H](C(C)(C)O)CC)O)O)O)C)C)O »
[C@@H]1([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](C[C@@H](C(C)(C)O)CC)O)O)O)C)C)O »
| | IUPAC Name | (1S,2R,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R,5R)-5-ethyl-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,14-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 | 101851586 | InChiKey
[ ChemIDPlus: search ] | KWOLRPNEMKAFDT-SVPRUFJPSA-N | | InChI | InChI=1S/C29H48O8/c1-7-15(25(2,3)35)12-22(32)28(6,36)21-9-11-29(37)17-13-19(30)18-14-20(31)23(33)24(34)27(18,5)16(17)8-10-26(21,29)4/h13,15-16,18,20-24,31-37H,7-12,14H2,1-6H3/t15-,16+,18+,20-,21+,22-,23-,24-,26-,27-,28-,29-/m1/s1 |
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| HR-ESI-MS | 547.3251 [M+Na]+ (calculated for C29H48O8Na : 547.3247) | | ESI-MS/MS m/z | 525 [M+H]+, 507 [M+H-H20]+, 489 [M+H-2H20]+, 471 [M+H-3H2O]+, 453 [M+H-4H2O]+, 387, 363, 345, 319, 171, 127. |
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| CD3OD | | 01 | 76.45 | | 02 | 68.47 | | 03 | 71.00 | | 04 | 33.52 | | 05 | 46.78 | | 06 | 205.55 | | 07 | 122.16 | | 08 | 167.23 | | 09 | 35.63 | | 10 | 43.80 | | 11 | 21.91 | | 12 | 32.49 | | 13 | ~49.0** | | 14 | 85.04 | | 15 | 31.82 | | 16 | 21.51 | | 17 | 50.45 | | 18 | 18.04 | | 19 | 20.03 | | 20 | 77.98 | | 21 | 20.95 | | 22 | 77.22 | | 23 | 33.04 | | 24 | 50.29 | | 25 | 74.12 | | 26 | 25.60 | | 27 | 29.09 | | 28 | 25.97 | | 29 | 14.35 |
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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 | ~1.80 | | 04-He | ~1.80 | | 05-H | 2.61 (dd, 12.5, 4.5) | | 07-H | 5.83 (d, 2.5) | | 09-H | 3.08 (bt) | | 11-Ha | 1.70 | | 11-He | 1.78 | | 12-Ha | 2.10 (td, 13, 13, 5) | | 12-He | 1.87 | | 15-Ha | 1.99 | | 15-Hb | 1.62 | | 16-Ha | 1.76 | | 16-Hb | 2.03 | | 17-H | 2.41 (dd, 9.5, 8.5) | | 18-Me | 0.910 (s) | | 19-Me | 1.079 (s) | | 21-Me | 1.196 (s) | | 22-H | 3.41 (dd, 10.8, 1.7) | | 23-Ha | 1.56 | | 23-Hb | 1.41 | | 24-H | 1.47 | | 26-H | 1.105 (s) | | 27-Me | 1.215 (s) | | 28-Ha | 1.57 | | 28-Hb | 1.15 | | 29-Me | 1.015 (t, 7.4, 7.4) |
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| M.P. | °C ; | | [α]D20 | + 64.0 ° (c 0.075; EtOH) | | IR (KBr) ν max (cm-1) | 3409 (OH), 1654 (C=O), 1056 (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: 1β-HYDROXYMAKISTERONE C
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