|
|
|
|
Year of first isolation: |
2008 |
| Formula: | C29H44O7 |
| Molecular weight: | 508 |
| Occurence in plants: |
Leuzea carthamoides [Asteraceae] »  ![Wikipedia: Leuzea carthamoides [Asteraceae]](/images/wikipedia.png)
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CC(C(CCC(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)C(C)(C)O)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]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCC(C(C)(C)O)C(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)(CC[C@H](C(C)(C)O)C(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)(CC[C@@H](C(C)(C)O)C(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)(CC[C@H](C(C)(C)O)C(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)(CC[C@@H](C(C)(C)O)C(C)O)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2S,5S)-2,6-dihydroxy-5-(1-hydroxyethyl)-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101851585 | InChiKey
[ ChemIDPlus: search ] | IUHZXHYYRUEMNW-MWRLSSAHSA-N | | InChI | InChI=1S/C29H48O7/c1-16(30)17(25(2,3)34)8-11-28(6,35)24-9-12-29(36)19-13-21(31)20-14-22(32)23(33)15-26(20,4)18(19)7-10-27(24,29)5/h13,16-18,20,22-24,30,32-36H,7-12,14-15H2,1-6H3/t16?,17-,18-,20-,22+,23-,24-,26+,27+,28-,29+/m0/s1 |
| |
| ESI-MS/MS m/z | 509 [M+H]+, 491 [M+H-H20]+, 473 [M+H-2H20]+, 455 [M+H-3H2O]+, 437 [M+H-4H2O]+, 447 [M+H-C3H8O]+, 429 [M+H-H2O-C3H8O]+, 411 [M+H-2H2O-C3H8O]+, 171, 153, 135. | | HR-ESI-MS m/z | 531.3291 [M+Na]+ (calculated for C29H44O7Na : 531.3298) |
|
|
| CD3OD | | 01 | 37.39 | | 02 | 68.72 | | 03 | 68.52 | | 04 | ~33.00 | | 05 | 51.81 | | 06 | ~206.30 | | 07 | 122.12 | | 08 | 167.97 | | 09 | ~34.80 | | 10 | 39.27 | | 11 | ~21.60 | | 12 | 32.46 | | 13 | 49.0** | | 14 | 85.53 | | 15 | 31.60 | | 16 | 22.02 | | 17 | 53.11 | | 18 | 18.10 | | 19 | 24.40 | | 20 | 75.85 | | 21 | 26.28 | | 22 | 46.48 | | 23 | 24.61 | | 24 | 56.44 | | 25 | 76.12 | | 26 | 24.82 | | 27 | 29.64 | | 28 | 71.69 | | 29 | 22.64 |
|
| CD3OD | | 01-Ha | 1.43 | | 01-He | 1.78 | | 02-Ha | 3.83 (ddd, 12.0, 4.2, 3.0) | | 03-He | 3.95 (q, 3, 3, 3) | | 04-Ha | ~1.70 | | 04-He | ~1.70 | | 05-H | 2.38 (dd, 12.6, 4.4) | | 07-H | 5.81 (d, 2.5) | | 09-Ha | 3.15 (ddd, 11.5, 7, 2.5) | | 11-Ha | 1.69 | | 11-He | 1.80 | | 12-Ha | 2.11 (td, 13, 13, 5) | | 12-He | 1.83 | | 15-Ha | 1.95 | | 15-Hb | 1.62 | | 16-Ha | 1.86 | | 16-Hb | 1.92 | | 17-H | 2.27 (dd, 9.8, 8.2) | | 18-Me | 0.854 (s) | | 19-Me | 0.963 (s) | | 21-Me | 1.264 (s) | | 22-Ha | 1.68 | | 22-Hb | 1.47 | | 23-Ha | 1.28 | | 23-Hb | 1.06 | | 24-H | 1.23 | | 26-Me | 1.233 (s) | | 27-Me | 1.247 (s) | | 28-Ha | 3.90 (dq, 9.0, 6.2, 6.2, 6.2) | | 29-Me | 1.234 (s) |
|
| |
| M.P. | °C ; | | [α]D20 | + 34.9 ° (c 0.16; EtOH) | | IR (KBr) ν max (cm-1) | 3400 (OH), 1652 (C=O), 1060 (C-O) | | UV (MeOH) λ max (log ε) | |
| |
| 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 | |
| |
| |
| |
Permanent link to this datasheet: 22-DEOXY-28-HYDROXYMAKISTERONE C
|
|
