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Year of first isolation: |
1999 |
| Formula: | C29H44O9 |
| Molecular weight: | 536 |
| 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 | CC1(C(CC(=O)O1)(CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)O)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](CC1(C(OC(=O)C1)(C)C)O)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](C[C@]1(CC(=O)OC1(C)C)O)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](C[C@@]1(CC(=O)OC1(C)C)O)O)O)O)C)C »
| | IUPAC Name | 4-[(2R,3S)-2,3-dihydroxy-3-[(2S,3R,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]butyl]-4-hydroxy-5,5-dimethyloxolan-2-one | | CAS-RN | | | PubChem CID | 11466802 | InChiKey
[ ChemIDPlus: search ] | LMGYKASFFZVSND-SJKUBCSYSA-N | | InChI | InChI=1S/C29H44O9/c1-24(2)28(36,14-23(34)38-24)13-22(33)27(5,35)21-7-9-29(37)16-10-18(30)17-11-19(31)20(32)12-25(17,3)15(16)6-8-26(21,29)4/h10,15,17,19-22,31-33,35-37H,6-9,11-14H2,1-5H3/t15?,17?,19-,20+,21+,22-,25-,26-,27+,28?,29-/m1/s1 |
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| EI-MS m/z (relative intensity %) | 500 (8), 482 (20), 464 (20), 446(37), 421 (18), 355 (11), 343 (17), 327 (39), 315 (17), 301 (47), 282 (32), 267 (46), 255 (29), 250 (37), 239 (36), 213 (60), 199 (39), 181 (73), 167 (66), 139 (74), 129 (72), 111 (70), 95 (100), 81 (100). | | FAB-MS m/z (relative intensity %) | 541 (85) [M+Na-H2O]+, 519.30307 (64) [M+H-H2O]+ for C29H43O8 required 519.29579, 501 (96), 363 (10), 303 (52), 279 (34), 199 (100) |
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| CD3OD | | 01 | 37.37 | | 02 | 68.76 | | 03 | 68.52 | | 04 | 32.91 | | 05 | 51.77 | | 06 | 206.58 | | 07 | 122.15 | | 08 | 168.10 | | 09 | 35.17 | | 10 | 39.17 | | 11 | 21.60 | | 12 | 32.44 | | 13 | * | | 14 | 85.05 | | 15 | 32.10 | | 16 | 24.36 | | 17 | 51.11 | | 18 | 18.09 | | 19 | 24.43 | | 20 | 81.21 | | 21 | 21.48 | | 22 | 90.78 ** | | 23 | 39.60 | | 24 | 91.79 ** | | 25 | 91.84 ** | | 26 | 24.73 | | 27 | 27.13 | | 28 | 44.35 | | 29 | 178.29 |
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| CD3OD | | 01-Ha | 1.78 (dd, 13.4, 4.5) | | 01-He | 1.42 (dd, 13.4, 12.2) | | 02-H | 3.83 (ddd, 11.8, 4.4, 3.0) | | 03-H | 3.94 (q, ~2.8) | | 04-Ha | 1.78 (td, 14.0, 12.5, 2.8) | | 04-He | 1.49 (ddd, 14.0, 4.8, 2.8) | | 05-H | 2.37 (bdd, 12.5, 4.8) | | 07-H | 5.82 (bd, 2.6) | | 09-H | 3.15 (ddd, 11.4, 6.8, 2.6) | | 11-Ha | 1.79 | | 11-He | 1.66 | | 12-Ha | 2.14 | | 12-He | 1.59 | | 15-Ha | 1.95 | | 15-Hb | 1.85 | | 16-Ha | 2.16 | | 16-Hb | 1.90 | | 17-H | 2.70 dd (9.6, 8.0) | | 18-Me | 0.80 (s) | | 19-Me | 0.95 (s) | | 21-Me | 1.22 (s) | | 22-H | 3.97 dd (4.8, 0.8) | | 23-Ha | 2.43 (dd, 13.6, 4.8) | | 23-Hb | 1.82 (dd, 13.6, 0.8) | | 26-Me | 1.36 (s) | | 27-Me | 1.39 (s) | | 28-Ha | 2.97 (d, 17.7) | | 28-Hb | 2.91 (d, 17.7) |
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| M.P. | 275-283 °C (decomp.) | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3387 (OH), 1770 (gama-lactone), 1650 (CO) | | UV (EtOH) λ max (log ε) | |
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| NP-HPLC | column Silasorb 600 (4 x 250 mm), solvent n-hexane ? EtOH ? H2O (812:180:8), flow rate 0.8 ml.min-1. Ret 72,4 min (20E 50.7 min). | | RP-HPLC | column Separon SIX C18 (4 x 250 mm), solvent MeOH - H2O, linear gradient 10 to 70% MeOH in 50 min, flow rate 0.6 ml.min-1. Ret 46,5 min (20E 34.2 min). | | TLC | | | GLC | | | HPLC | |
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| General | VOKÁČ, K. et al. (1999) 18th Conference on Isoprenoids, Prachatice, Chemické Listy, Symposia 93, p. 60 |
 | | Bioactivities | DINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 |
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Permanent link to this datasheet: 24-HYDROXY-24,28-DIHYDROCARTHAMOSTERONE
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