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Year of first isolation: |
1987 |
| Formula: | C30H48O7 |
| Molecular weight: | 520 |
| Occurence in plants: |
Rhaponticum carthamoides [Asteraceae] »  ![Wikipedia: Rhaponticum carthamoides [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1(OC2CC3C(=O)C=C4C(C3(CC2O1)C)CCC5(C4(CCC5C(C)(C(CCC(C)(C)O)O)O)O)C)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@@H]3[C@H]1OC(O3)(C)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | (1R,2R,4S,8R,10R,14S,17S,18R)-14-hydroxy-2,6,6,18-tetramethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one | | CAS-RN | | | PubChem CID | 11060392 | InChiKey
[ ChemIDPlus: search ] | OWTQJKQVBMPILJ-VUYJMULXSA-N | | InChI | InChI=1S/C30H48O7/c1-25(2,33)11-10-24(32)29(7,34)23-9-13-30(35)18-14-20(31)19-15-21-22(37-26(3,4)36-21)16-27(19,5)17(18)8-12-28(23,30)6/h14,17,19,21-24,32-35H,8-13,15-16H2,1-7H3/t17-,19-,21+,22-,23-,24+,27+,28+,29+,30+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 520 (M)+ (1), 505 (7), 502 (2), 487 (3), 484 (2), 469 (5), 466 (4), 451 (4), 403 (72), 385 (100), 371 (7), 368 (6), 360 (7), 345 (10), 327 (36), 309 (9),269 (13), 143 (12), 99 (36), 81 (24). | | HR-MS | |
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| CD3OD | | 01 | 38.7 | | 02 | 73.5 | | 03 | 73.2 | | 04 | 27.7 | | 05 | 52.5 | | 06 | 205.6 | | 07 | 121.8 | | 08 | 167.2 | | 09 | 35.7 | | 10 | 38.9 | | 11 | 21.6 | | 12 | 32.5 | | 13 | * | | 14 | 85.2 | | 15 | 31.7 | | 16 | 21.5 | | 17 | 50.5 | | 18 | 18.0 | | 19 | 24.0 | | 20 | 77.9 | | 21 | 21.0 | | 22 | 78.4 | | 23 | 27.3 | | 24 | 42.9 | | 25 | 71.3 | | 26 | 29.7 | | 27 | 28.9 | | 28 | | | 29 | | | iPr- (2,3) | 109.5, 28.8 26.6 |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.99 | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.04 (s ) | | 19-Me | 0.88 (s ) | | 21-Me | 1.42 (s ) | | 22-H | | | 23-H | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.23 (s ) | | 27-Me | 1.23 (s ) | | Other | 1.23 and 1.42 |
| Me2CO-d6 | | 01-Ha | | | 01-He | | | 02-H | 4.23 (m ) | | 02-Ha | | | 03-H | 4.24 (m ) | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.70 (d, 2.7) | | 09-H | 2.96 (ddd, 11.6, 7.0, 2.7) | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.45 (t, 9.0) | | 18-Me | 0.91 (s ) | | 19-Me | 0.96 (s ) | | 21-Me | 1.19 (s ) | | 22-H | 3.36 (br d, 10.3, <2) | | 23-H | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.18 (s ) | | 27-Me | 1.17 (s ) | | iPr- (2,3) | 1.42 (s ), 1.26 (s ) | | Other | |
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| M.P. | 232-233 °C | | [α]D20 | 56.4 ? 2 ° (c 0.9 ; MeOH) | | IR (KBr) ν max (cm-1) | 3460-3500 (OH), 1643 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 244 (4.08) |
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Drosophila melanogaster BII cell assay: EC50 = 1.5 x 10-7M |
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| First isolation | BALTAYEV, U.A. et al. (1987) Khim. Prir. Soedin. 681-684 |
 | | General | PIS, J. et al. (1994) Phytochemistry 37, 707-711 |
| | 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: 20-HYDROXYECDYSONE 2,3-MONOACETONIDE
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