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Year of first isolation: |
1994 |
| Formula: | C33H52O7 |
| Molecular weight: | 560 |
| 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(OC2CC3C(=O)C=C4C(C3(CC2O1)C)CCC5(C4(CCC5C6(C(OC(O6)(C)C)CCC(C)(C)O)C)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@]1(C)[C@@H](CCC(C)(C)O)OC(O1)(C)C)O)C)C » 
| | IUPAC Name | (1R,2R,4S,8R,10R,14S,17S,18R)-14-hydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one | | CAS-RN | 22798-98-7 | | PubChem CID | 11082278 | InChiKey
[ ChemIDPlus: search ] | WXFMGCVRGSIXOB-APTIWFLNSA-N | | InChI | InChI=1S/C33H52O7/c1-27(2,35)13-12-26-32(9,40-29(5,6)39-26)25-11-15-33(36)20-16-22(34)21-17-23-24(38-28(3,4)37-23)18-30(21,7)19(20)10-14-31(25,33)8/h16,19,21,23-26,35-36H,10-15,17-18H2,1-9H3/t19-,21-,23+,24-,25-,26+,30+,31+,32+,33+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 560 (1), 545 (12), 527 (10), 509 (5), 403 (100), 385 (25), 341 (20) | | FAB-MS m/z | 583 (M+Na)+ (20), 561 (M+H)+ (20), 543 (25), 485 (M+H-H2O-acetone) (28), 427 (10) |
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| CD3OD | | 01 | 38.72 | | 02 | 73.50 | | 03 | 73.13 | | 04 | 27.69 | | 05 | 52.47 | | 06 | 205.59 | | 07 | 121.80 | | 08 | 166.88 | | 09 | 35.77 | | 10 | 38.84 | | 11 | 21.60 | | 12 | 32.30 | | 13 | * | | 14 | 85.23 | | 15 | 31.60 | | 16 | 22.44 | | 17 | 50.48 | | 18 | 17.67 | | 19 | 24.01 | | 20 | 85.83 | | 21 | 22.60 | | 22 | 83.30 | | 23 | 24.70 | | 24 | 42.21 | | 25 | 71.10 | | 26 | 29.50 | | 27 | 29.35 | | iPr- (2,3) | 109.45, 28.82, 26.64 | | iPr- (20,22) | 108.00, 28.96, 27.18 |
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| CD3COCD3 | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.23 (m ) | | 03-He | 4.25 (m ) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.71 (d, 2.7) | | 09-Ha | 2.96 (ddd, 12.0, 7.0, 2.7) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.37 (dd, 9.0, 8.5) | | 18-Me | 0.825 (s ) | | 19-Me | 0.952 (s ) | | 21-Me | 1.182 (s ) | | 22-H | 3.68 (dd, 7.0, 5.5) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.176 (s ) | | 27-Me | 1.167 (s ) | | iPr- (2,3) | 1.423 (s), 1.254 (s) | | iPr- 20,22 | 1.361 (s), 1.297 (s) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3449 (OH), 1664 (=C=O), 1381, 1373 (gem-diMe), 1169, 1059 | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | NP-HPLC | (Separon SGX silica 7 ?m) (CH2Cl2-MeOH-H2O 88:11:1) |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 2,3;20,22-DIACETONIDE
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