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Year of first isolation: |
2000 |
| Formula: | C27H44O9 |
| Molecular weight: | 512 |
| Occurence in plants: |
Vitex canescens [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Vitex canescens [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CC(C3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(CO)O)O)O)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]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(CO)(C)O)O)O)O)C)O)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(CO)(C)O)O)O)O)C)O)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(CO)(C)O)O)O)O)C)O)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 102237690 | InChiKey
[ ChemIDPlus: search ] | KLDBEDBIBHZKCM-ZKJAEQJOSA-N | | InChI | InChI=1S/C27H44O9/c1-23(34,13-28)7-6-21(33)26(4,35)20-5-8-27(36)15-10-16(29)14-9-17(30)18(31)11-24(14,2)22(15)19(32)12-25(20,27)3/h10,14,17-22,28,30-36H,5-9,11-13H2,1-4H3/t14-,17+,18-,19+,20-,21+,22+,23?,24-,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | HR-FAB-MS | (negative mode): 511.2906 and 511.2908 for the two epimers, respectivelly, [M-H]- (calc. 511.2907 for C27H44O9 -H) |
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| C5D5N | | 01 | 39.65 39.64 | | 02 | 68.20 68.20 | | 03 | 67.94 67.94 | | 04 | 32.64 32.66 | | 05 | 52.26 52.26 | | 06 | 203.74 203.76 | | 07 | 122.02 122.01 | | 08 | 164.07 164.09 | | 09 | 42.53 42.53 | | 10 | 39.30 39.30 | | 11 | 68.62 68.62 | | 12 | 43.93 43.93 | | 13 | 47.96 47.96 | | 14 | 84.01 84.01 | | 15 | 31.65 31.65 | | 16 | 21.40 21.41 | | 17 | 49.78 49.78 | | 18 | 18.68 18.68 | | 19 | 24.65 24.65 | | 20 | 76.62 76.61 | | 21 | 21.29 21.32 | | 22 | 77.29 77.43 | | 23 | 26.57 26.51 | | 24 | 37.35 37.31 | | 25 | 72.41 72.37 | | 26 | 70.63 70.44 | | 27 | 24.32 24.52 |
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| C5D5N | | 01-Ha ? | 3.43 (dd, 12.4, 3.5) 3.44 (dd, 12.5, 3.5) | | 01-He | | | 02-Ha | 4.58 (m) 4.58 (m) | | 03-He | 4.20 (br, s) 4.21 (br, s) | | 04-Ha | | | 04-He | | | 05-H | 3.00 3.00 | | 07-H | 6.28 (d, ca. 2) 6.28 (br, s) | | 09-H | 3.85-3.89 3.85-3.89 | | 11-Ha | 4.58 (m) 4.58 (m) | | 12-Ha | 3.02 3.02 | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.09 (t, 9.1) 3.09 (t, 8.9) | | 18-Me | 1.24 (s) 1.24 (s) | | 19-Me | 1.30 (s) 1.30 (s) | | 21-Me | 1.56 (s) 1.56 (s) | | 22-H | 3.85-3.89 3.85-3.89 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-H (2) | 3.85-3.89 3.85-3.89 | | 26-Me | ? ? | | 27-Me | 1.45 (s) 1.45 (s) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3448, 2952, 1660, 1385, 10535; 3448, 2927, 1660, 1385, 1053 | | UV (EtOH) λ max (log ε) | |
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| TLC | | | GLC | | | RP-HPLC | column ?Bondapak C18, 10 ?m, 300x3.9 mm, solvent MeOH-H2O (18:82), flow-rate 1.0 ml.min-1, Ret 34.4 and 40.8 min. | | NP-HPLC | column Hypersil Si, 5 ?m, 250x4.6 mm; solvent CHCl3-MeOH (90:10), flow-rate 1.2 ml.min-1, Ret 16.4 min (for both epimers). |
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Permanent link to this datasheet: 11α,20,26-TRIHYDROXYECDYSONE
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