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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(CC(C(C)(C)O)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](C[C@H](C(C)(C)O)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,5R)-2,3,5,6-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 | 16755634 | InChiKey
[ ChemIDPlus: search ] | JZLJYAKQIWKLJN-GZOLVMJQSA-N | | InChI | InChI=1S/C27H44O9/c1-23(2,34)20(32)10-21(33)26(5,35)19-6-7-27(36)14-9-15(28)13-8-16(29)17(30)11-24(13,3)22(14)18(31)12-25(19,27)4/h9,13,16-22,29-36H,6-8,10-12H2,1-5H3/t13-,16+,17-,18+,19-,20+,21+,22+,24-,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | FAB-HR-MS | (negative mode): 511.2912, [M-H]- (calc. 511.2907 for C27H44O9 -H) |
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| C5D5N | | 01 | 39.64 | | 02 | 68.19 | | 03 | 67.94 | | 04 | 32.61 | | 05 | 52.25 | | 06 | 203.73 | | 07 | 122.00 | | 08 | 164.11 | | 09 | 42.54 | | 10 | 39.31 | | 11 | 68.63 | | 12 | 43.96 | | 13 | 48.00 | | 14 | 84.06 | | 15 | 31.64 | | 16 | 21.18 | | 17 | 49.73 | | 18 | 18.72 | | 19 | 24.65 | | 20 | 76.62 | | 21 | 21.47 | | 22 | 73.53* | | 23 | 35.00 | | 24 | 75.73* | | 25 | 72.40 | | 26 | 25.85 | | 27 | 25.92 | | Note | * assignments can be reversed, |
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| C5D5N | | 01-Ha ? | 3.43 (dd, 12.5, 3.8) | | 01-He | | | 02-Ha | 4.57 (m) | | 03-He | 4.20 (br, s) | | 04-Ha | | | 04-He | | | 05-H | 3.00 (dd, 12.7, 3.2) | | 07-H | 6.25 (d, ca. 2) | | 09-H | 3.84 (br, d, 7) | | 11-Ha | 4.60 (m) | | 12-Ha | 3.04* | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.16 (t, 9.1)* | | 18-Me | 1.26 (s) | | 19-Me | 1.29 (s) | | 21-Me | 1.61 (s) | | 22-H | 4.50 (br, d, 8.6)** | | 23-Ha | | | 23-Hb | | | 24-H | 4.35 (br, d, 8.8)** | | 26-Me | 1.45 (s) | | 27-Me | 1.45 (s) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3408, 2967, 1654, 1384, 1052 | | 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 26.6 min. | | NP-HPLC | column Hypersil Si, 5 ?m, 250x4.6 mm; solvent CHCl3-MeOH (90:10), flow-rate 1.2 ml.min-1, Ret 13.0 min. |
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Permanent link to this datasheet: (24R)-11α,20,24-TRIHYDROXYECDYSONE
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