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Year of first isolation: |
2002 |
| Formula: | C27H42O8 |
| Molecular weight: | 494 |
| Occurence in plants: |
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| Occurence in animals: |
Chironomus tentans cell line [Diptera] »  ![Wikipedia: Chironomus tentans cell line [Diptera]](/images/wikipedia.png)
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| Canonical SMILES | | 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]1O[C@H]([C@](CC1)(O)C)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-((R)-1-((2S,5S,6R)-5,6-dihydroxy-5-methyltetrahydro-2H-pyran-2-yl)-1-hydroxyethyl)-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | JIILRQPUAKUWFJ-BXDBVBPTSA-N | | InChI | InChI=1S/C27H42O8/c1-23-13-19(30)18(29)12-16(23)17(28)11-15-14(23)5-8-24(2)20(6-10-27(15,24)34)26(4,33)21-7-9-25(3,32)22(31)35-21/h11,14,16,18-22,29-34H,5-10,12-13H2,1-4H3/t14-,16-,18+,19-,20-,21-,22+,23+,24+,25-,26+,27+/m0/s1 |
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| HR-MS | | | APCI-MS (negative mode) m/z | 493 (M-1) (base peak), 476 (M-18) | | EI-MS m/z (relative intensity %) | |
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| D2O | | 01 | | | 02 | 67.9 | | 03 | 67.8 | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | 82.0 | | 23 | | | 24 | | | 25 | | | 26 | 99.5 | | 27 | 17.8 (trans), 23.7 (cis) |
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| D2O | | 01-Ha | | | 01-He | | | 02-Ha | 4.01 | | 03-He | 4.09 | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | | | 09-H | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.84 | | 19-Me | 1.02 | | 21-Me | 1.29 | | 22-H | 3.54 (trans), 3.86 (cis) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-H | 4.60 (m) | | 27-Me | 1.23 (trans), 1.32 (cis) |
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| M.P. | °C ; | | [α]D20 | ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (MeOH) λ max (log ε) | 248 nmp () ; |
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| HPLC | RP-HPLC Nucleosil C18 5 ?m (250 x 4.6 mm), isocratic MeOH-water (33:67) for 60 min, then gradient to 62:38 over 3 min then 62:38 isocratic, retention time isomers elute at 49 and 69 min (20E 42 min, 2026E 19 min). | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 20,26-DIHYDROXYECDYSONE 22,26-HEMIACETAL
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