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Year of first isolation: |
1981 |
| Formula: | C27H44O5 |
| Molecular weight: | 448 |
| Occurence in plants: |
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| Occurence in animals: |
Bombyx mori [Bombycidae] »  ![Wikipedia: Bombyx mori [Bombycidae]](/images/wikipedia.png)
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| Canonical SMILES | CC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(C)(CCCC(C)(C)O)O)O)C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(CCCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (3R,5R,10R,13R,14S,17R)-17-(2,6-dihydroxy-6-methylheptan-2-yl)-3,14-dihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 129637605 | InChiKey
[ ChemIDPlus: search ] | NGORFCHZENUGIY-UOMGQMBVSA-N | | InChI | InChI=1S/C27H44O5/c1-23(2,30)10-6-11-26(5,31)22-9-14-27(32)19-16-21(29)20-15-17(28)7-12-24(20,3)18(19)8-13-25(22,27)4/h16-18,20,22,28,30-32H,6-15H2,1-5H3/t17-,18?,20+,22-,24-,25-,26?,27-/m1/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 448 (M)+, 430 (M - 18)+, 415 (M - 18 - 15)+, 412, 397, 394, 379, 361, 347 (M - C22-C27)+, 329, 311, 304 (M - C20-C27)+, 286, 271, 253, 234, 145 (C20-C27)+, 127, 109, 59, 41 | | HR-MS | 448.3198 (M)+ |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| CDCl3 | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | 5.14 (m ) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.90 (s br ) | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.86 (s ) | | 19-Me | 1.00 (s ) | | 21-Me | 1,24 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1,26 (s ) | | 27-Me | 1,26 (s ) | | Me-CO- | 2.08 (s,3H) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 245 (4.079) |
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| HPTLC | | | TLC | silica Rf 0.46 (solvent CHCl3-96% EtOH) (2DE 0.54; E 0.32) | | GLC | | | HPLC | 1- Retention time 9.2 min [ Zorbax-Sil 150 mm x 4.6 mm i.d., solvent CH2Cl2-MeOH 93:7 v/v, flow-rate 1 ml.min-1 ] (2DE : 8.5 min; E : 14.6 min) 2-Retention time 21.0 min [ Wakogel ODS-10K 500 mm x 4.6 mm i.d., solvent MeOH-H2O 3:2 v/v, flow-rate 1 ml.min-1 ] (2DE : 19.1 min; E : 9.9 min) |
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Drosophila melanogaster BII cell assay: EC50 = ca. 5.0 x 10-5M |
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Permanent link to this datasheet: 2,22-DIDEOXY-20-HYDROXYECDYSONE
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