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Year of first isolation: |
1992 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Vitex strickeri [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Vitex strickeri [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)C(CCC(C)(C)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@H](C)[C@@H](CCC(C)(C)O)O)O)C)O)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,11R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101618910 | InChiKey
[ ChemIDPlus: search ] | DXGPJKXCWRHUMH-VJQXMUGRSA-N | | InChI | InChI=1S/C27H44O7/c1-14(18(28)7-8-24(2,3)33)15-6-9-27(34)17-11-19(29)16-10-20(30)21(31)12-25(16,4)23(17)22(32)13-26(15,27)5/h11,14-16,18,20-23,28,30-34H,6-10,12-13H2,1-5H3/t14-,15+,16-,18+,20+,21-,22+,23+,25-,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 481 [M+1]+ |
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| C5D5N | | 01 | 39.54 | | 02 | 68.39 | | 03 | 68.14 | | 04 | 32.88 | | 05 | 52.49 | | 06 | 204.00 | | 07 | 122.17 | | 08 | 163.80 | | 09 | 42.88 | | 10 | 39.86 | | 11 | 68.77 | | 12 | 42.93 | | 13 | 47.53 | | 14 | 83.87 | | 15 | 32.11 | | 16 | 26.67 | | 17 | 48.26 | | 18 | 16.69 | | 19 | 24.90 | | 20 | 43.51 | | 21 | 13.60 | | 22 | 73.92 | | 23 | 25.65 | | 24 | 42.52 | | 25 | 69.65 | | 26 | 30.25 | | 27 | 30.02 |
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| C5D5N | | 01-Ha | 1.97 | | 01-He | 3.43 (dd, 5, 12) | | 02-Ha | 4.50 | | 03-He | 4.19 (s, w1/2 = 10) | | 04-Ha | 1.77 | | 04-He | 2.00 | | 05-H | 3.02 (dd, 2, 9) | | 07-H | 6.25 (d, 2) | | 09-Ha | 3.82 (dd, 2, 9) | | 11-Ha | 4.45 | | 12-Ha | 2.95 (dd, 12, 12) | | 12-He | 2.48 (dd, 12, 17) | | 15-Ha | 1.86 | | 15-Hb | 2.02 | | 16-Ha | 1.59 | | 16-Hb | 2.23 | | 17-H | 2.64 | | 18-Me | 0.77 (s ) | | 19-Me | 1.31 (s ) | | 20-H | 2.11 (m, w1/2 = 24) | | 21-Me | 1.27 (d, 7) | | 22-H | 4.03 (m, w1/2 = 20) | | 23-Ha | 1.78 | | 23-Hb | 1.84 | | 24-Ha | 2.04 | | 24-Hb | 2.24 | | 26-Me | 1.37 (s ) | | 27-Me | 1.39 (s ) |
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| M.P. | | | [α]D20 | | | IR (Nujol) ν max (cm-1) | 3200 (OH), 1648 (cyclohexenone) | | UV (MeOH) λ max (log ε) | 299 (?) |
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| TLC | | | RLCC | solvent system H2O-EtOAc-n-PrOH (6:6:1) | | GLC | | | HPLC | Recycle HPLC : column Asahipack GS-320 (50 x 2 cm i.d.), solvent MeOH, flow-rate 3.5 ml.min-1. |
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Permanent link to this datasheet: 11α-HYDROXYECDYSONE
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