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Year of first isolation: |
1971 |
| Formula: | C36H50O8 |
| Molecular weight: | 610 |
| Occurence in plants: |
Dacrydium intermedium [Podocarpaceae] »  ![Wikipedia: Dacrydium intermedium [Podocarpaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)OC(=O)C=CC5=CC=CC=C5)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)/C=C/c1ccccc1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | [(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] (E)-3-phenylprop-2-enoate | | CAS-RN | | | PubChem CID | 101704303 | InChiKey
[ ChemIDPlus: search ] | DXVLKBLMTNJMNC-JPKZWUAGSA-N | | InChI | InChI=1S/C36H50O8/c1-32(2,41)16-15-30(39)35(5,42)29-14-18-36(43)24-19-26(37)25-20-27(38)28(21-33(25,3)23(24)13-17-34(29,36)4)44-31(40)12-11-22-9-7-6-8-10-22/h6-12,19,23,25,27-30,38-39,41-43H,13-18,20-21H2,1-5H3/b12-11+/t23-,25-,27+,28-,29-,30+,33+,34+,35+,36+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 610 [M]+, 592, 574, 556, 494 [M-116 (side chain)]+, 426 [M-148 (cinnamic acid) - 36]+, 345 [M-148 -117]+, 148 (cinnamic acid), 147 (100%) (cinnamoyloxy), 131 (cinnamoyl). | | HR-MS | |
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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 | | | 28 | | | 29 | |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 5.42 (m, w1/2=20) | | 03-He | 4.37 (m, w1/2=9) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.25 | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.21 (s ) | | 19-Me | 1.11 (s ) | | 21-Me | 1.57 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.38 (s ) | | 27-Me | 1.38 (s ) | | Other | vinylic 6.60, 7.92 (d, 16); aromatic 7.38 |
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| M.P. | 258-260 °C ; | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3400 (OH), 1700 (carbonyl), 1646 (cyclohexenone). | | UV (EtOH) λ max (log ε) | 276 (4.332), 248 (sh), 223 (4.301), 200 (4.301); |
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| HPTLC | | | TLC on silica | Rf 0.44 (CHCl3-EtOH 9:1 v/v, two elutions); Rf 0.53 (CHCl3-EtOH 4:1) RP-TLC on paraffin coated silica gel Rf 0.00 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.00 (MeOH-H2O 65:35) | | TLC | | | GLC | | | HPLC | |
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Musca assay: 10% (20-hydroxyecdysone = 100%) |
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| First isolation | RUSSEL, G.B. et al. (1971) J. Chem. Soc., Chem. Commun., 71 |
 | | General | RUSSEL, G.B. et al. (1972) Aust. J. Chem. 25, 1935-1941 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | WILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 2-CINNAMATE
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