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Year of first isolation: |
1971 |
| Formula: | C36H50O9 |
| Molecular weight: | 626 |
| 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)C4(C3(CC(C(C4)O)OC(=O)C=CC5=CC=CC=C5)C)O)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](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@@H](CCC(C)(C)O)O)(C)O)O)C)O)C » 
| | IUPAC Name | [(2S,3R,5S,9R,10R,13R,14S,17S)-3,5,14-trihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-2-yl] (E)-3-phenylprop-2-enoate | | CAS-RN | | | PubChem CID | 149253462 | InChiKey
[ ChemIDPlus: search ] | IALQUIVFVGRAAS-WKNUBDMUSA-N | | InChI | InChI=1S/C36H50O9/c1-31(2,41)16-15-28(38)34(5,42)27-14-18-35(43)24-19-29(39)36(44)20-25(37)26(21-33(36,4)23(24)13-17-32(27,35)3)45-30(40)12-11-22-9-7-6-8-10-22/h6-12,19,23,25-28,37-38,41-44H,13-18,20-21H2,1-5H3/b12-11+/t23-,25+,26-,27-,28+,32+,33+,34+,35+,36+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 608 [M-18]+, 590, 572, 554, 510 [M-116(side chain)]+, 442 [M-148(cinnamic acid)-36]+, 361 [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 | |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 5.55 (m, w1/2=20) | | 03-He | 4.34 (m, w1/2=9) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.25 | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.19 (s ) | | 19-Me | 1.19 (s ) | | 21-Me | 1.55 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.38 (s ) | | 27-Me | 1.38 (s ) | | aromatic | 7.38 | | vinylic | 6.71, 7.97 (d, 16) |
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| M.P. | 268-270°C | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3400, 1700 (carbonyl), 1670, 1640 | | UV (EtOH) λ max (log ε) | 276 (4.332), 248 (sh), 223 (4.299), 200 (4.301) |
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| HPTLC | | | TLC | NP-TLC on silica gel : Rf 0.51 (CHCl3-EtOH, 90:10) (two developments) ; Rf 0.56 (CHCl3-EtOH, 80:20) | | GLC | decomposes on silylation | | 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: POLYPODINE B 2-CINNAMATE
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