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Year of first isolation: |
1969 |
| Formula: | C27H44O2 |
| Molecular weight: | 400 |
| Occurence in plants: |
Peniocereus greggi [Cactaceae] »  ![Wikipedia: Peniocereus greggi [Cactaceae]](/images/wikipedia.png)
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| Occurence in animals: |
Locusta migratoria [Orthoptera] »
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| Canonical SMILES | CC(C)CCCC(C)C1CCC2C1(CCC3C2=CC(=O)C4C3(CCC(C4)O)C)C | 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(C1CC[C@@H]2[C@H](C)CCCC(C)C)C)C » 
C1[C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)C »
C1[C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)C »
| | IUPAC Name | 3S,5R,9R,10R,13R,14R,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one (14a-H) | | CAS-RN | 39219-58-4 | | PubChem CID | 56842747 | InChiKey
[ ChemIDPlus: search ] | AVFLDWQHIWZEHL-LJFHHSMUSA-N | | InChI | InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h16-19,21-24,28H,6-15H2,1-5H3/t18-,19+,21-,22+,23+,24+,26-,27-/m1/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | (for its 3-acetate): 442(M)+ | | HR-MS | |
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| CD2Cl2 | | 01 | 29.5 * | | 02 | 28.9 * | | 03 | 65.3 | | 04 | 36.2 | | 05 | 50.7 | | 06 | 202.0 | | 07 | 121.3 | | 08 | 165.0 | | 09 | 39.8 | | 10 | 38.2 | | 11 | 22.5 | | 12 | 39.7 | | 13 | 46.2 | | 14 | 56.7 | | 15 | 25.1 | | 16 | 28.1 | | 17 | 56.7 | | 18 | 12.3 | | 19 | 24.1 | | 20 | 34.1 | | 21 | 18.8 | | 22 | 36.6 | | 23 | 25.1 | | 24 | 39.7 | | 25 | 28.2 | | 26 | 22.5 $ | | 27 | 22.7 $ |
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| CDCl3 | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | 4.02 (m ) | | 04-Ha | | | 04-He | | | 05-H | 2.43 | | 07-H | 5.70 | | 09-Ha | 2.35 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | 2.15* | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.10* | | 18-Me | 0.59 | | 19-Me | 1.01 | | 21-Me | 0.93 | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.86 (d, 5) | | 27-Me | 0.86 (d, 5) |
| C6D6 (3-OAc) | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | 5.10 | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.72 | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.63 | | 19-Me | 0.98 | | 21-Me | | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | | | 27-Me | |
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| M.P. | 176-177 °C | | [α]D20 | + 60.2 ° (c 1.08; MeOH) | | IR (KBr) ν max (cm-1) | 1743, 1667, 1627, 1278 ; 1660, 1390, 1053 (free form) | | UV (CH3CN) λ max (log ε) | 243 (4.114) |
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| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC : column Spherisorb 5-ODS-2, solvent linear gradient (in 30 min) of 20% to 100% ACN-iPrOH (5:2) in 0.1% TFA in H2O, flow-rate 1 ml.min-1, Rt 39.9 min (2dE : 17.0 min, 2,22,25dE : 35.9 min) |
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| First isolation | KNIGHT, J.C. et al. (1969) Phytochemistry 8, 477-482 |
 | | General | GALBRAITH, M.N. et al. (1974) Aust. J. Chem. 27, 1087-1095 |
| | General | HORN, D.H.S. et al. (1976) Insect Biochem. 6, 601-604 |
| | First isolation | HETRU, C. et al. (1978) Life Sci. 22, 2141-2154 |
| | General | FAUX, A.F. et al. (1979) Insect Biochem. 9, 101-105 |
| | General | HAAG, T. et al. (1987) Insect Biochem. 17, 291-301 |
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Permanent link to this datasheet: 2,14,22,25-TETRADEOXYECDYSONE
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