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Year of first isolation: |
1986 |
| Formula: | C45H74O7 |
| Molecular weight: | 726 |
| Occurence in plants: |
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| Occurence in animals: |
Boophilus microplus [Ixodidae] »  ![Wikipedia: Boophilus microplus [Ixodidae]](/images/wikipedia.png)
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| Canonical SMILES | CCCCCC=CCC=CCCCCCCCC(=O)OC(CCC(C)(C)O)C(C)C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)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]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)OC(=O)CCCCCCC/C=CC/C=CCCCCC)O)C)C » 
| | IUPAC Name | [(2S)-6-hydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-yl] (9Z,12Z)-octadeca-9,12-dienoate | | CAS-RN | | | PubChem CID | 66869683 | InChiKey
[ ChemIDPlus: search ] | IROYYLZGUUWNHR-GMFNZGFESA-N | | InChI | InChI=1S/C45H74O7/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-41(49)52-40(25-26-42(3,4)50)32(2)33-24-28-45(51)35-29-37(46)36-30-38(47)39(48)31-43(36,5)34(35)23-27-44(33,45)6/h11-12,14-15,29,32-34,36,38-40,47-48,50-51H,7-10,13,16-28,30-31H2,1-6H3/b12-11-,15-14-/t32-,33+,34-,36-,38+,39-,40?,43+,44+,45+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | FAB-MS (matrix tetraethyleneglycol TEG) m/z (relative intensity %) | 921 (M + H +TEG)+ (2), 727 (M+H)+ (8), 709 (31), 691 (2), 447 (9), 429 (100), 411 (80), 393. | | 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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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | | | 19-Me | | | 20-H | | | 21-Me | | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | | | 27-Me | |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | Rf 0.15 (silica gel, CHCl3-EtOH 9:1); Rf 0.40 (C8-bonded silica gel, MeOH-H2O 19:1), other solvent systems also described with C18,C2, and CN bonded silica gel. | | GLC | (of fatty acid methyl ester) | | HPLC | 1- Retention time 24.5 min [Partisil 5 (Whatman), 250 mm x 4.6 mm i.d., solvent dichloroethane-iPrOH-H2O 125:24:1 v/v/v, flow-rate 1 ml.min-1]: 2- Retention time 17 min [Ultrasphere-ODS (Beckman) 250 mm x 4.6 mm i.d., solvent linear gradient (30 min) of MeOH in H2O from 9:1 to 1:0 v/v, flow-rate 1 ml.min-1] |
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| General | WIGGLESWORTH, K.P. et al. (1985) Arch. Insect Biochem. Physiol. 2, 39-54 |
 | | General | HOFFMANN, K.H. et al. (1985) Life Sci. 37, 185-192 |
| | First isolation | CROSBY, T. et al. (1986) Biochem. J. 240, 131-138 |
| | General | ROBINSON, P.D. et al. (1987) Physiol. Entomol. 12, 321-330 |
| | General | DINAN, L. et al. (1987) J. Chromatogr. 411, 379-392 |
| | General | DINAN, L. et al. (1988) J. Steroid Biochem. 31, 237-245 |
| | General | DINAN, L. et al. (1988) J. Chromatogr. 436, 279-288 |
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Permanent link to this datasheet: ECDYSONE 22-LINOLEATE
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