|
|
|
|
Year of first isolation: |
1992 |
| Formula: | C27H42O7 |
| Molecular weight: | 478 |
| Occurence in plants: |
Serratula tinctoria [Asteraceae] »  ![Wikipedia: Serratula tinctoria [Asteraceae]](/images/wikipedia.png)
Cyanotis arachnoidea [Commelinaceae] »
Leuzea carthamoides [Asteraceae] »
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(=O)CCC(C)(C)O)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]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(C(=O)CCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 14442966 | InChiKey
[ ChemIDPlus: search ] | IILSBUXFTVZCJS-DPROJNMLSA-N | | InChI | InChI=1S/C27H42O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-21,29-30,32-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,24+,25+,26+,27+/m0/s1 |
| |
| CI-MS (NH3) m/z | 496 (M+H+NH3)+, 479 (M+H)+, 461, 443, 425, 363, 345, 329, 327, 320 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
|
|
| C5D5N | | 01 | 38.0 | | 02 | 68.1 | | 03 | 68.1 | | 04 | 32.7 | | 05 | 51.4 | | 06 | 203.4 | | 07 | 121.8 | | 08 | 165.6 | | 09 | 32.4 | | 10 | 38.7 | | 11 | 21.7 | | 12 | 31.8 | | 13 | 48.2 | | 14 | 84.1 | | 15 | 31.9 | | 16 | 21.7 | | 17 | 51.6 | | 18 | 17.7 | | 19 | 24.4 | | 20 | 81.4 | | 21 | 25.7 | | 22 | 217.0 | | 23 | 45.9 | | 24 | 38.4 | | 25 | 69.0 | | 26 | 30.0 | | 27 | 29.9 |
| CD3OD | | 01 | 37.37 | | 02 | 68.70 | | 03 | 68.51 | | 04 | 32.74 | | 05 | 51.80 | | 06 | 206.36 | | 07 | 122.19 | | 08 | 167.58 | | 09 | 35.11 | | 10 | 39.28 | | 11 | 21.51 | | 12 | 32.48 | | 13 | =49.0 | | 14 | 85.14 | | 15 | 31.81 | | 16 | 21.69 | | 17 | 51.64 | | 18 | 17.91 | | 19 | 24.39 | | 20 | 82.02 | | 21 | 25.37 | | 22 | 217.29 | | 23 | 32.86 | | 24 | 38.14 | | 25 | 70.68 | | 26 | 29.21 | | 27 | 29.21 |
|
| D2O | | 01-Ha | 1.40 (dd, 13,12) | | 01-Hb | 1.89 | | 02-Ha | 3.88 (m, w1/2=22) | | 03-He | 3.04 (m, w1/2=8) | | 04-Ha | 1.78 | | 04-He | 1.78 | | 05-H | 2.42 (dd, 14,4.5) | | 07-H | 5.84 (d, 2.5) | | 09-Ha | 2.98 (m, w1/2=22) | | 11-Ha | 1.78 | | 11-He | 1.93 | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | 1.64 | | 16-Hb | 1.78 | | 17-H | 2.59 (m ) | | 18-Me | 0.87 (s ) | | 19-Me | 1.02 (s ) | | 21-Me | 1.51 (s ) | | 23-Ha | 2.80 (m, w1/2=19) | | 23-Hb | 2.80 (m ) | | 24-Ha | 1.76 | | 24-Hb | 1.76 | | 26-Me | 1.25 (s ) | | 27-Me | 1.25 (s ) |
|
| |
| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
| |
| HPTLC | | | TLC | | | GLC | | | HPLC | NP-HPLC, Ret 10.2 min (Column Zorbax-Sil, 25 cm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O, 125:25:2 v/v/v, flow-rate 1ml.min-1) (20E 25.2 min); Ret 16.7 min (Column Zorbax-Sil, 25 cm x 4.6 mm i.d., solvent isoC8-iPrOH-H2O, 100:30:2 v/v/v, flow-rate 1ml. min-1) (20E 22.6 min). RP-HPLC, Ret 14.0 min (Column Spherisorb-5ODS2, 25 cm x 4.6 mm i.d., solvent linear gradient 20 to 70% ACN in 1? TFA in H2O, flow-rate 1ml.min-1) (20E 12.3 min) |
| |
| |
| General | HEDTMAN, U. et al. (1989) Angew. Chem., Int. Ed. Engl. 28, 1515-1518 |
 | | General | HEDTMAN, U. et al. (1991) Tetrahedron 47, 3753-3772 |
| | First isolation | RUDEL, D. et al. (1992) Planta Med. 58, 358-364 |
| | Identification | VOKÁČ, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 |
| | Identification | KIUCHI, M. et al. (2003) Arch. Insect Biochem. Physiol. 52, 35-44 |
| | Identification | TAN, C. et al. (2003) Acta Pharm. Sinica 83, 760-762 |
|
| |
Permanent link to this datasheet: 22-OXO-20-HYDROXYECDYSONE
|
|
