|
|
|
|
Year of first isolation: |
1999 |
| Formula: | C27H44O6 |
| Molecular weight: | 464 |
| Occurence in plants: |
Silene otites [Caryophyllaceae] »  ![Wikipedia: Silene otites [Caryophyllaceae]](/images/wikipedia.png)
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(CO)C(CCC(C)(C)O)O)O)C)O | 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([C@]1(CC[C@@H]2[C@H](CO)[C@@H](CCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (3S,5R,9R,10R,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-17-[(2R,3R)-1,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101142457 | InChiKey
[ ChemIDPlus: search ] | YUPATXHXAGHRCM-VQOIUDCISA-N | | InChI | InChI=1S/C27H44O6/c1-24(2,32)9-8-22(30)17(15-28)18-7-12-27(33)20-14-23(31)21-13-16(29)5-10-25(21,3)19(20)6-11-26(18,27)4/h14,16-19,21-22,28-30,32-33H,5-13,15H2,1-4H3/t16-,17-,18+,19-,21-,22+,25+,26+,27+/m0/s1 |
| |
| CI-MS (NH3) m/z | 482 (M+H+NH3)+, 465 (M.H), 452, 447 (base peak), 435, 429, 417, 411, 399, 393, 366, 349, 331, 313, 116 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
|
|
| D2O | | 01 | 29.2 | | 02 | | | 03 | 65.7 | | 04 | | | 05 | 52.3 | | 06 | | | 07 | 121.8 | | 08 | | | 09 | 37.4 | | 10 | 37.4 | | 11 | 21.0 | | 12 | 31.2 | | 13 | 48.0 | | 14 | 86.5 | | 15 | 31.4 | | 16 | 26.4 | | 17 | 44.4 | | 18 | 16.6 | | 19 | 24.2 | | 20 | 48.5 | | 21 | 62.2 | | 22 | 75.8 | | 23 | 27.1 | | 24 | 41.8 | | 25 | 72.7 | | 26 | 28.6 | | 27 | 29.2 |
|
| D2O | | 01-Ha | 1.36 | | 01-He | 1.85 | | 02-Ha | 1.36 | | 02-He | 1.68 | | 03-He | 4.10 (m, w1/2 = 25) | | 04-Ha | 1.62 | | 04-He | 1.76 | | 05-H | 2.40 (dd, 12.5, 2) | | 07-H | 5.97 (d, 2) | | 09-H | 3.14 (m, w1/2 = 26) | | 11-Ha | 1.66 | | 11-He | 1.81 | | 12-Ha | 1.91 | | 12-He | 1.75 | | 15-Ha | 2.09 | | 15-Hb | 1.64 | | 16-Ha | 1.97 | | 16-Hb | 1.62 | | 17-H | 2.07 | | 18-Me | 0.77 (s) | | 19-Me | 0.98 (s) | | 20-H | 1.92 | | 21-Ha | 3.90 (dd, 11.2, 4.1) | | 21-Hb | 3.76 (dd, 11.2, 7.2) | | 21-Me | ? | | 22-H | 3.78 | | 23-Ha | 1.53 | | 23-Hb | 1.67 | | 24-Ha | 1.48 | | 24-Hb | 1.82 | | 26-Me | 1.236 (s) | | 27-Me | 1.243 (s) |
|
| |
| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 242 (?) ; |
| |
| HPTLC | | | TLC | | | GLC | | | HPLC | NP system, Zorbax-SIL column (250 mm long, 4.6 mm. i.d.) solvent system cyclo-hexane-isopropanol-water (100:40:3 v/v/v), flow-rate 1 mL.min-1, Ret 14.8 min. |
| |
Drosophila melanogaster BII cell assay: EC50 = 4.3 x 10-6M |
| |
| |
Permanent link to this datasheet: 2-DEOXY-21-HYDROXYECDYSONE
|
|
