|
|
|
|
Year of first isolation: |
1986 |
| Formula: | C27H42O6 |
| Molecular weight: | 462 |
| Occurence in plants: |
Laurencia pinnata [Rhodomelaceae] »  ![Wikipedia: Laurencia pinnata [Rhodomelaceae]](/images/wikipedia.png)
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4=CC(C(CC34C)O)O)C)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2(C(=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@@H](CCC(C)C)O)O)O)C)C » 
| | IUPAC Name | (2S,3S,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,9,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 162902990 | InChiKey
[ ChemIDPlus: search ] | QTZCCMVFFNRYMG-OUAVXPTCSA-N | | InChI | InChI=1S/C27H42O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h12-13,15-16,20-23,29-33H,6-11,14H2,1-5H3/t16-,20-,21-,22-,23+,24+,25+,26+,27+/m0/s1 |
| |
| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | FD-MS | 462 [M]+, 444, 351, 317, 145 |
|
|
| 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 | |
|
| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.21 (ddd, 10, 7, 3.5) | | 03-Ha | 4.64 (dd, 7, 2) | | 04-H | 6.79 (d, 2) | | 05-H | -- | | 07-H | 6.28 (d, 2) | | 09-Ha | 3.54 (ddd, 12, 7, 2) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | -- | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.94 (t, 9) | | 18-Me | 1.22 (s ) | | 19-Me | 1.26 (s ) | | 21-Me | 1.59 (s ) | | 22-Hb | 3.83 (d, 11) | | 23-Ha | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.84 (d, 6.7) | | 27-Me | 0.85 (d, 6.7) |
|
| |
| M.P. | 210-212 °C | | [α]D20 | +39° (c 0.35 ; MeOH) | | IR (KBr) ν max (cm-1) | 3450, 1685, 1655, 1075 | | UV (EtOH) λ max (log ε) | 256 (3.88) |
| |
| TLC | | | GLC | | | HPLC | preparative on Hitachi-gel #3011 (MeOH-H2O, 4:1) | | LC | preparative silica gel (Merck, 70-230 mesh), fraction eluting with EtOAc-MeOH (1:1) |
| |
| |
| |
Permanent link to this datasheet: 14-HYDROXYPINNASTEROL
|
|
