|
|
|
|
Year of first isolation: |
1995 |
| Formula: | C28H38O3 |
| Molecular weight: | 422 |
| Occurence in plants: |
Calvatia cyathiformis [Fungi] »  ![Wikipedia: Calvatia cyathiformis [Fungi]](/images/wikipedia.png)
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CC(C)C(C)C=CC(C)C1CCC2(C1(CC=C3C2=CC(=O)C4=CC(=O)CCC34C)C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2(C(=CC(=O)C1)C(=O)C=C1C2=CC[C@]2([C@]1(CC[C@@H]2[C@H](C)/C=C/[C@@H](C(C)C)C)O)C)C » 
| | IUPAC Name | (10R,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-14-hydroxy-10,13-dimethyl-1,2,12,15,16,17-hexahydrocyclopenta[a]phenanthrene-3,6-dione | | CAS-RN | 162857-85-4 | | PubChem CID | 10251684 | InChiKey
[ ChemIDPlus: search ] | JABICPUHELULCU-OCOXMEBRSA-N | | InChI | InChI=1S/C28H38O3/c1-17(2)18(3)7-8-19(4)21-11-14-28(31)23-16-25(30)24-15-20(29)9-12-26(24,5)22(23)10-13-27(21,28)6/h7-8,10,15-19,21,31H,9,11-14H2,1-6H3/b8-7+/t18-,19+,21+,26+,27+,28+/m0/s1 |
| |
| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 422.2815 [M]+ (2), C28H38O3 requires 424.2820, 404 [M - H2O]+ (60), 280 (55), 265 (38). | | HR-MS | |
|
|
| CDCl3 | | 01 | 34.5 | | 02 | 34.3 | | 03 | 199.7 | | 04 | 127.0 | | 05 | 156.3 | | 06 | 188.7 | | 07 | 121.8 | | 08 | 156.0 | | 09 | 138.5 | | 10 | 38.8 | | 11 | 132.9 | | 12 | 37.4 | | 13 | 46.3 | | 14 | 84.7 | | 15 | 31.2 | | 16 | 27.2 | | 17 | 50.4 | | 18 | 16.2 | | 19 | 29.5 | | 20 | 40.1 | | 21 | 20.9 | | 22 | 135.4 | | 23 | 133.3 | | 24 | 42.9 | | 25 | 33.2 | | 26 | 20.0 | | 27 | 19.7 | | 28 | 17.6 |
|
| CDCl3 | | 01-Ha | 2.28 (ddd, 5.5, 13.6, 14.3) | | 01-Hb | 2.42 (ddd, 4.5, 5.1, 13.6) | | 02-Ha | 2.65 (ddd, 5.1, 14.3, 19.4) | | 02-Hb | 2.59 (ddd, 4.5, 5.5, 19.4) | | 04-H | 6.45 (s) | | 07-H | 6.17 (s) | | 11-H | 6.22 (dd, 1.8, 6.6) | | 12-Ha | 2.72 (dd, 1.8, 18.3) | | 12-He | 2.38 (dd, 6.6, 18.3) | | 15-Ha | 2.00 (m) | | 15-Hb | 1.77 (m) | | 16-Ha | 2.00 (m) | | 16-Hb | 1.44 (m) | | 17-H | 2.11 (m) | | 18-Me | 0.76 (s) | | 19-Me | 1.46 (s) | | 20-H | 2.09 (m) | | 21-Me | 1.04 (d, 5.9) | | 22-H | 5.22 (dd, 7.7, 15.4) | | 23-H | 5.30 (dd, 7.7, 15.4) | | 24-H | 1.89 (m) | | 25-H | 1.50 (m) | | 26-Me | 0.84 (d, 6.9) | | 27-Me | 0.85 (d, 6.9) | | 28-Me | 0.93 (d, 6.6) |
|
| |
| M.P. | 190-192 °C ; | | [α]D20 | + 93 ? ° (c 0.39; CHCl3) | | IR (KBr) ν max (cm-1) | 3450 (OH), 1660 (CO) | | UV (MeOH) λ max (log ε) | 250 (4.35) ;340 (4.06) |
| |
| |
| |
| |
Permanent link to this datasheet: CALVASTEROL A
|
|
