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Year of first isolation: |
2004 |
| Formula: | C27H42O8 |
| Molecular weight: | 494 |
| Occurence in plants: |
Serratula wolffii [Asteraceae] »  ![Wikipedia: Serratula wolffii [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CC=C3C(=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1C2=CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)O)C » 
| | IUPAC Name | (2S,3R,5S,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,12,15,16,17-octahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 102157616 | InChiKey
[ ChemIDPlus: search ] | IPPARPMLJLUMNP-CVFUVVIBSA-N | | InChI | InChI=1S/C27H42O8/c1-22(2,32)9-8-20(30)25(5,33)19-7-11-26(34)16-12-21(31)27(35)14-18(29)17(28)13-24(27,4)15(16)6-10-23(19,26)3/h6,12,17-20,28-30,32-35H,7-11,13-14H2,1-5H3/t17-,18+,19-,20+,23+,24+,25+,26+,27+/m0/s1 |
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| FAB-MS m/z (relative intensity %) | 495 [M+H]+ (9), 477 [M+H-H2O]+ (10), 459 [M+H-2H2O]+ (23), 443 (26), 440 (11), 422 (8), 407 (49), 394 (17), 378 (9), 361 (26), 359 (10), 323 (18), 300 (100), 199 (11) | | EI-MS m/z (relative intensity %) | | | HRE-SIMS m/z | 494.2885 (calculated 494.2880 for C27H42O8) |
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| CD3OD | | 01 | 34.5 | | 02 | 68.6 | | 03 | 70.3 | | 04 | 39.2 | | 05 | 80.5 | | 06 | 203.1 | | 07 | 117.9 | | 08 | 156.5 | | 09 | 137.9 | | 10 | 46.4 | | 11 | 134.3 | | 12 | 39.2 | | 13 | 48.0 | | 14 | 84.5 | | 15 | 31.5 | | 16 | 21.8 | | 17 | 50.7 | | 18 | 18.2 | | 19 | 26.5 | | 20 | 77.8 | | 21 | 20.9 | | 22 | 78.6 | | 23 | 27.5 | | 24 | 42.5 | | 25 | 71.4 | | 26 | 29.1 | | 27 | 29.9 |
| DMSO-d6 | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | 78.4 | | 06 | | | 07 | 116.5 | | 08 | | | 09 | 136.3 | | 10 | | | 11 | 131.7 | | 12 | 37.5 | | 13 | 46.3 | | 14 | 82.0 | | 15 | | | 16 | 20.4 | | 17 | 48.7 | | 18 | 17.3 | | 19 | 25.8 | | 20 | 75.5 | | 21 | 20.7 | | 22 | 76.3 | | 23 | 26.1 | | 24 | 41.4 | | 25 | 68.7 | | 26 | 29.0 | | 27 | 30.0 |
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| CD3OD | | 01-Ha | 2.05 | | 01-He | 2.05 | | 02-Ha | 3.83 (ddd, 10.7, 5.4, 3.2) | | 03-He | 3.88 (q, 3.0) | | 04-Ha | 1.77 (dd, ?, 3.4) | | 04-He | 1.92 (dd, 14.5, 2.8) | | 05-H | - | | 07-H | 5.83 (t, 1.2) | | 09-H | - | | 11-H | 6.34 (dt, 6.7, 2.0) | | 12-Ha | 2.726 (dd, 18.0, 1.8) | | 12-He | 2.436 (dd, 18.2, 6.7) | | 15-Ha | 1.80 | | 15-Hb | 1.98 | | 16-Ha | 1.79 | | 16-Hb | 1.99 | | 17-H | 2.49 (t, 9.0) | | 18-Me | 0.90 (s) | | 19-Me | 1.05 (s) | | 21-Me | 1.208 (s) | | 22-H | 3.35 (dd, 10.3, 1.8) | | 23-Ha | 1.30 | | 23-Hb | 1.68 | | 24-Ha | 1.44 (ddd, 13.3, 11.6, 4.2) | | 24-Hb | 1.81 | | 26-Me | 1.19 (s) | | 27-Me | 1.206 (s) |
| DMSO-d6 | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.65 (s) | | 09-H | | | 11-H | 6.18 (s, br) | | 12-Ha | 2.59 (d, 17.8) | | 12-He | 2.29 (dd, 17.8, 6.6) | | 15-Ha | | | 15-Hb | | | 16-Ha | 1.60* | | 16-Hb | 1.89* | | 17-H | 2.36 (t, 9.3) | | 18-Me | 0.77 (s) | | 19-Me | 0.96 (s, b) | | 21-Me | 1.075 (s) | | 22-H | 3.13 (d, 10.2) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.06 (s) | | 27-Me | 1.09 (s) |
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| M.P. | 218 °C (dec.) ; | | [α]D28 | + 59 ° (c 0.1 ; DMSO) | | IR (KBr) ν max (cm-1) | 3560-3200, 1650, 1602 | | UV (MeOH) λ max (log ε) | 296 (4.02) ; |
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| LC | Low pressure RP, MeOH-H2O (45:55) | | HPLC | NP on silica (Zorbax-SIL), solvent CH2Cl2-iPrOH-H2O (125:40:3) | | GLC | | | TLC | |
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Permanent link to this datasheet: HERKESTERONE
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