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Year of first isolation: |
2001 |
| Formula: | C30H46O6 |
| Molecular weight: | 502 |
| Occurence in plants: |
Rhaponticum uniflorum [Asteraceae] »  ![Wikipedia: Rhaponticum uniflorum [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C)CCC1C(OC(O1)(C)C)(C)C2CCC3(C2(CC=C4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1C2=CC[C@]2([C@]1(CC[C@@H]2[C@]1(C)[C@@H](CCC(C)C)OC(O1)(C)C)O)C)C » 
| | IUPAC Name | (2S,3R,5R,10S,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(4R,5R)-2,2,4-trimethyl-5-(3-methylbutyl)-1,3-dioxolan-4-yl]-2,3,4,5,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 10918141 | InChiKey
[ ChemIDPlus: search ] | SAOBRQOPFYGWSJ-ILGNCVIMSA-N | | InChI | InChI=1S/C30H46O6/c1-17(2)8-9-25-29(7,36-26(3,4)35-25)24-11-13-30(34)19-14-21(31)20-15-22(32)23(33)16-27(20,5)18(19)10-12-28(24,30)6/h10,14,17,20,22-25,32-34H,8-9,11-13,15-16H2,1-7H3/t20-,22+,23-,24-,25+,27+,28+,29+,30+/m0/s1 |
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| FAB-MS | 525 [M+Na]+, 509 [M+Li]+ | | EI-MS m/z (relative intensity %) | 487 [M-CH3]+, 469 [M-CH3-H2O]+, 444, 426, 402, 379, 361, 343, 325, 326, 317, 301, 299, 211, 185 | | CI-MS (NH3) m/z | |
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| CDCl3 | | 01 | 43.19 | | 02 | 68.05 | | 03 | 67.81 | | 04 | 37.22 | | 05 | 51.07 | | 06 | 203.18 | | 07 | 119.24 | | 08 | 154.24 | | 09 | 141.14 | | 10 | 37.13 | | 11 | 132.01 | | 12 | 38.31 | | 13 | 47.36 | | 14 | 84.93 | | 15 | 31.22 | | 16 | 22.35 | | 17 | 50.01 | | 18 | 17.74 | | 19 | 27.08 | | 20 | 83.16 | | 21 | 22.11 | | 22 | 82.23 | | 23 | 27.48 | | 24 | 37.62 | | 25 | 28.70 | | 26 | 22.76 | | 27 | 22.88 | | Me | 29.39, 29.68 | | O-C-O | 107.22 |
| CD3OD | | 01 | 38.0 | | 02 | 68.9 | | 03 | 68.9 | | 04 | 32.7 | | 05 | 51.4 | | 06 | 204.2 | | 07 | 118.3 | | 08 | 152.1 | | 09 | 142.7 | | 10 | 38.3 | | 11 | 131.9 | | 12 | 39.2 | | 13 | 48.1 | | 14 | 85.4 | | 15 | 31.7 | | 16 | 23.4 | | 17 | 50.3 | | 18 | 17.9 | | 19 | 25.1 | | 20 | 87.3 | | 21 | 22.7 | | 22 | 84.6 | | 23 | 26.7 | | 24 | 37.4 | | 25 | 28.9 | | 26 | 23.7 | | 27 | 24.7 | | Me | 27.9, 29.4 | | O-C-O | 108.5 |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | 3.69 (m) | | 03-He | 3.76 (m) | | 04-Ha | | | 04-He | | | 05-H | 2.40 (m) | | 07-H | 5.66 (br, s) | | 11-H | 6.22 (dd, 6.4, 2) | | 12-Ha | 2.73 (m, 2) | | 12-He | 2.43 (m, 6.5) | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.45 (m) | | 18-Me | 0.81 (s) | | 19-Me | 1.06 (s) | | 21-Me | 1.16 (s) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.88 (d, 6.7) | | 27-Me | 0.89 (d, 6.7) | | Me-ketal | 1.28 (s), 1.35 (s) |
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| M.P. | 235-237 °C ; | | [α]D20 | + 54.8 ? ° (c 0.8 ; MeOH) | | IR (KBr) ν max (cm-1) | 3400, 1665 | | UV (MeOH) λ max (log ε) | 287 (-) ; |
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| HPLC | | | GLC | | | HPTLC | | | TLC | N o t e: The same compound was later described under the name DACRYHAINANSTERONE 20,22-ACETONIDE by Olennikov in 2018 (see ref.) |
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Permanent link to this datasheet: 5-DEOXYKALADASTERONE 20,22-ACETONIDE
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