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Year of first isolation: |
2005 |
| Formula: | C32H48O8 |
| Molecular weight: | 560 |
| Occurence in plants: |
Cyathula officinalis [Asteraceae] »  ![Wikipedia: Cyathula officinalis [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@@H]3[C@H]1OC(O3)(C)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@@H]1[C@H](OC(=O)[C@@H]1C)C)O)O)O)C)C » 
| | IUPAC Name | (1S,3aS,5aR,6aR,9aS,10aR,10bR,12aR)-1-((2R,3R)-4-((2R,3S,4R)-2,4-dimethyl-5-oxotetrahydrofuran-3-yl)-2,3-dihydroxybutan-2-yl)-3a-hydroxy-8,8,10a,12a-tetramethyl-1,2,3,3a,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-5H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-5-one | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | CMPNZMGFQLFLPL-GRFLDNIISA-N | | InChI | InChI=1S/C32H48O8/c1-16-18(17(2)38-27(16)35)12-26(34)31(7,36)25-9-11-32(37)20-13-22(33)21-14-23-24(40-28(3,4)39-23)15-29(21,5)19(20)8-10-30(25,32)6/h13,16-19,21,23-26,34,36-37H,8-12,14-15H2,1-7H3/t16-,17-,18+,19+,21+,23-,24+,25+,26-,29-,30-,31-,32-/m1/s1 |
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| EI-MS m/z (relative intensity %) | | | ESI-MS m/z | 559 [M-H]? (negative mode); 583 [M+Na]+, 1143 [2M+Na]+ (positive mode) | | HR-ESIMS (negative mode) | 559.3271 [M-1]? calc. for C32H47O8 559.3270 |
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| C5D5N | | 01 | 38.0 (t) | | 02 | 72.2 (d) | | 03 | 71.9 (d) | | 04 | 26.7 (t) | | 05 | 51.3 (d) | | 06 | 202.0 (s) | | 07 | 121.8 (d) | | 08 | 165.1 (s) | | 09 | 34.8 (d) | | 10 | 37.8 (s) | | 11 | 20.9 (t) | | 12 | 31.4 (t) | | 13 | 48.1 (s) | | 14 | 83.8 (s) | | 15 | 31.7 (t) | | 16 | 21.4 (t) | | 17 | 49.7 (d) | | 18 | 17.5 (q) | | 19 | 23.6 (q) | | 20 | 76.5 (s) | | 21 | 21.1 (q) | | 22 | 74.8 (d) | | 23 | 26.4 (d) | | 24 | 39.6 (d) | | 25 | 26.4 (d) | | 26 | 179.8 (s) | | 27 | 12.6 (q) | | 28 | 78.4 (d) | | 29 | 17.3 (q) | | Me | 28.6 (q), 26.4 (q) | | OCO | 107.9 (s) |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 4.18 (m) | | 03-He | 4.08 (br, s) | | 04-Ha | | | 04-He | | | 05-H | 2.56 (d, 12.0) | | 07-H | 6.19 (s) | | 09-H | 3.58 (br, s) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.48 (q, 11.2) | | 16-Hb | | | 17-H | 3.13 (t, 9.0) | | 18-Me | 1.18 (s) | | 19-Me | 0.99 (s) | | 21-Me | 1.59 (s) | | 22-H | 3.80 (d, 10.8) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | 3.19 (qui, 7.8) | | 27-Me | 1.25 (d, 7.8) | | 28-H | 4.63 (qui, 6.6) | | 29-Me | 1.26 (d, 6.6) | | Me2C= | 1.54 (3H, s), 1.30 (3H, s) |
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| M.P. | 260-262 °C ; | | [α]D25 | + 42.2 ° (c 0.12 ; MeOH) | | IR (KBr) ν max (cm-1) | 3458, 1754, 1656 | | UV (MeOH) λ max (log ε) | 242 (3.98) ; |
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| HPLC | NP-HPLC column Merck KGaA-Diol (250 mm long, 4 mm i.d.), eluted with CH2Cl2-MeOH 98:2, flow-rate 1 ml.min?1, ret 21.99 min. | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: ISOCYASTERONE 2,3-MONOACETONIDE
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