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Year of first isolation: |
2020 |
| Formula: | C29H44O11 |
| Molecular weight: | 568 |
| Occurence in plants: |
Rhaponticum acaule [Asteraceae] »  ![Wikipedia: Rhaponticum acaule [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@@]12[C@@](C(C=C3C2[C@H](O)C[C@@]4(C)[C@@]3(O)CC[C@@H]4[C@](C)([C@H](O)CC5(O)C(C)(C)OC(C5O)=O)O)=O)([H])C[C@@H](O)[C@@H](O)C1 » 
| | IUPAC Name | 4-((2R,3R)-2,3-dihydroxy-3-((2S,3R,5R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)butyl)-3,4-dihydroxy-5,5-dimethyldihydrofuran-2(3H)-one | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | FHHPAOMWMLUKQV-IXOTWIQESA-N | | InChI | InChI=1S/C29H44O11/c1-24(2)29(39,22(35)23(36)40-24)12-20(34)27(5,37)19-6-7-28(38)14-9-15(30)13-8-16(31)17(32)10-25(13,3)21(14)18(33)11-26(19,28)4/h9,13,16-22,31-35,37-39H,6-8,10-12H2,1-5H3/t13-,16+,17-,18+,19-,20+,21?,22?,25-,26+,27+,28+,29?/m0/s1 |
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| HRESIMS (negative ion mode) m/z | 567.2810 [M-H]–, (positive mode 569.2950 [M+H]+, calc. for C29H44O11 568.2884 |
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| CD3OD | | 01 | 39.0 | | 02 | 68.9 | | 03 | 68.5 | | 04 | 33.2 | | 05 | 52.7 | | 06 | 206.7 | | 07 | 122.9 | | 08 | 168.4 | | 09 | 42.9 | | 10 | 39.9 | | 11 | 69.4 | | 12 | 43.6 | | 13 | 48.5 | | 14 | 85.0 | | 15 | 31.9 | | 16 | 21.5 | | 17 | 50.2 | | 18 | 18.8 | | 19 | 24.6 | | 20 | 77.6 | | 21 | 20.8 | | 22 | 77.1 | | 23 | 35.2 | | 24 | 89.3 | | 25 | 80.0 | | 26 | 24.7 | | 27 | 11.3 | | 28 | 74.4 | | 29 | 176.9 |
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| CD3OD | | 01-Ha | 1.38 (dd "t" 12.8) | | 01-Hb | 2.58 (ss, 12.8, 4.3)) | | 02-Ha | 4.01 (ddd, 11.7, 7.2, 2.8) | | 03-He | 3.98 (ddd "br d", 2.7) | | 04-Ha | 1.70 (brd) | | 04-Hb | 1.70 | | 05-H | 2.36 (dd, 13.0, 3.6) | | 07-H | 5.84 (d, 2.4) | | 09-H | 3.16 (dd, 8.9, 2.6) | | 11-H | 4.12 (ddd, 12.0, 8.9, 6.3) | | 12-Ha | Z.Z1 (dd "t", 12.0, 12.0) | | 12-Hb | 2.01 (dd;, 12/0, 6.3) | | 15-Ha | 1.82 | | 15-Hb | 1.80 (m) | | 16-Ha | 1.6Z (m) | | 16-Hb | 2.01 (m) | | 17-H | 2.35 (ss "t", 8.3) | | 18-Me | 0.89 (s) | | 19-Me | 1.06 (s) | | 21-Me | 1.27 (s) | | 22-H | 3.29 (br d, 11.1) | | 23-Ha | 1.89 (ddd "brd", 15.9) | | 23-Hb | 1.71 | | 26-Me | 1.41 (s) | | 27-Me | 1.46 (s) | | 28-H | 4.57 (s) |
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| M.P. | — °C ; | | [α]D25 | + 35.0° (c 0.08 ; MeOH) | | IR (KBr) ν max (cm-1) | 3326, 2943, 2835, 1736, 1656, 1443, 1217, 1110, 1021 | | UV (MeOH) λ max (log ε) | 232 nm (-) ; |
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Permanent link to this datasheet: ACAULESTERONE
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