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Year of first isolation: |
2023 |
| Formula: | C39H56O11 |
| Molecular weight: | 700 |
| Occurence in plants: |
Fibraurea incisa [Menispermaceae] »  ![Wikipedia: Fibraurea incisa [Menispermaceae]](/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=C3C2CC[C@@]4(C)[C@@]3(O)CC[C@@]4([C@](C)([C@H](O)C[C@@H](C)C(C)(O)C)O)[H])=O)([H])C[C@@H](O)[C@@H](OC(/C=C/C5=CC(OC)=C(O)C(OC)=C5)=O)C1 » 
| | IUPAC Name | (2S,3R,5R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-((2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | YZXUMPLPZGHEBG-NDVQSBSMSA-N | | InChI | InChI=1S/C39H56O11/c1-21(35(2,3)45)15-32(42)38(6,46)31-12-14-39(47)24-18-26(40)25-19-27(41)30(20-36(25,4)23(24)11-13-37(31,39)5)50-33(43)10-9-22-16-28(48-7)34(44)29(17-22)49-8/h9-10,16-18,21,23,25,27,30-32,41-42,44-47H,11-15,19-20H2,1-8H3/b10-9+/t21-,23?,25+,27-,30+,31+,32-,36-,37-,38-,39-/m1/s1 |
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| HRESIMQTOFMS (positive ion mode) m/z | 723.3721 [M+Na]+, calculated for C39H56O11 Na+ 723.3715 |
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| CD3OD | | 01 | 34.2 | | 02 | 72.5 | | 03 | 66.4 | | 04 | 32.9 | | 05 | 51.7 | | 06 | 205.8 | | 07 | 122.3 | | 08 | 168.1 | | 09 | 35.0 | | 10 | 39.6 | | 11 | 21.6 | | 12 | 32.5 | | 13 | 48.8 | | 14 | 85.2 | | 15 | 31.9 | | 16 | 21.4 | | 17 | 50.4 | | 18 | 18.1 | | 19 | 24.3 | | 20 | 78.0 | | 21 | 21.0 | | 22 | 75.4 | | 23 | 34.4 | | 24 | 41.7 | | 25 | 73.8 | | 26 | 27.5 | | 27 | 26.2 | | 28 | 14.9 | | O-Me [3]',[5]' | 56.0 | | [1]' | 126.7 | | [2]', [6]' | 106.9 | | [3]',[5]' | 139.7 | | [4]' | 139.7 | | [7]' | 147.2 | | [8]' | 116.1 | | [9]' | 168.5 |
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| CD3OD | | 01-Ha | 1.93 (m) | | 01-Hb | 1.63 (m) | | 02-Ha | 5.11 (ddd, 12.2, 4.1, 3.1) | | 03-Ha | 4.16 (br dd, 5.0, 3.1) | | 04-Ha | 1.88 (m) | | 04-Hb | 1.75 (m) | | 05-H | 2.48 (dd, 13.4, 4.1) | | 07-H | 5.85 (d, 2.4) | | 09-H | 3.29 (ddd, 11.2, 7.5, 2.4) | | 11-Ha | 1.74 (m) | | 11-Hb | 1.90 (m) | | 12-Ha | 1.90 (m) | | 12-Hb | 2.18 (td, 13.1, 4.9) | | 15-Ha | 1.98 (td, 11.5, 6.2) | | 15-Hb | 1.63 (m) | | 16-Ha | 1.75 (m) | | 16-Hb | 2.02 (m) | | 17-Ha | 2.37 (dd, 9.4, 8.8) | | 18-Me | 0.91 (s) | | 19-Me | 1.02 (s) | | 21-Me | 1.20 (s) | | 22-H | 3.47 (dd, 11.2, 1.0) | | 23-H | 1.75 (m), 1.20 (m) | | 24-H | 1.75 (m) | | 26-Me | 1.17 (m) | | 27-Me | 1.15 (m) | | 28-Me | 0.95 (d, 6.8) | | OMe-[3]', [5]' | 3.88 (s) | | [2]'-H, [6]'-H | 6.92 (s) | | [7]'-H | 7.68 (d, 15.9) | | [8]'-H | 6.42 (d, 15.9) |
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| M.P. | — °C ; | | [α]D20 | +2 ° (c 0.2 ; MeOH) | | IR (KBr) ν max (cm-1) | 3426, 2966, 1683, 1652, 1605, 1516; 1461, 1384, 1284, 1152, 1117, 978, 914, 876, 832 | | UV (MeOH) λ max (log ε) | nm (-) ; 204 (4.20), 226 (sh)(4.29), 241 (4.38),329 54.25) |
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Permanent link to this datasheet: 2-O-SINAPOYL MAKISTERONE A
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