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Year of first isolation: |
2014 |
| Formula: | C29H44O8 |
| Molecular weight: | 520 |
| Occurence in plants: |
Diplopterygium rufopilosum [Gleicheniaceae] »  ![Wikipedia: Diplopterygium rufopilosum [Gleicheniaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CCC1(CC(OC(=O)C1C)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@@]([C@@H]1OC(=O)[C@@H]([C@@](C1)(O)CC)C)(C)O)O)C)C » 
| | IUPAC Name | (3R,4R,6R)-4-ethyl-4-hydroxy-6-[(1R)-1-hydroxy-1-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-methyloxan-2-one | | CAS-RN | | | PubChem CID | 102236818 | InChiKey
[ ChemIDPlus: search ] | FCULMERLXQWQQI-JHPMPEKDSA-N | | InChI | InChI=1S/C29H44O8/c1-6-28(35)14-23(37-24(33)15(28)2)27(5,34)22-8-10-29(36)17-11-19(30)18-12-20(31)21(32)13-25(18,3)16(17)7-9-26(22,29)4/h11,15-16,18,20-23,31-32,34-36H,6-10,12-14H2,1-5H3/t15-,16-,18+,20+,21-,22-,23+,25+,26+,27+,28+,29+/m0/s1 |
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| HRESI-MS | (negative) [M-H] 519.2953 (calculated 519.2958 for C29H43O8) | | EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | |
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| CDCl3 | | 01 | 36.9 (t) | | 02 | 67.4 (d) | | 03 | 67.2 (d) | | 04 | 31.3 (t) | | 05 | 50.2 (d) | | 06 | 203.7 (s) | | 07 | 121.5 (d) | | 08 | 164.7 (s) | | 09 | 33.7 (d) | | 10 | 38.1 (s) | | 11 | 20.4 (t) | | 12 | 31.3 (t) | | 13 | 47.4 (s) | | 14 | 84.1 (s) | | 15 | 33.0 (t) | | 16 | 20.4 (t) | | 17 | 49.0 (d) | | 18 | 17.5 (q) | | 19 | 23.9 (d) | | 20 | 75.8 (s) | | 21 | 20.8 (q) | | 22 | 78.1 (d) | | 23 | 31.2 (t) | | 24 | 83.2 (s) | | 25 | 51.7 (d) | | 26 | 177.5 (s) | | 27 | 8.9 (q) | | 28 | 33.1 (t) | | 29 | 7.2 (q) |
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| CDCl3 | | 01-Ha | 1.34 (dd, 12.6, 2.1) | | 01-He | 1.74 (dd, 12.6, 2.1) | | 02-Ha | 3.89 (m) | | 03-He | 3.82 (m) | | 04-Ha | 1.65 (m) | | 04-He | 1.61 (m) | | 05-H | 2.36 (dd, 9.5, 2.1) | | 07-H | 5.68 (s) | | 09-H | 3.15 (dd, 9.5, 2.1) | | 11-Ha | 1.70 (m) | | 11-He | 1.68 (m) | | 12-Ha | 2.17 (m) | | 12-He | 1.88 (m) | | 15-Ha | 1.95 (m) | | 15-Hb | 1.60 (m) | | 16-Ha | 1.70 (m) | | 16-Hb | 1.68 (m) | | 17-H | 2.32 (dd, 9.0, 2.0) | | 18-Me | 0.88 (s) | | 19-Me | 0.90 (s) | | 21-Me | 1.23 (s) | | 22-H | 4.02 (dd, 10.8, 2.8) | | 23-Ha | 1.36 (dd, 10.8, 2.8) | | 23-Hb | 1.92 (dd, 10.8, 10.6) | | 25-H | 2.30 (q, 7.5) | | 27-Me | 0.86 (d, 7.5) | | 28-Ha | 1.25 (m) | | 28-Hb | 1.75 (m) | | 29-H | 0.82 (m) |
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| M.P. | °C ; | | [α]D23.3 | -5.37 ° (c 0.021; MeOH) | | IR (KBr) ν max (cm-1) | 3345 (OH), 2965, 1775 (carbonyl), 1710, 1640 (olefinic), 1456, 1056, 875 | | UV (CDCl3) λ max (log ε) | 242 (4.01) ; |
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| RP-HPLC | column 220 mm x 25 mm, 10 m, Merck C18, 15 mL/min, MeOH/H2O gradient 45 to 70%, retention time 18.5 min. | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 2,3,14,20,24-PENTAHYDROXY-6,26-DIOXO-STIGMAST-7-ENE-22,26-OLIDE
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