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Year of first isolation: |
1988 |
| Formula: | C33H54O12 |
| Molecular weight: | 642 |
| Occurence in plants: |
Pfaffia iresinoides [Amaranthaceae] »  ![Wikipedia: Pfaffia iresinoides [Amaranthaceae]](/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]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)C[C@@H](C(C)C)O[C@@H]1OC([C@H](C(C1O)O)O)CO)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,10R,13R,14S,17S)-17-((2R,3R,5S)-2,3-dihydroxy-6-methyl-5-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)heptan-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | WVEMRTZARQEUPR-WHEWAJECSA-N | | InChI | InChI=1S/C33H54O12/c1-15(2)22(44-29-28(41)27(40)26(39)23(14-34)45-29)12-25(38)32(5,42)24-7-9-33(43)17-10-19(35)18-11-20(36)21(37)13-30(18,3)16(17)6-8-31(24,33)4/h10,15-16,18,20-29,34,36-43H,6-9,11-14H2,1-5H3/t16-,18-,20+,21-,22-,23?,24-,25+,26+,27?,28?,29+,30+,31+,32+,33+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| C5D5N | | 01 | 38.0 | | 02 | 68.3 | | 03 | 68.2 | | 04 | 32.6 | | 05 | 51.5 | | 06 | 203.6 | | 07 | 121.7 | | 08 | 166.3 | | 09 | 34.5 | | 10 | 38.8 | | 11 | 21.2 | | 12 | 32.1 | | 13 | 48.1 | | 14 | 84.2 | | 15 | 31.8 | | 16 | 21.6 | | 17 | 49.9 | | 18 | 18.0 | | 19 | 24.6 | | 20 | 76.8 | | 21 | 21.6 | | 22 | 75.4 | | 23 | 36.1 | | 24 | 84.7 | | 25 | 32.1 | | 26 | 17.3 | | 27 | 19.5 | | glu-1' | 105.9 | | glu-2' | 75.5 | | glu-3' | 78.7 * | | glu-4' | 72.1 | | glu-5' | 78.2 * | | glu-6' | 63.3 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | 2.98 (dd, 13.4, 4.0) | | 07-H | 6.22 (d, 2.2) | | 09-Ha | 3.55 (br t, 9.0) | | 11-Ha | | | 11-He | | | 12-Ha | 2.51 (dt, 13.2, 5.0) | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.42 (q, 10.2) | | 16-Hb | | | 17-H | 2.89 (t, 9.0) | | 18-Me | 1.17 (s ) | | 19-Me | 1.04 (s ) | | 21-Me | 1.56 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.05 (s ) | | 27-Me | 1.14 (s ) | | H-1' | 4.96 (d, 7.6) |
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| M.P. | 276-277 °C | | [α]D15 | + 40.9 ° (c 1.5; MeOH) | | IR (KBr) ν max (cm-1) | 3450 (OH), 1650 | | UV (EtOH) λ max (log ε) | 243 (4.04) |
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| HPTLC | | | TLC | on silica gel, Rf 0.24 (CHCl3-MeOH-H2O 13:7:2) | | GLC | | | HPLC | | | LC | silica gel, solvent CHCl3-MeOH-EtOAc-H2O (2:2:4:1), lower phase |
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Permanent link to this datasheet: PTEROSTERONE 24-O-β-D-GLUCOSIDE
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