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Year of first isolation: |
1996 |
| Formula: | C29H38O8 |
| Molecular weight: | 514 |
| Occurence in plants: |
Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CCC1=C(C(=O)OC(C1)C(C)(C2CCC3(C2(C(=O)CC4C3=CC(=O)C5C4(CC(C(=O)C5)O)C)C)O)O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](CC(=O)[C@H]1O)C(=O)C=C1[C@@H]2CC(=O)[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H]1CC(=C(C(=O)O1)C)CC)O)O)C)C » 
| | IUPAC Name | (2S,10R,13R,14R,17S)-17-[1-(4-ethyl-5-methyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-2,14-dihydroxy-10,13-dimethyl-2,4,5,9,11,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,6,12-trione | | CAS-RN | | | PubChem CID | 11272278 | InChiKey
[ ChemIDPlus: search ] | XESXXIRWMOUPNF-UGYOQYKUSA-N | | InChI | InChI=1S/C29H38O8/c1-6-15-9-24(37-25(34)14(15)2)28(5,35)22-7-8-29(36)17-10-19(30)18-11-20(31)21(32)13-26(18,3)16(17)12-23(33)27(22,29)4/h10,16,18,21-22,24,32,35-36H,6-9,11-13H2,1-5H3/t16?,18?,21-,22-,24?,26+,27-,28?,29+/m0/s1 |
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| CI-MS (NH3) m/z | | | MS (thermospray) m/z (relat. intensity %) | 532 (M+NH4)+ (77), 515 (M+H)+ (56), 514 (M)+ (100), 497 M+H-H2O) (62) |
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| C5D5N | | 01 | 38.5 | | 02 | 71.7 | | 03 | 209.7 | | 04 | 45.4 | | 05 | 57.5 | | 06 | 198.2 | | 07 | 122.5 | | 08 | 166.8 | | 09 | 37.4 | | 10 | 39.9 | | 11 | 36.8 | | 12 | 208.4 | | 13 | 61.7 | | 14 | 89.1 | | 15 | 32.0 | | 16 | 21.0 | | 17 | 43.9 | | 18 | 17.4 | | 19 | 22.1 | | 20 | 74.9 | | 21 | 22.1 | | 22 | 83.1 | | 23 | 30.1 | | 24 | 154.2 | | 25 | 121.2 | | 26 | 163.1 | | 27 | 12.2 | | 28 | 27.1 | | 29 | 11.5 |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 4.87 (m) | | 03-He | ? | | 04-Ha | | | 04-He | | | 05-H | 2.78 (dd, 13.4, 5.5) | | 07-H | 6.41 (d, 2.7) | | 09-H | 4.41 (m, w1/2=23) | | 11-Hab | 3.01 (cs, 2H) | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.51 (t, 8.6) | | 18-Me | 1.55 (s) | | 19-Me | 1.19 (s) | | 21-Me | 1.70 (s) | | 22-H | 4.46 (dd, 12.9, 3.3) | | 23-Ha | 2.44 | | 23-Hb | 2.23 (m) | | 25-H | ? | | 27-Me | 1.87 (s) | | 28-Ha | 1.87 | | 29-Me | 0.67 (t, 7.5) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3427 (OH), 1750-1600 (broad band) | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC, column Tracer 30x0.78 cm packed with Spherisorb-ODS2 10?m, solvent ACN-H2O (20:80), flow-rate 3 mL.min-1, 23°C, Ret 36.9 min. |
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Permanent link to this datasheet: 3-DEHYDROAJUGALACTONE
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