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Year of first isolation: |
1996 |
| Formula: | C29H44O9 |
| Molecular weight: | 536 |
| 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 | | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](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]1C[C@@H]([C@H](C(=O)O1)C)CCO)O)O)C)O)C » 
| | IUPAC Name | (3R,4S,6R)-6-((R)-1-hydroxy-1-((2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-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)ethyl)-4-(2-hydroxyethyl)-3-methyltetrahydro-2H-pyran-2-one | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | YIZXJSNGUYBWSY-PNUXDPGFSA-N | | InChI | InChI=1S/C29H44O9/c1-15-16(7-10-30)11-23(38-24(15)34)27(4,35)21-6-9-28(36)18-12-22(33)29(37)14-20(32)19(31)13-26(29,3)17(18)5-8-25(21,28)2/h12,15-17,19-21,23,30-32,35-37H,5-11,13-14H2,1-4H3/t15-,16+,17+,19+,20-,21+,23-,25-,26-,27-,28-,29-/m1/s1 |
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| MS (thermospray) m/z (relat. intensity %) | 555 (M+H+NH4)+ (17), 554 (M+NH4)+ (42), 537 (M+H)+ (100), 536 (M)+ (82), 519 (M+H-H2O) (54), 501 (M+H-2H2O)+ (11) | | EI-MS m/z (relative intensity %) | |
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| C5D5N | | 01 | 34.8 | | 02 | 67.9 | | 03 | 69.9 | | 04 | 35.9 | | 05 | 79.8 | | 06 | 200.9 | | 07 | 120.0 | | 08 | 166.6 | | 09 | 38.2 | | 10 | 44.8 | | 11 | 22.0 | | 12 | 32.0 | | 13 | 47.9 | | 14 | 83.9 | | 15 | 31.6 | | 16 | 21.1 | | 17 | 49.7 | | 18 | 18.0 | | 19 | 17.1 | | 20 | 76.3 | | 21 | 20.7 | | 22 | 83.5 | | 23 | 28.6 | | 24 | 33.5 | | 25 | 41.0 | | 26 | 174.5 | | 27 | 13.7 | | 28 | 31.1 | | 29 | 60.2 |
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| C5D5N | | 01-Ha | 2.24 | | 01-He | 2.08 | | 02-Ha | 4.24 (m) | | 03-He | 4.18 (m) | | 04-Ha | 2.04 | | 04-He | 1.95 | | 05-H | ? | | 07-H | 6.26 (d, 2.7) | | 09-H | 3.62 (m, w1/2=23) | | 11-Ha | 1.87 | | 11-He | 1.75 | | 12-Ha | 2.58 | | 12-He | 1.90 | | 15-Ha | 2.20 | | 15-Hb | 1.85 | | 16-Ha | 2.35 (m) | | 16-Hb | 2.07 | | 17-H | 2.90 (t, 8.8) | | 18-Me | 1.11 (s) | | 19-Me | 1.16 (s) | | 21-Me | 1.44 (s) | | 22-H | 4.78 (dd, 11.5, 4.5) | | 23-Ha | 2.22 | | 23-Hb | 1.85 | | 24-H | 2.22 | | 25-H | 2.62 | | 27-Me | 1.25 (d, 7.2) | | 28-Ha | 1.83 | | 28-Hb | 1.55 (m) | | 29-Hab | 3.86 (m, w1/2=19, 2H) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3405 (OH), 1714(d-lactone), 1671 (cyclohexenone) | | 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 iPrOH-H2O (13:87), flow-rate 3 mL.min-1, 23°C, Ret 21.2 min. |
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Permanent link to this datasheet: 5,29-DIHYDROXYCAPITASTERONE
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