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Year of first isolation: |
1992 |
| Formula: | C29H42O8 |
| Molecular weight: | 518 |
| Occurence in plants: |
Ajuga iva [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga iva [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
Ajuga reptans var. reptans [Lamiaceae (alt. Labiatae)] »
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| Canonical SMILES | CC1=C(CC(OC1=O)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C(C)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)([C@H]1CC(=C(C(=O)O1)C)[C@@H](C)O)O)O)C)C » 
| | IUPAC Name | (2R)-4-(1-hydroxyethyl)-2-[(1R)-1-hydroxy-1-[(2S,3R,5R,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]-5-methyl-2,3-dihydropyran-6-one | | CAS-RN | | | PubChem CID | 101635424 | InChiKey
[ ChemIDPlus: search ] | MMGMZHFGVCRNFJ-GNAVUSTCSA-N | | InChI | InChI=1S/C29H42O8/c1-14-16(15(2)30)10-24(37-25(14)34)28(5,35)23-7-9-29(36)18-11-20(31)19-12-21(32)22(33)13-26(19,3)17(18)6-8-27(23,29)4/h11,15,17,19,21-24,30,32-33,35-36H,6-10,12-13H2,1-5H3/t15?,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 536 (M+H+NH3)+, 519 (M+H)+, 501 (M+H-18)+, 483 (M+H-2x18)+, 380 (M+H+ NH3-C22--C29)+, 363 (M+H-C22--C29)+, 345 (M+H-C22--C29-18)+ | | EI-MS m/z (relative intensity %) | | | HR-MS | 519.2539 [M+H]+ |
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| CD3OD | | 01 | 37.5 | | 02 | 68.8 | | 03 | 68.7 | | 04 | 33.0 | | 05 | 51.9 | | 06 | 206.6 | | 07 | 122.4 | | 08 | 167.9 | | 09 | 35.2 | | 10 | 39.4 | | 11 | 21.63 | | 12 | 32.6 | | 13 | 48.8 | | 14 | 85.3 | | 15 | 31.9 | | 16 | 21.7 | | 17 | 50.6 | | 18 | 18.3 | | 19 | 24.5 | | 20 | 76.6 | | 21 | 21.58 | | 22 | 84.4 | | 23 | 25.2 | | 24 | 158.3 | | 25 | 121.0 | | 26 | 169.3 | | 27 | 12.0 | | 28 | 67.0 | | 29 | 21.3 |
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| CD3OD | | 01-Ha | 1.43 (dd, 13.5, 12.4) | | 01-Hb | 1.80 | | 02-Ha | 3.85 (ddd, 12.1, 4.3, 3.3) | | 03-He | 3.96 (q, 2.8) | | 04-Ha | 1.71 | | 04-He | 1.77 | | 05-H | 2.39 (dd, 13.0, 4.5) | | 07-H | 5.82 (d, 2.6) | | 09-Ha | 3.17 (ddd, 11.5, 7.1, 2.6) | | 11-Ha | 1.71 | | 11-He | 1.82 | | 12-Ha | 2.20 (td, 13.1, 5.0) | | 12-He | 1.84 | | 15-Ha | 1.65 | | 15-Hb | 2.01 | | 16-Ha | 1.79 | | 16-Hb | 2.03 | | 17-H | 2.50 | | 18-Me | 0.90 (s) | | 19-Me | 0.97 (s) | | 21-Me | 1.34 (s) | | 22-Hb | 4.14 (dd, 13.5, 3.2) | | 23-Ha | 2.33 (ddq, 18.1, 13.5, 2.5) | | 23-Hb | 2.56 (dd, 18.1, 3.1) | | 27-Me | 1.86 (d, 2.2) | | 28-H | 4.84 (q, 6.6) | | 29-Me | 1.30 (d, 6.6) |
| D2O | | 01-Ha | 1.4 | | 01-Hb | | | 02-Ha | 3.99 (m, w1/2=22) | | 03-He | 4.07 (m, w1/2=8) | | 04-Ha | 1.75 | | 04-He | 1.75 | | 05-H | 2.36 | | 07-H | 5.99 (d, 2.5) | | 09-Ha | 3.12 (m, w1/2=22) | | 11-Ha | 1.7 | | 11-He | 1.8 | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | 1.95 | | 16-Hb | 1.75 | | 17-H | 2.6 | | 18-Me | 0.87 (s) | | 19-Me | 1.00 (s) | | 21-Me | 1.33 (s) | | 22-Hb | 4.34 (dd, 11.5, 4.5) | | 23-Ha | | | 23-Hb | | | 26-Me | 1.83 (sb) | | 28-H | 4.93 (q, 6) | | 29-Me | 1.32 (d, 6) |
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| M.P. | 275-277 °C | | [α]D20 | +7° (c .1, MeOH) | | IR (KBr) ν max (cm-1) | 1695 (a,b-dehydro-d-lactone), 1652 (cyclohexenone); | | UV (EtOH) λ max (log ε) | 243 (4.013) |
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| HPTLC | | | TLC | | | GLC | | | HPLC | 1-Retention time 38.4 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E : 45.6 min); 2-Retention time 15.6 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E: 16.9 min); 3-Retention time 9.8 min [Waters Novapak C18, 100 mm x 8 mm i.d., solvent CH3CN-1? trifluoroacetic acid in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E : 5.7 min) |
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Drosophila melanogaster BII cell assay: EC50 = 7.3 x 10-8M |
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Permanent link to this datasheet: 24-DEHYDROPRECYASTERONE
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