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Year of first isolation: |
2001 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Vitex cymosa [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Vitex cymosa [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(CCC(C(C)(CO)O)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)(CCC(C(CO)(C)O)O)O)O)C)C » 
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)(CC[C@H]([C@](CO)(C)O)O)O)O)C)C »
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)(CC[C@H]([C@@](CO)(C)O)O)O)O)C)C »
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)(CC[C@@H]([C@](CO)(C)O)O)O)O)C)C »
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)(CC[C@@H]([C@@](CO)(C)O)O)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2S)-2,5,6,7-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 152755867 | InChiKey
[ ChemIDPlus: search ] | ZHWWWLBWFJXRQS-NSPYQFHBSA-N | | InChI | InChI=1S/C27H44O8/c1-23-13-20(31)19(30)12-17(23)18(29)11-16-15(23)5-8-24(2)21(6-10-27(16,24)35)25(3,33)9-7-22(32)26(4,34)14-28/h11,15,17,19-22,28,30-35H,5-10,12-14H2,1-4H3/t15-,17-,19+,20-,21-,22?,23+,24+,25-,26?,27+/m0/s1 |
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| HR-MS | | | EI-MS m/z (relative intensity %) | 460 (1), 442 (5), 363 (5), 345 (12), 327 (11), 301 (8), 285 (5), 267 (8), 259 (5), 225 (6), 211 (6), 173 (10), 129 (9), 115 (36), 105 (8), 97 (18), 91 (10), 69 (34), 55 (25), 43 (100) | | FAB-MS m/z (relative intensity %) | 519 (100), 497 (31), 460 (60), 385 (34), 363 (48), 301 (18) |
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| C5D5N | | 01 | 37.8 | | 02 | 67.9 | | 03 | 67.8 | | 04 | 32.3 | | 05 | 51.2 | | 06 | 203.3 | | 07 | 121.4 | | 08 | 166.0 | | 09 | 34.2 | | 10 | 38.5 | | 11 | 20.9 | | 12 | 31.8 | | 13 | 47.9 | | 14 | 84.0 | | 15 | 31.6 | | 16 | 21.3 | | 17 | 49.9 | | 18 | 17.7 | | 19 | 24.3 | | 20 | 76.7 | | 21 | 21.5 | | 22 | 37.4 | | 23 | 26.5 | | 24 | 77.5 | | 25 | 71.4 | | 26 | 64.6 | | 27 | 24.5 |
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| C5D5N (2 epimers) | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.25 | | 03-He | 4.25 | | 04-Ha | | | 04-He | | | 05-H | 3.02 (dd, 13, 4) | | 07-H | 6.28 (d, 1.7) | | 09-Ha | 3.69 (m) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.07 (t, 9) | | 18-Me | 1.24 (s) | | 19-Me | 1.08 (s) | | 21-Me | 1.59 (s), 1.60 (s) | | 22-Ha | | | 22-Hb | | | 23-Ha | | | 23-Hb | | | 24-H | 3.89 (br dd, 10, 3) | | 26-CH2OH | 4.25 | | 27-Me | 1.49 (s), 1.50 (s) |
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| M.P. | - °C | | [α]D25 | + 36.0 ° (c 1%; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPLC | RP-HPLC column Lichrosorb RP-18, 5 ?m, 4 mm i.d., 250 mm long, solvent MeOH-H2O 30:70, flow-rate 1.2 ml.min-1, Ret 8.24 and 8.59 min (2 isomers). | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 26-HYDROXYPINNATASTERONE
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