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Year of first isolation: |
1992 |
| Formula: | C19H26O6 |
| Molecular weight: | 350 |
| Occurence in plants: |
Serratula tinctoria [Asteraceae] »  ![Wikipedia: Serratula tinctoria [Asteraceae]](/images/wikipedia.png)
Polypodium vulgare [Polypodiaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C1(CCC2=O)O | 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(CCC2=O)O)C)O)C » 
| | IUPAC Name | (2S,3R,5S,9R,10R,13S,14R)-2,3,5,14-tetrahydroxy-10,13-dimethyl-2,3,4,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthrene-6,17-dione | | CAS-RN | | | PubChem CID | 101642416 | InChiKey
[ ChemIDPlus: search ] | OEJRYBSXPXGVNX-LWZFRQFWSA-N | | InChI | InChI=1S/C19H26O6/c1-16-5-3-10-11(18(16,24)6-4-14(16)22)7-15(23)19(25)9-13(21)12(20)8-17(10,19)2/h7,10,12-13,20-21,24-25H,3-6,8-9H2,1-2H3/t10-,12-,13+,16+,17+,18+,19+/m0/s1 |
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| CI-MS (NH3) m/z | 368 (M+H+NH3)+, 351, 333, 315, 245 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| CD3OD | | 01 | 34.3 | | 02 | 68.5 | | 03 | 70.3 | | 04 | 36.3 | | 05 | 80.6 | | 06 | 202.2 | | 07 | 121.2 | | 08 | 164.4 | | 09 | 39.8 | | 10 | 45.7 | | 11 | 21.8 | | 12 | 25.2 | | 13 | 54.2 | | 14 | 80.4 | | 15 | 29.2 | | 16 | 34.1 | | 17 | 220.0 | | 18 | 17.7 | | 19 | 17.3 | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| CD3OD | | 01-Ha | 1.74 | | 01-Hb | 1.74 | | 02-Ha | 3.94 (ddd, 8.7, 8.3, 3.3) | | 03-He | 4.00 (q, 3.1) | | 04-Ha | 2.07 (dd, 14.8, 3.0) | | 04-He | 1.80 | | 05-H | | | 07-H | 5.97 (d, 2.8) | | 09-Ha | 3.22 (ddd, 11.5, 6.9, 2.8) | | 11-Ha | 1.71 (ddd, 11.6, 13.6, 4.9) | | 11-He | 1.92 (dddd, 13.6, 6.7, 4.6, 2.1) | | 12-Ha | 2.13 (td, 13.2, 4.8) | | 12-He | 1.59 (ddd, 13.0, 4.9, 2.0) | | 15-Ha | 2.30 | | 15-Hb | 2.02 | | 16-Ha | 2.36 | | 16-Hb | 2.51 | | 17-H | | | 18-Me | 0.88 (s) | | 19-Me | 0.94 (s) | | 20-H | | | 21-Me | | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | | | 27-Me | |
| CD3OD | | 01-Ha | 1.6 (dd 3, 13) | | 01-Hb | 2.1 | | 02-Ha | 3.93 (ddd 3, 3, 12) | | 03-He | 4.0 (q 3.05) | | 04-Ha | 2.08 | | 04-He | 1.8 | | 05-H | | | 07-H | 5.97 (d 2.5) | | 09-Ha | 3.2 (m, w 1/2 = 22) | | 11-Ha | 1.7 | | 11-He | 1.9 | | 12-Ha | 2.1 | | 12-He | 1.6 | | 15-Ha | 2.4 | | 15-Hb | 2.05 | | 16-Ha | 2.25 | | 16-Hb | 2.5 | | 17-H | | | 18-Me | 0.88 (s) | | 19-Me | 0.95 (s) | | 20-H | | | 21-Me | | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | | | 27-Me | |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| RP-HPLC | Ret 5.1 min (Column Spherisorb-5ODS2, 25 cm x 4.6 mm i.d., solvent ACN : 1? TFA in H2O 23:77 v/v, flow-rate 1ml.min-1) (20E 5.2 min) | | TLC | | | GLC | | | NP-HPLC | Ret 16.1 min (Column Zorbax-Sil, 25 cm x 4.6 mm i.d., solvent isoC8-iPrOH-H2O, 100:30:2 v/v/v, flow-rate 1ml.min-1) (20E 22.6 min) |
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Permanent link to this datasheet: 5β-HYDROXYRUBROSTERONE
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