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Year of first isolation: |
1964 |
| Formula: | C27H44O2 |
| Molecular weight: | 400 |
| Occurence in plants: |
Wilcoxia viperina [Cactaceae] »  ![Wikipedia: Wilcoxia viperina [Cactaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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![DEOXYVIPERIDONE [= 5α-KETOL]](images/ecdy/186.gif)
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| Canonical SMILES | CC(C)CCCC(C)C1CCC2C1(CCC3C2=CC(=O)C4C3(CCC(C4)O)C)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2(C1CC[C@@H]2[C@H](C)CCCC(C)C)C)C » 
C1[C@]2([C@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)C »
C1[C@]2([C@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)C »
| | IUPAC Name | (3S,5S,9R,10R,13R,14R,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 10938235 | InChiKey
[ ChemIDPlus: search ] | AVFLDWQHIWZEHL-DYRJEOCBSA-N | | InChI | InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h16-19,21-24,28H,6-15H2,1-5H3/t18-,19+,21-,22+,23+,24-,26-,27-/m1/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | | | 19-Me | | | 20-H | | | 21-Me | | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | | | 27-Me | |
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| M.P. | 195-197 °C | | [α]D26 | + 3.6 ° (c ; CDCl3) | | IR (KBr) ν max (cm-1) | ?(OH), 1675 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 245 (4.130) |
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| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC, column Spherisorb 5-ODS-2, solvent linear gradient (in 30 min) of 20% to 100% ACN-iPrOH (5:2) in 0.1% TFA in water, flow-rate 1 ml.min-1, Rt 41.1 min (2dE : 17.0 min, 39.9 min for the 5beta isomer). |
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| General | HARVEY, W.E. et al. (1961) Chem. Ind. (London) 18, 595-596 |
 | | General | HARTSHORN, M.P. et al. (1962) J. Chem. Soc., 3839-3841 |
| | First isolation | DJERASSI, C. et al. (1964) Chem. Ber. 97, 3118-3130 |
| | General | HOFFMEISTER, H. et al. (1965) Chem. Ber. 98, 2361-2375 |
| | General | SLAYTOR, M. et al. (1965) J. Biol. Chem. 240, 4598-4602 |
| | General | GALBRAITH, M.N. et al. (1974) Aust. J. Chem. 27, 1087-1095 |
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Permanent link to this datasheet: DEOXYVIPERIDONE [= 5α-KETOL]
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