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Year of first isolation: |
1990 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Silene nutans [Caryophyllaceae] »  ![Wikipedia: Silene nutans [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(C(C(C(C4)O)O)O)C)C1(CCC2C(C)(CCCC(C)(C)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | [C@@H]1([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)(CCCC(C)(C)O)O)O)C)C)O » 
| | IUPAC Name | (1S,2R,3R,5R,9R,10R,13R,14S,17S)-17-[(2S)-2,6-dihydroxy-6-methylheptan-2-yl]-1,2,3,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 70691108 | InChiKey
[ ChemIDPlus: search ] | MXVMNRFIIZOGBE-WKJDFDCFSA-N | | InChI | InChI=1S/C27H44O7/c1-23(2,32)9-6-10-25(4,33)20-8-12-27(34)16-13-18(28)17-14-19(29)21(30)22(31)26(17,5)15(16)7-11-24(20,27)3/h13,15,17,19-22,29-34H,6-12,14H2,1-5H3/t15-,17-,19+,20-,21+,22+,24+,25-,26+,27+/m0/s1 |
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| CI-MS(NH3) m/z | 498 (MH + NH3)+, 481 (MH)+, 463, 445, 427, 391, 363, 345 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| CD3OD | | 01 | 76.6 | | 02 | 68.6 | | 03 | 71.1 | | 04 | 33.7 | | 05 | 46.9 | | 06 | 205.8 | | 07 | 122.3 | | 08 | 167.5 | | 09 | 35.8 | | 10 | 43.9 | | 11 | 22.0 | | 12 | 32.5 | | 13 | 48.2 | | 14 | 87.5 | | 15 | 31.8 | | 16 | 22.0 | | 17 | 53.6 | | 18 | 18.3 | | 19 | 20.2 | | 20 | 76.1 | | 21 | 26.6 | | 22 | 46.0 | | 23 | 20.3 | | 24 | 45.6 | | 25 | 71.6 | | 26 | 29.3 | | 27 | 29.5 |
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| D2O | | 01-He | 3.92 (m, w1/2=7) | | 02-Ha | 4.03 (t, 3.2) | | 03-He | 4.15 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | 2.62 (t-like ) | | 07-H | 6.00 (d, 1.5) | | 09-Ha | 3.04 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.30 (m ) | | 18-Me | 0.83 (s ) | | 19-Me | 1.09 (s ) | | 21-Me | 1.30 (s ) | | 22-Ha | | | 22-Hb | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.22 (s ) | | 27-Me | 1.22 (s ) |
| CD3OD | | 01-He | 3.82 (s, br) | | 02-Ha | 3.87 (t, 3.0) | | 03-He | 4.04 (s, br) | | 04-Ha | 1.76* | | 04-He | 1.81* | | 05-H | 2.61 (dd, 12.7, 4.6) | | 07-H | 5.84 (d, 2.4) | | 09-Ha | 3.08 (m, br) | | 11-Ha | 1.69 | | 11-He | 1.74 | | 12-Ha | 2.09 | | 12-He | 1.83 | | 15-Ha | 1.61 | | 15-Hb | 1.97 | | 16-Ha | 1.88 | | 16-Hb | 1.92 | | 17-H | 2.33 (t, 9.1) | | 18-Me | 0.87 (s) | | 19-Me | 1.08 (s) | | 21-Me | 1.27 (s) | | 22-H | 1.51 | | 22-Hb | 1.51 | | 23-Ha | 1.40 | | 23-Hb | 1.43 | | 24-Ha | 1.43 | | 24-Hb | 1.43 | | 26-Me | 1.19 (s) | | 27-Me | 1.19 (s) |
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| M.P. | | | [α]D20 | + 80 (c 0.1; MeOH) | | IR (KBr) ν max (cm-1) | 3430, 3300, 1645 | | UV (EtOH) λ max (log ε) | 206 (1.8), 242 (4.205) |
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| HPTLC | | | TLC | | | GLC | | | HPLC | NP-HPLC, Retention time 13.8 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 : 16.8 min); Retention time 32.8 min [ Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min) |
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Permanent link to this datasheet: 22-DEOXYINTEGRISTERONE A
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