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Year of first isolation: |
1970 |
| Formula: | C27H46O6 |
| Molecular weight: | 466 |
| Occurence in plants: |
Cheilanthes tenuifolia [Pteridaceae] »  ![Wikipedia: Cheilanthes tenuifolia [Pteridaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)CC1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,8R,9S,10R,13R,14R,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 26152-93-2 | | PubChem CID | 101297731 | InChiKey
[ ChemIDPlus: search ] | MSFNGOWODGGQNW-YZENLCTGSA-N | | InChI | InChI=1S/C27H46O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h15-20,22-23,28,30-33H,6-14H2,1-5H3/t15-,16+,17-,18+,19-,20+,22+,23-,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 448 (M-18)+, 430, 412, 394, 379, 332, 302, 99, 81 | | 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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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-Ha | | | 07-He | | | 08-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.83 (s ) | | 19-Me | 1.01 (s ) | | 21-Me | 1.24 (d, 6) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.36 (s ) | | 27-Me | 1.36 (s ) |
| CDCl3 (2,3,22-triOAc) | | 01-Ha | | | 01-Hb | | | 02-Ha | 5.35 (w1/2 = 8) | | 03-He | ~ 5.10 (w1/2 > 16) | | 04-Ha | | | 04-He | | | 05-H | | | 07-Ha | | | 07-He | | | 08-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.80 | | 19-Me | 0.96 | | 21-Me | ~ 0.94 (w1/2 > 16) | | 22-H | ~ 4.9 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.24 | | 27-Me | 1.24 | | acetates | 2.00, 2.05, 2.09 |
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| M.P. | 235-238 °C | | [α]D20 | | | IR (KBr) ν max (cm-1) | 1684 (carbonyl) | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC on silica | Rf 0.20 (CHCl3-96% EtOH 4:1) identical to that of ecdysone | | GLC | | | HPLC | |
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Permanent link to this datasheet: CHEILANTHONE A
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