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Year of first isolation: |
1983 |
| Formula: | C27H42O8 |
| Molecular weight: | 494 |
| Occurence in plants: |
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| Occurence in animals: |
metabolite formed by Carcinus maenas [Crustaceae] »  ![Wikipedia: metabolite formed by Carcinus maenas [Crustaceae]](/images/wikipedia.png)
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| Canonical SMILES | CC(CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(=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)([C@@H](CCC(C(=O)[O-])C)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)([C@@H](CC[C@@H](C(=O)[O-])C)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)([C@@H](CC[C@@H](C(=O)[O-])C)O)O)O)C)C »
| | IUPAC Name | (5R,6S)-5,6-dihydroxy-2-methyl-6-[(2S,3R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanoic acid | | CAS-RN | | | PubChem CID | 11306484 | InChiKey
[ ChemIDPlus: search ] | YXNVOFMJAJIRAC-SSZMODRESA-N | | InChI | InChI=1S/C27H42O8/c1-14(23(32)33)5-6-22(31)26(4,34)21-8-10-27(35)16-11-18(28)17-12-19(29)20(30)13-24(17,2)15(16)7-9-25(21,27)3/h11,14-15,17,19-22,29-31,34-35H,5-10,12-13H2,1-4H3,(H,32,33)/t14?,15?,17?,19-,20+,21+,22-,24-,25-,26+,27-/m1/s1 |
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| CI-MS (NH3) (methyl ester) m/z | 509 (M+H)+, 494, 491, 477, 473, 459, 441, 363, 345 | | EI-MS m/z | 458 (M - 2x18)+, 157, 113, 87, 58 | | 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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| D2O | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.0986 (s ) | | 19-Me | 0.9566 (s ) | | 21-Me | 1.3110 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | -- | | 27-Me | 1.1871 (d ) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3450 (OH), 2940, 2870 (CH3, CH2), 1660 (cyclohexenone) | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC, Retention time 25.5 min and 30.2 min (2 isomers, 25R and25S) [column Ultrasphere-ODS, 25 cm long, 4.6 mm i.d., solvent ACN-20 mM Tris/HClO4, pH 7.5, 8:92 v/v, flow-rate 1 ml.min-1]. |
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| General | SPINDLER, K.-D. et al. (1976) Steroids 27, 553-565 |
 | | First isolation | ENDERLE, U. et al. (1983) (Dissertation, Marburg, FRG), |
| | General | LAFONT, R. et al. (1983) Arch. Insect Biochem. Physiol. 1, 41-58 |
| | General | LACHAISE, F. et al. (1984) Steroids 43, 243-259 |
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Permanent link to this datasheet: 25-DEOXY-20-HYDROXYECDYSONOIC ACID
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