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Year of first isolation: |
1971 |
Formula: | C29H44O8 |
Molecular weight: | 520 |
Occurence in plants: |
Cyathula capitata [Amaranthaceae] » ![Wikipedia: Cyathula capitata [Amaranthaceae]](/images/wikipedia.png)
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Occurence in animals: |
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Canonical SMILES | CC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)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](C[C@H]1[C@@H](C(=O)O[C@@H]1C)C)O)O)O)C)C » 
| IUPAC Name | (3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,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]butyl]-3,5-dimethyloxolan-2-one | CAS-RN | 31581-82-5 | PubChem CID | 12305322 | InChiKey [ ChemIDPlus: search ] | NEFYSBQJYCICOG-SAGHCZLLSA-N | InChI | InChI=1S/C29H44O8/c1-14-16(15(2)37-25(14)34)10-24(33)28(5,35)23-7-9-29(36)18-11-20(30)19-12-21(31)22(32)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19+,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1 |
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CI-MS (NH3) m/z | | EI-MS m/z (relative intensity %) | 520 (M)+, ..., 363, 345, 327, 201, 183, 157, 113 | 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 | | 28 | | 29 | |
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CDCl3 (2,3,22-triOAc) | 01-Ha | | 01-He | | 02-Ha | ~ 5.20 | 03-He | ~ 4.68 | 04-Ha | | 04-He | | 05-H | | 07-H | 5.82 (d ) | 09-Ha | | 11-Ha | | 11-He | | 12-Ha | | 12-He | | 15-Ha | | 15-Hb | | 16-Ha | | 16-Hb | | 17-H | | 18-Me | 0.85 (s ) | 19-Me | 0.98 (s ) | 21-Me | 1.26 (s ) | 22-H | ~ 4.88 | 23-Ha | | 24-Ha | | 24-Hb | | 25-H | | 26-Me | -- | 27-Me | 1.31 (d ) | 28-H | ~ 4.15 | 29-Me | 1.42 (d ) |
C5D5N (free) | 01-Ha | | 01-He | | 02-Ha | | 03-He | | 04-Ha | | 04-He | | 05-H | | 07-H | 6.26 (d ) | 09-Ha | | 11-Ha | | 11-He | | 12-Ha | | 12-He | | 15-Ha | | 15-Hb | | 16-Ha | | 16-Hb | | 17-H | | 18-Me | 1.23 (s ) | 19-Me | 1.41 (s ) | 21-Me | 1.57 (s ) | 22-H | | 23-Ha | | 24-Ha | | 24-Hb | | 25-H | | 26-Me | -- | 27-Me | 1.35 (d ) | 28-H | | 29-Me | 1.39 (d ) |
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M.P. | 274-275°C | [α]D20 | + 116 ° (c ; MeOH) | IR (KBr) ν max (cm-1) | 1750 (gama-lactone), 1658 | UV (MeOH) λ max (log ε) | 242 (?) |
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Permanent link to this datasheet: EPICYASTERONE [cf. 5-EPI-CYASTERONE]
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