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Year of first isolation: |
1995 |
| Formula: | C28H40O4 |
| Molecular weight: | 440 |
| Occurence in plants: |
Calvatia cyathiformis [Fungi] »  ![Wikipedia: Calvatia cyathiformis [Fungi]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C)C(C)C=CC(C)C1CCC2(C1(CCC3(C2=CC(=O)C4=CC(=O)CCC43C)O)C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2(C(=CC(=O)C1)C(=O)C=C1[C@@]2(CC[C@]2([C@]1(CC[C@@H]2[C@H](C)/C=C/[C@@H](C(C)C)C)O)C)O)C » 
| | IUPAC Name | (9S,10S,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-9,14-dihydroxy-10,13-dimethyl-2,11,12,15,16,17-hexahydro-1H-cyclopenta[a]phenanthrene-3,6-dione | | CAS-RN | 162857-86-5 | | PubChem CID | 11743978 | InChiKey
[ ChemIDPlus: search ] | PPPHAARYIMWGSU-VWLVVCIOSA-N | | InChI | InChI=1S/C28H40O4/c1-17(2)18(3)7-8-19(4)21-10-12-27(31)24-16-23(30)22-15-20(29)9-11-25(22,5)28(24,32)14-13-26(21,27)6/h7-8,15-19,21,31-32H,9-14H2,1-6H3/b8-7+/t18-,19+,21+,25-,26+,27+,28+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 440.2932 [M]+ (4), C28H40O4 requires 440.2926, 422 [M - H2O] + (38), 297 (26), 229 (87). | | HR-MS | |
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| CDCl3 | | 01 | 27.7 | | 02 | 34.3 | | 03 | 200.1 | | 04 | 125.5 | | 05 | 155.4 | | 06 | 188.1 | | 07 | 129.1 | | 08 | 163.4 | | 09 | 74.4 | | 10 | 44.1 | | 11 | 27.6 | | 12 | 27.7 | | 13 | 46.4 | | 14 | 87.0 | | 15 | 31.9 | | 16 | 26.3 | | 17 | 50.2 | | 18 | 16.4 | | 19 | 22.9 | | 20 | 40.0 | | 21 | 21.3 | | 22 | 135.4 | | 23 | 133.4 | | 24 | 43.0 | | 25 | 33.2 | | 26 | 20.0 | | 27 | 19.7 | | 28 | 17.7 |
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| CDCl3 | | 01-Ha | 2.79 (ddd, 5.1, 13.9, 13.9) | | 01-Hb | 1.82 (br d, 13.9) | | 02-Ha | 2.59 (ddd, 4.0, 5.1, 16.8) | | 02-Hb | 2.50 (ddd, 5.5, 13.9, 16.8) | | 04-H | 6.60 (s) | | 07-H | 6.19 (s) | | 11-Ha | 2.09 (m) | | 11-Hb | 1.83 (m) | | 12-Ha | 2.18 (ddd, 4.4, 13.2, 13.6) | | 12-He | 1.75 (br d, 13.6) | | 15-Ha | 1.97 (m) | | 15-Hb | 1.65 (m) | | 16-Ha | 1.94 (m) | | 16-Hb | 1.46 (m) | | 17-H | 2.01 (m) | | 18-Me | 0.77 (s) | | 19-Me | 1.37 (s) | | 20-H | 2.11 (m) | | 21-Me | 1.05 (d, 6.6) | | 22-H | 5.20 (dd, 8.4, 15.0) | | 23-H | 5.29 (dd, 7.7, 15.0) | | 24-H | 1.88 (m) | | 25-H | 1.49 (m) | | 26-Me | 0.84 (d, 6.9) | | 27-Me | 0.85 (d, 6.9) | | 28-Me | 0.93 (d, 6.9) | | OH-14 or 9 | 4.22 (1H,br s) | | OH-9 or 14 | 2.46 (1H,br s) |
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| M.P. | 173-175 °C ; | | [α]D20 | - 103 ? ° (c 0.27; CHCl3) | | IR (KBr) ν max (cm-1) | 3450 (OH), 1660 (CO) | | UV (MeOH) λ max (log ε) | 266 (4.09) ; |
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Permanent link to this datasheet: CALVASTEROL B
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