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(6Z,10Z)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
COSTUNDIDE · costunolid · Costunlide · CUSTUNOLIDE · (3aS,6E,10E,11aR)-6,10-Dimethyl-3-methylene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one · Costulide · NSC 106404 · costunoide
![Molekülstruktur von (6Z,10Z)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one](/img/chemical/5367559.png)
Identifikatoren & physikalische Daten
| CAS No. | 553-21-9 |
|---|---|
| Summenformel | C15H20O2 |
| Durchschnittliche Molmasse | 232,32 g/mol |
| Monoisotopische Masse | 232,14632988 g/mol |
| SMILES | C=C1C(=O)OC2/C=C(/C)CC/C=C(/C)CCC12 |
| InChIKey | HRYLQFBHBWLLLL-GYIATTAWSA-N |
| PubChem CID | 5367559 |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 401 |
| Siedepunkt | 205.00 to 211.00 °C. @ 13.00 mm Hg385.4±42.0 °C(Predicted) |
| Schmelzpunkt | 106 - 107 °C106-107 °C |
| Physical Description | Solid |
| Dichte | 1.03±0.1 g/cm3(Predicted) |
| Lagerbedingungen | -20°C |
| Löslichkeit | DMSO: soluble10mg/mL (clear solution) |
| Aggregatzustand | powder |
| Farbe | white to beige |
| InChI | InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5+,11-9+/t13-,14+/m0/s1 |
| InChIKey | HRYLQFBHBWLLLL-GRFSRWIASA-N |
| SMILES | O1C(=O)C(=C)[C@]2([H])CCC(C)=CCCC(C)=C[C@@]12[H] |t:10,15| |
| LogP (Verteilungskoeffizient) | 4.049 (est) |
| CAS Datenbank | 553-21-9(CAS DataBase Reference) |
| NIST chemische Informationen | Germacra-1(10),4,11(13)-trien-12-oic acid, 6«alpha»-hydroxy-, «gamma»-lactone, (e,e)-(553-21-9) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| Zollcode | 29322090 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Skin Sens. 1 |
Anwendungen & Verwendung
Beschreibung
Costunolide is a germacranolide sesquiterpene lactone extracted from costus oil. With alantolactone and dehydrocostuslactone, it is a component of lactone mix used to elicit reactions in Compositae-sensitive patients. An erythema-multiform-like occupational contact dermatitis case occurred in a chemistry student after accidental exposure to costus oil (CJ Le Coz & JP Lepoittevin, unpublished results).
Verwenden
Costunolide is the oil extracted from Saussurea lappa is used in perfumery and in the Orient for all kinds of diseases.