1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-on
β-Damascenone · 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)- · DAMASCENONE TOTAL · FEMA 3420 · 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-Buten-1-one · 4-(2,6,6-Trimethyl cyclohexa-1,3-dienyl)but-2-en-4-one · (E)-1-(2,6,6-triMethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one · Damasione
Identifikatoren & physikalische Daten
| CAS No. | 23696-85-7 |
|---|---|
| Summenformel | C13H18O |
| Durchschnittliche Molmasse | 190,28 g/mol |
| Monoisotopische Masse | 190,1357652 g/mol |
| SMILES | CC=CC(=O)C1=C(C)C=CCC1(C)C |
| InChIKey | POIARNZEYGURDG-UHFFFAOYSA-N |
| PubChem CID | 62775 |
| DTXSID | DTXSID6041397 |
| Lokaler Name | 1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-on |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 327 |
| Siedepunkt | 275.6±10.0 °C(Predicted) |
| Dichte | 0.800-0.830 g/mL at 25 °C (lit.) |
| Brechungsindex | 1.350-1.380 |
| FEMA | 3420 | 1-(2,6,6-TRIMETHYLCYCLOHEXA-1,3-DIENYL)-2-BUTEN-1-ONE |
| Flammpunkt | 62°F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly) |
| Aggregatzustand | liquid |
| Farbe | yellow |
| Geruch | at 10.00 % in dipropylene glycol. natural sweet fruity rose plum grape raspberry sugar |
| Geruchsart | floral |
| JECFA Number | 387 |
| Stabilität | Light Sensitive |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMINGFRAGRANCE |
| InChI | 1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ |
| InChIKey | POIARNZEYGURDG-FNORWQNLSA-N |
| SMILES | C\C=C\C(=O)C1=C(C)C=CCC1(C)C |
| LogP (Verteilungskoeffizient) | 4.04 |
| CAS Datenbank | 23696-85-7(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-(23696-85-7) |
| EPA chemische Informationen | 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)- (23696-85-7) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1170 |
| Zollcode | 33021090 |
| R-Sätze (R) | 11-43 |
| Gefahrensymbole | F,Xi |
| Sicherheitshinweise (S) | 7-16-36/37 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrenklasse | Aquatic Chronic 2Skin Sens. 1 |
Anwendungen & Verwendung
Occurrence
Reported found in raspberry oil, Burley tobacco, apple, lemon balm, summer savory, anise, hyssop, apple juice, cooked apple, apricot, sweet and sour cherry, black currant berries, fresh blackberry, strawberry jam, hop oil rum, white wine, red wine, black tea, tomato, rye bread, blue cheese, cow, goat and sheep milk, hop oil, beer, cognac, rum, whiskies, scotch, cider, grape wines, coffee, tea, popcorn, oatmeal, soybean, plum, prune, beans, starfruit, mango, tamarind, dill seed, corn oil, okra, cape gooseberry, anise hyssop and Roman chamomile oil.
Verwenden
Damascenone is a fragrance ingredient that can be used in shampoos, fine fragrances, decorative cosmetics, toilet soaps as well as non-cosmetic products like household cleaners and detergents.
Herstellung & Synthese
synthetische
By treating the corresponding ethyl safranate with allyl lithium, followed by catalytic isomerization of the reaction product; also from the oxirane derivative of β-damascone by an acid-catalyzed reaction.