1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-on

Damascenone

HCID 62775CAS 23696-85-7

Teilstruktursuche Ähnliche Strukturen suchen

Grundinformationen

Standard-SMILES: CC=CC(=O)C1=C(C)C=CCC1(C)C
InChIKey: POIARNZEYGURDG-UHFFFAOYSA-N
Summenformel: C13H18O
Durchschnittliche Molmasse: 190,28 g/mol
Monoisotopische Masse: 190,1357652

Überblick

(E/Z)-damascenone has been reported in Centaurea armena, Iris × germanica, and other organisms with data available.

Namen und Bezeichner

Bevorzugter Name: Damascenone
IUPAC: 1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
Lokaler Name: 1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-on
Englischer Name: Damascenone
Summenformel: C13H18O
Molmasse: 190.28

Namen und Synonyme

DTXSID6041397DTXCID80196511RefChem:919620Damascenoneb-damascenone2,6,6-Trimethyl-1-crotonyl-1,3-cyclohexadiene1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-; 1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; 1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-buten-1-one; 1-Crotonoyl-2,6,6-trimethyl-1,3-cyclohexadiene; 2,6,6-Trimethyl-1-(2-butenoyl)-1,3-cyclohexadiene; 2,6,6-Trimethyl-1-crotonyl-1,3-cyclohexadieneSCHEMBL164856orb1222483POIARNZEYGURDG-UHFFFAOYSA-N1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; 1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-buten-1-one; 1-Crotonoyl-2,6,6-trimethyl-1,3-cyclohexadiene; 2,6,6-Trimethyl-1-(2-butenoyl)-1,3-cyclohexadiene

Weitere Namen anzeigen

β-Damascenone2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-DAMASCENONE TOTALFEMA 34201-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-Buten-1-one4-(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-oneDamasioneDAMASCENONTrimethyl cyclohexadienyl butenone

s6431AKOS028110970DB-336645NS00075807(E)-beta-Damascenone 1000 microg/mL in Acetonitrile2,6,6-trimethyl-1-(but-2-enoyl)-cyclohexa-1,3-dien1-(2,6,6-trimethylcyclohexa-1,3-dienyl) but-2-en-1one1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)-2-buten-1-one

Datenbank-Bezeichner

CAS: 23696-85-7
PubChem CID: 62775
DTXSID: DTXSID6041397

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,2
Polarare Oberfläche (TPSA): 17,1 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 1
Frei drehbare Bindungen: 2
Schwere Atome: 14
Formalladung: 0
Komplexität: 327

Physikochemische Eigenschaften

Siedepunkt: 275.6 · 275.6±10.0 °C(Predicted)
Dichte: 0.8 · 0.800-0.830 g/mL at 25 °C (lit.)
Brechungsindex: 1.35 · 1.350-1.380
FEMA: 3420 · 3420 | 1-(2,6,6-TRIMETHYLCYCLOHEXA-1,3-DIENYL)-2-BUTEN-1-ONE
Flammpunkt: 62 °F · 62°F
storage temp.: 2 · 2-8°C
Löslichkeit: Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand: liquid
Farbe: yellow
Geruch (Odor): 10 % · at 10.00 % in dipropylene glycol. natural sweet fruity rose plum grape raspberry sugar
Geruchsart: floral
JECFA Number: 387 · 387
Stabilität: Light Sensitive
Major Application: 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: 4.04 · 4.04
CAS Datenbank: 23696 · 23696-85-7(CAS DataBase Reference)
NIST chemische Informationen: 2 · 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-(23696-85-7)
EPA chemische Informationen: 2 · 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)- (23696-85-7)

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk: 3
tsca: TSCA listed
ridadr: UN 1170
hs_code: 33021090
risk_code: 11-43
hazard_code: F,Xi
safety_code: 7-16-36/37
Speicherklasse: 10 - Combustible liquids
Hazard Classifications: Aquatic Chronic 2Skin Sens. 1

Chemie und Industrie

Verwendung und Herstellung

Use ClassificationFlavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Anwendungen · 2 Einträge

OccurrenceReported 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.

VerwendenDamascenone 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.

Darstellung

synthetischeBy 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.