57378-68-4

Basic information

• Product Name: 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one
• Synonyms: 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one;delta-1-(2,6,6-Trimethyl-3-cyclohexen-1-yl)-2-buten-1-one;2-Buten-1-one, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-;(E)-1-(2,6,6-TRIMETHYL-1-CYCLOHEX-3-ENYL)BUT-2-EN-1-ONE;1-(2,6,6-TRIMETHYL-3-CYCLOHEXEN-1-YL)-2-BUTEN-1-ONE.DELTA.-DAMASCONE;a-Damascone
• CAS NO: 57378-68-4
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.2973
• EINECS: 260-709-8
• Mol File: 57378-68-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 263.6 °C at 760 mmHg
• Flash Point: 103.7 °C
• Appearance: /
• Density: 0.89 g/cm³
• Vapor Pressure: 0.0102mmHg at 25°C
• Refractive Index: 1.465
• CAS DataBase Reference: 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one(57378-68-4)
• EPA Substance Registry System: 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one(57378-68-4)

Safety Data

• Hazardous Substances Data: 57378-68-4(Hazardous Substances Data)

Usage

Chemical Properties

Delta Damascone is a colorless to slightly yellow liquid with a very diffusive, fruity blackcurrant odor. Thematerial is prepared by Diels–Alder reaction of 1,3-pentadiene andmesityl oxide and subsequent aldol condensation of the resulting acetyl trimethyl cyclohexene with acetaldehyde. Due to its excellent substantive properties, ??- damascone is mainly used in perfumes for fabric care products.

Trade name

Delta Damascone

InChI:InChI=1/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8,10,12H,9H2,1-4H3

Upstream product

• 1093401-75-2 ethyl N,S-bis(4-oxo-4-(2’,6’,6’-trimethylcyclohex-3’-en-1’-yl)butan-2-yl)-L-cysteinate 

Downstream Products

• 1093401-75-2 ethyl N,S-bis(4-oxo-4-(2’,6’,6’-trimethylcyclohex-3’-en-1’-yl)butan-2-yl)-L-cysteinate 
• 1093401-74-1 methyl 2-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylamino)-3-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylthio)propanoate 
• 303185-64-0 C₂₂H₃₃NO₂ 

Relevant articles and documents

Cassis and Green Tea: Spontaneous Release of Natural Aroma Compounds from β-Alkylthioalkanones

In depth headspace analysis of the slow degradation of β-alkylthioalkanones in ambient air led to the discovery of a novel δ-cleavage pathway, by which β-mercaptoketones are released. Since β-mercaptoketones are potent natural aroma compounds occurring in many fruits, herbs and flowers, the discovery of an enzyme-independent molecular precursor for this class of high-impact molecules is of practical importance. Moreover, the formation of β-diketones and aldehydes by concomitant oxidation at the α-sulfur-position enhances the versatility of this class of aroma precursors. A mechanistic model is proposed which suggests that the oxidative degradation occurs through a novel Pummerer-type rearrangement of initially formed persulfoxides.

Aromatic aldols and 1,5-diketones as optimized fragrance photocages

Aromatic aldols and 1,5-diketones with abstractable γ-hydrogen atoms are highly photoactive cage molecules for the release of fragrance carbonyl compounds (aldehydes and Michael ketones, respectively). Aldols 3a-d are easily accessible by Mukaiyama addition and are cleaved to form the substrates with high quantum yields under solar radiation. By tuning the properties of the chromophores, a series of δ-damascone cages 5 were developed that can be used for selective and fast (5a,e) or slow (5b,d) release of fragrances under air and solar irradiation. The intermediates of the Norrish II process were observed by laser transient absorption spectroscopy.

Ketone precursors for organoleptic compounds

The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.