23726-91-2

Basic information

• Product Name: DAMASCONE
• Synonyms: (E)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one;(e)-1-(2,6,6-trimethylcyclohex-1-enyl)-2-buten-1-one;(e)-beta-damascone;1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-,(E)-2-Buten-1-one;6,6-trimethyl-1-cyclohexen-1-yl)-1-((e)-2-buten-1-on;6,6-trimethylcyclohex-1-enyl)-1-((e)-2-buten-1-on;rosedihydroketone;trans-.beta.-Damascone
• CAS NO: 23726-91-2
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.3
• EINECS: 245-842-1
• Mol File: 23726-91-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 271℃
• Flash Point: 108℃
• Appearance: /
• Density: 0.934 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00655mmHg at 25°C
• Refractive Index: n20/D 1.498
• Storage Temp.: 2-8°C
• Water Solubility: 192.3mg/L(25 oC)
• BRN: 2046078
• CAS DataBase Reference: DAMASCONE(CAS DataBase Reference)
• NIST Chemistry Reference: DAMASCONE(23726-91-2)
• EPA Substance Registry System: DAMASCONE(23726-91-2)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 2
• RTECS: EN0340000
• F: 10-23
• Hazardous Substances Data: 23726-91-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 9128, 1972 DOI: 10.1021/ja00781a023

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7H,6,8-9H2,1-4H3/b7-5+

Upstream product

• 49815-59-0 4-(2',6',6'-trimethyl-1'-cyclohexenyl)-1,6-heptadien-4-ol 
• 1197-92-8 1-(2,6,6-trimethyl-cyclohex-1-enyl)-ethanone 
• 41613-59-6 1-ethynyl-2,2,6-trimethyl-1-cyclohexanol 
• 2816-57-1 2,6-dimethylcyclohexanone 
• 20013-73-4 2,6,6-trimethylcyclohex-2-en-1-one 
• 41641-09-2 1-(3-hydroxy-but-1-ynyl)-2,2,6-trimethyl-cyclohexanol 
• 43126-16-5 4-(2,2,6-Trimethylcyclohex-1-en-1-yl)-3-butin-2-yl-acetat 
• 35044-57-6 ethyl 2,6,6-trimethyl-2,4-cyclohexadiene-1-carboxylate 
• 35044-59-8 2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxylic acid ethyl ester 
• 35044-62-3 1-(2,6,6-Trimethyl-cyclohexa-2,4-dienyl)-but-3-en-1-one 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 127724-39-4 (E)-1-(2,6,6-trimethylcyclohex-1-en-1-yl)-3-(trimethylsilyl)but-1-ene 
• 53319-91-8 (E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-yl acetate 
• 22029-76-1 beta-ionol 

Downstream Products

• 35734-61-3 3-hydroxymegastigma-5,8-dien-7-one 
• 119207-19-1 (E)-3-(but-2-enoyl)-2,4,4-trimethylcyclohex-2-enone 
• 1447716-75-7 (S)-(+)-4-hydroxy-β-damascone 
• 42742-79-0 dihydro-β-damascol 
• 28384-26-1 1-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-1-one 
• 1268363-53-6 3,4-epoxy-β-damascone 
• 1268363-54-7 3-hydroxy-4-oxo-β-damascone 
• 125316-28-1 3-<3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-oxo-1-methyl-1-propyl>-5-<(E)-3-(acetyloxy)-1-methyl-1-propenyl>-isoxazole 
• 125316-31-6 3-<3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hydroxy-1-methyl-1-propyl>-5-<(E)-3-(acetyloxy)-1-methyl-1-propenyl>-isoxazole 
• 125316-32-7 3-<(E)-3-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-1-methyl-1-propyl>-5-<(E)-3-(acetyloxy)-1-methyl-1-propenyl>-isoxazole 
• 125316-29-2 3-<3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-oxo-1-methyl-1-propyl>-5-<(E)-3-hydroxy-1-methyl-1-propenyl>-isoxazole 
• 125316-30-5 3-<3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hydroxy-1-methyl-1-propyl>-5-<(E)-3-hydroxy-1-methyl-1-propenyl>-isoxazole 
• 23726-92-3 (Z)-1-(2',6',6'-trimethyl-1'-cyclohexenyl)-3-buten-1-one 

Relevant articles and documents

Synthesis of (E)-1-Propenyl Ketones from Carboxylic Esters and Carboxamides by Use of Mixed Organolithium-Magnesium Reagents

The novel reagents formed by combination of allylmagnesium chloride and a strong non-nucleophilic lithium base (LiNR2) convert non- or slowly enolizable carboxylic esters or carboxamides into 2-propenyl ketones which are protected from further reaction by their in situ conversion into enolates.This modified Grignard reaction is applied to efficient syntheses of α-damascone, β-damascone, β-damascenone, and various other (E)-1-propenyl ketones.

Synthesis method of beta-damascenone

The invention provides a synthesis method of beta-damascenone. The synthesis method comprises the following steps: 1) carrying out nucleophilic addition reaction on a compound II and acetylene to generate a compound III; (2) carrying out condensation reaction on the compound III and acetaldehyde to generate a compound IV, and (3) carrying out Meyer-Schureter rearrangement reaction on the compoundIV to obtain a compound V, namely the beta-damascenone.

Transformation of α- and β-Ionones into α- and β-Damascone and β-Damascenone Using Allylsilane Chemistry

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