23726-92-3

Basic information

• Product Name: (Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one
• Synonyms: BETA-DAMASCONE;DAMASCONE (BETA);DAMASCONE;FEMA 3243;1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-,(Z)-2-Buten-1-one;1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-cis-2-Buten-1-one;2-Buten-1-one,1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-,(Z)-;6,6-trimethyl-1-cyclohexen-1-yl)-1-((z)-2-buten-1-on
• CAS NO: 23726-92-3
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.3
• EINECS: 245-842-1
• Mol File: 23726-92-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 271.2 ºC at 760 mmHg
• Flash Point: 108 ºC
• 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(temperature not stated)
• CAS DataBase Reference: (Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one(23726-92-3)
• EPA Substance Registry System: (Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one(23726-92-3)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 2
• RTECS: EN0340000
• F: 10-23
• Hazardous Substances Data: 23726-92-3(Hazardous Substances Data)

Usage

Description

(Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, also known as (Z)-beta-damascone, is a colorless to pale yellow liquid with floral, fruity, and rose-like aromas. It is a naturally occurring compound found in various fruits and is widely used in the fragrance and flavor industries due to its pleasant scent.

Uses

Used in the Food Industry:
(Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one is used as a food spice for formulating rose essence, adding a distinct and pleasant aroma to various food products.
Used in the Fragrance Industry:
(Z)-beta-damascone is used as a key ingredient in the creation of perfumes and other fragrances, providing a natural and captivating rose-like scent.
Used in the Flavor Industry:
(Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one is also utilized in the flavor industry to enhance the taste and aroma of various products, such as beverages, confectionery, and other consumables, by imparting a fruity and floral note.

Synthesis

(Z)-beta-damascone can be synthesized by the reaction of ethyl crocinate and allyl lithium, followed by catalytic isomerization.

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

• 49815-58-9 6,6-dimethyl-2-methyl-1-cyclohexene-1-carboxylic acid methyl ester 
• 2622-05-1 allylmagnesium bromide 
• 35124-05-1 2,6,6-Trimethyl-α-(1-propenyl)-1-cyclohexene-1-methanol 
• 49815-59-0 4-(2',6',6'-trimethyl-1'-cyclohexenyl)-1,6-heptadien-4-ol 
• 23726-91-2 beta damascone 
• 67-63-0 isopropyl alcohol 
• 79-77-6 (E)-β-ionone 
• 139609-04-4 2-(1-Bromoethyl)-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)oxirane 
• 139609-02-2 α-Methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)oxiranemethanol 
• 139609-00-0 1-<3-(2,6,6-Trimethyl-1-cyclohexen-1-yl)oxiranyl>ethanone 

Relevant articles and documents

A New Synthesis of α- and β-Damascones from the Ionones

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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.