(E)-beta-Damascone

Base Information

• Chemical Name: (E)-beta-Damascone
• CAS No.: 23726-91-2
• Molecular Formula: C13H20O
• Molecular Weight: 192.301
• Hs Code.: 29142990
• European Community (EC) Number: 245-842-1
• UNII: I75J0X33Q6
• DSSTox Substance ID: DTXSID7051890
• Nikkaji Number: J422.324A,J57.950E
• Wikipedia: Damascone
• Wikidata: Q1051071
• Metabolomics Workbench ID: 45589
• ChEMBL ID: CHEMBL4565078
• Mol file: 23726-91-2.mol

Synonyms:alpha-damascone;damascone

Chemical Property of (E)-beta-Damascone

Chemical Property:

• Appearance/Colour: pale yellow clear liquid
• Vapor Pressure: 0.00655mmHg at 25°C
• Refractive Index: n20/D 1.498
• Boiling Point: 271.2 °C at 760 mmHg
• Flash Point: 108 °C
• PSA: 17.07000
• Density: 0.907 g/cm³
• LogP: 3.65820
• Storage Temp.: 2-8°C
• Water Solubility.: 192.3mg/L(25 oC)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 292

Purity/Quality:

99.9% ^*data from raw suppliers

β-Damascone technical, ≥90% (GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)C1=C(CCCC1(C)C)C
• Isomeric SMILES: C/C=C/C(=O)C1=C(CCCC1(C)C)C

Technology Process of (E)-beta-Damascone

There total 34 articles about (E)-beta-Damascone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

(E)-2,6,6-Trimethyl-α-(1-propenyl)-1-cyclohexene-1-methanol (35122-36-2) → beta damascone (23726-91-2)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1021/jo00290a057

Reference yield: 60.0%

(Z)-3-chloro-1-(2,6,6-trimethylcyclohex-1-enyl)but-2-en-1-one (77250-09-0) → beta damascone (23726-91-2)

Guidance literature:

With silver-zinc couple according to Heathcock;

DOI:10.1016/S0040-4039(00)92865-X

Reference yield:

4-(2',6',6'-trimethyl-1'-cyclohexenyl)-1,6-heptadien-4-ol (49815-59-0) → beta damascone (23726-91-2) + (Z)-1-(2',6',6'-trimethyl-1'-cyclohexenyl)-3-buten-1-one (23726-92-3) + 1-(2',6',6'-trimethyl-1'-cyclohexenyl)-3-buten-1-one (31089-73-3)

Guidance literature:

With potassium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 25 ℃; Yield given. Yields of byproduct given;

DOI:10.1002/hlca.19870700721

upstream raw materials:

β-ionone isoxazole

Damascenon

6,6-dimethyl-2-methyl-1-cyclohexene-1-carboxylic acid methyl ester

allylmagnesium bromide

Downstream raw materials:

3-hydroxymegastigma-5,8-dien-7-one

(E)-3-(but-2-enoyl)-2,4,4-trimethylcyclohex-2-enone

(S)-(+)-4-hydroxy-β-damascone

dihydro-β-damascol

Refernces

• 1、 Cavaleiro, José A. S.,Monteiro, Carlos J. P.,Moura, Nuno M. M.,P. M. S. Neves, M. Gra?a,Tomé, Augusto C.. "Synthesis of chlorins and bacteriochlorins from cycloaddition reactions with porphyrins". . . Retrieved 2022/02/10.
• 2、 Sarandeses, Luis A.,Luche, Jean-Louis. "A New Synthesis of α- and β-Damascones from the Ionones". . p. 2757 - 2760. Retrieved 2007/10/02.