beta-Methylionone

Base Information

• Chemical Name: beta-Methylionone
• CAS No.: 63429-28-7
• Deprecated CAS: 1335-68-8,8053-28-9
• Molecular Formula: C14H22 O
• Molecular Weight: 206.328
• European Community (EC) Number: 264-140-6,204-843-7,215-341-2
• NSC Number: 163995
• UNII: 54PXU8D4R5
• DSSTox Substance ID: DTXSID401036355
• Nikkaji Number: J151.171H,J208.706E
• Wikidata: Q27160975
• Metabolomics Workbench ID: 48062
• Mol file: 63429-28-7.mol

Synonyms:beta-Methylionone;beta methyl ionone;127-43-5;beta-Iraldeine;beta-Methyl ionone;Methyl-beta-ionone;.beta.-Methylionone;Methyl-.beta.-ionone;.beta.-Ionone, methyl-;.beta.-Iraldeine;Cetone, beta-;63429-28-7;1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one;FEMA No. 2712;beta-Ionone, methyl-;1-PENTEN-3-ONE, 1-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-;UNII-54PXU8D4R5;5-(2,6,6-Trimethyl-1-cyclohexenyl)-4-penten-3-one;54PXU8D4R5;(E)-1-(2,6,6-trimethylcyclohexen-1-yl)pent-1-en-3-one;(E)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)pent-1-en-3-one;EINECS 204-843-7;EINECS 215-341-2;EINECS 264-140-6;NSC 163995;NSC-163995;1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)pent-1-en-3-one;(1E)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one;AI3-24259;3-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, monomethyl deriv.;EC 264-140-6;1322-71-0;(1E)-1-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-1-en-3-one;4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one, monomethyl derivative;b-Methylionone;methyl beta-ionone;1-Methyl-b-ionone;beta-N-Methyl ionone;(E)-beta-methyl ionone;.BETA.-CETONE;.beta.-N-Methyl ionone;.BETA.-METHYL IONONE;SCHEMBL1404271;SCHEMBL1404273;CHEBI:88921;FEMA 2712;1-Penten-3-one,1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-;LMWNGLDCJDIIBR-CMDGGOBGSA-N;DTXSID401036355;METHYL-.BETA.-IONONE [FHFI];MFCD00031478;NSC163995;5-(2,6-Trimethyl-1-cyclohexenyl)-4-penten-3-one;1-Penten-3-one,6,6-trimethyl-1-cyclohexen-1-yl)-;1-penten-3-one-(2,6,6-trimethyl-1-cyclohen-1-yl);Q27160975;5-(2,6, 6-Trimethyl-1-cyclohexenyl)-4-penten-3-one;1(E)-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-1-en-3-one;1-(2 2 6-Trimethylcyclohex-1-en-1-yl)-1-penten-3-one;1-penten-3-ona, 1-(2,6,6-trimetil-1-ciclohexen-1-il)-;5-(2 6 6-Trimethyl-1-cyclohexen-1-yl)-4-penten-3-one;5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-penten-3-one;1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one #;1 - (2,6,6 - trimethyl - 1 - cyclohexen - 1 - yl)pent - 1 - en - 3 - one

Chemical Property of beta-Methylionone

Chemical Property:

• Vapor Pressure: 0.82Pa at 25℃
• Boiling Point: 281℃[at 101 325 Pa]
• PSA: 17.07000
• Density: 0.938[at 20℃]
• LogP: 4.04830
• Water Solubility.: 13.4mg/L at 20℃
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 206.167065321
• Heavy Atom Count: 15
• Complexity: 305

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)C=CC1=C(CCCC1(C)C)C
• Isomeric SMILES: CCC(=O)/C=C/C1=C(CCCC1(C)C)C

Technology Process of beta-Methylionone

There total 14 articles about beta-Methylionone 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: 83.0%

ethylmagnesium bromide (925-90-6) + (2E)-N-methoxy-N-methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenamide (141208-06-2) → (4E)-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-penten-3-one (63429-28-7)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1248/cpb.47.171

Reference yield:

butanone (78-93-3) → (4E)-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-penten-3-one (63429-28-7) + alpha-Methyl-ionone (93302-56-8,7779-30-8)

Guidance literature:

With sodium ethanolate; Destillieren der nach dem Ansaeuern mit wss. Essigsaeure erhaltenen Reaktionsprodukte unter vermindertem Druck;

Reference yield:

butanone (78-93-3) → (4E)-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-penten-3-one (63429-28-7) + alpha-Methyl-ionone (93302-56-8,7779-30-8)

Guidance literature:

With sodium ethanolate; Destillieren der nach dem Ansaeuern mit wss. Essigsaeure erhaltenen Reaktionsprodukte unter vermindertem Druck;

upstream raw materials:

(E)-β-ionone

methyl iodide

ethyl bromide

(E)-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenal S,S-acetal

Downstream raw materials:

1-(3-ethyl-5,6,7,8-tetrahydro-8,8-dimethyl-2-naphthalenyl)ethanone

6-ethyl-1,2,3,4-tetrahydro-1,1,6-trimethylnaphthalene

Refernces

• 1、 Wada, Akimori,Fujioka, Naoko,Ito, Masayoshi. "Retinoids and related compounds. Part 22. Synthesis of β-ionone analog tricarbonyliron complexes". . p. 171 - 176. Retrieved 2007/10/03.
• 2、 Groesbeek, M.,Steen, R. van der,Vliet, J. C. van,Vertegaal, L. B. J.,Lugtenburg, J.. "Synthesis of three retinal models, including the 10-s-cis-locked retinal, all-E-12,19-methanoretinal". . p. 427 - 436. Retrieved 2007/10/02.