4-(2,6,6-Trimethyl-cyclohex-1-enyl)-but-3-en-2-one

Base Information

• Chemical Name: 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-but-3-en-2-one
• CAS No.: 14901-07-6
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.301
• Hs Code.: 2914.23
• DSSTox Substance ID: DTXSID9025451
• Wikidata: Q27190018
• Metabolomics Workbench ID: 130624
• ChEMBL ID: CHEMBL3184146
• Mol file: 14901-07-6.mol

Synonyms:4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one;3-Buten-2-one, 4-(2,2,6-trimethylcyclohexenyl)-;4-(2,6,6-Trimethyl-cyclohex-1-enyl)-but-3-en-2-one;DTXSID9025451;b-lonone;CHEMBL3184146;AKOS028109879;FT-0622918;FT-0627280;FT-0670401;I0077;4-(2,6,6-trimethylcyclohexen-1-yl)-3-buten-2-one

Chemical Property of 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-but-3-en-2-one

Chemical Property:

• Appearance/Colour: clear slightly yellow to yellow liquid
• Vapor Pressure: 1.706Pa at 25℃
• Melting Point: -49 °C
• Refractive Index: 1.517 - 1.522
• Boiling Point: 254.8 °C at 760 mmHg
• PKA: 0[at 20 ℃]
• Flash Point: 121.3 °C
• PSA: 17.07000
• Density: 0.944 g/cm³
• LogP: 3.65820
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: 2.9
• 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% ^*data from raw suppliers

β-Ionone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, N
• Hazard Codes: Xi,N
• Statements: 38-51/53-36/37/38
• Safety Statements: 61-36/37/39-27-26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=O)C
• Description: β-Ionone has a characteristic violet-like odor, more fruity and woody than α-ionone. May be prepared by condensing citral with acetone to form pseudoionone, which is then cyclized by acid-type reagents.
• Uses: beta-Lonone is an essential oil extract from the leaves and flowers of Succisa Pratensis that shows antioxidant and antimicrobial activities against bacteria. β-Ionone may be used as a reference standard in the determination of β-ionone in wine using solid-phase extraction followed by gas chromatography with mass spectrometry (GC-MS).

Technology Process of 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-but-3-en-2-one

There total 149 articles about 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-but-3-en-2-one 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: 98.0%

5E-6,10-dimethylundeca-3,5,9-trien-2-one (62692-61-9,3548-78-5) → (E)-β-ionone (79-77-6,14901-07-6) + alpha-ionone (127-41-3,6901-97-9,14398-36-8,24190-29-2,30685-95-1,31798-12-6,52340-45-1,67529-94-6,67529-95-7)

Guidance literature:

With hydrogen fluoride; at 0 - 5 ℃; for 0.333333h;

DOI:10.1007/BF02465747

Reference yield: 88.2%

pseudoionone (141-10-6,3548-78-5) → (E)-β-ionone (79-77-6,14901-07-6) + alpha-ionone (127-41-3,6901-97-9,14398-36-8,24190-29-2,30685-95-1,31798-12-6,52340-45-1,67529-94-6,67529-95-7)

Guidance literature:

With sulfuric acid; water; In dichloromethane; at -20 - 5 ℃; for 0.916667h; Product distribution / selectivity;

Reference yield: 62.0%

β-carotene (161023-01-4) → 2,2,6-trimethylcyclohexan-1-one (2408-37-9) + (E)-β-ionone (79-77-6,14901-07-6) + 2,6,6-trimethylcyclohex-1-enecarbaldehyde (432-25-7)

Guidance literature:

With oxygen; In ethyl acetate; at 80 ℃; Catalytic behavior;

DOI:10.1016/j.cclet.2020.07.031

upstream raw materials:

pseudoionone

alpha-ionone

α-cyclocitral

acetone

Downstream raw materials:

(2E,4E,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid

(+/-)-3,7-dimethyl-1t-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,6ξ,8-trien-4-yn-3-ol

(+/-)-7-hydroxy-3,7-dimethyl-9t-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2t,8-dien-4-ynoic acid ethyl ester

4-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-one semicarbazone

Refernces

• 1、 Fleischmann, Peter,Watanabe, Naoharu,Winterhalter, Peter. "Enzymatic carotenoid cleavage in star fruit (Averrhoa carambola)". . p. 131 - 137. Retrieved 2003.
• 2、 Cais,Maoj. "". . p. 370,380, 381. Retrieved 1966.
• 3、 Wache, Yves,Bosser-DeRatuld, Aurelie,Lhuguenot, Jean-Claude,Belin, Jean-Marc. "Effect of cis/trans isomerism of β-carotene on the ratios of volatile compounds produced during oxidative degradation". . p. 1984 - 1987. Retrieved 2003.
• 4、 Gandomkar, Somayyeh,Rocha, Raquel,Sorgenfrei, Frieda A.,Montero, Lía Martínez,Fuchs, Michael,Kroutil, Wolfgang. "PQQ-dependent Dehydrogenase Enables One-pot Bi-enzymatic Enantio-convergent Biocatalytic Amination of Racemic sec-Allylic Alcohols". . p. 1290 - 1293. Retrieved 2020/12/23.
• 5、 Mosaferi, Shabnam,Jelley, Rebecca E.,Fedrizzi, Bruno,Barker, David. "Scalable synthesis of the aroma compounds d6-β-ionone and d6-β-cyclocitral for use as internal standards in stable isotope dilution assays". supporting information. . Retrieved 2020/12/02.