4-(3-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

Base Information

• Chemical Name: 4-(3-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
• CAS No.: 14398-34-6
• Molecular Formula: C13H20O2
• Molecular Weight: 208.301
• DSSTox Substance ID: DTXSID20708556
• Wikidata: Q82642956,Q104403087
• Mol file: 14398-34-6.mol

Synonyms:4-(3-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one;4-(3-hydroxy-2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one;DTXSID20708556;LICNQDPDQQOXCU-UHFFFAOYSA-N;1-(2,6,6,-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-3-oxo-1-butene;4-(2,6,6-trimethyl-3-hydroxy-cyclohex-1-en-1-yl)-but-3-en-2-one

Chemical Property of 4-(3-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 208.146329876
• Heavy Atom Count: 15
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1O)(C)C)C=CC(=O)C

Technology Process of 4-(3-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

There total 17 articles about 4-(3-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)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: 95.0%

(E)-4-(1,3,3-Trimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-but-3-en-2-one (190059-33-7,809237-15-8) → 4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one (14398-34-6)

Guidance literature:

With potassium carbonate; In methanol; Heating;

DOI:10.1016/j.tet.2009.09.074

Reference yield: 83.0%

(E)-β-ionone (79-77-6,14901-07-6) → 4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one (14398-34-6)

Guidance literature:

With P₃₈₆S mutant; sol-gel immobilised P₄₅₀ BM-3 A₇₄E; NADPH; In phosphate buffer; dimethyl sulfoxide; for 2h; pH=7.5; Enzymatic reaction;

DOI:10.1002/adsc.200303021

Reference yield: 75.0%

(E)-β-ionone (79-77-6,14901-07-6) → (rac)-(E)-4-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (116296-75-4) + 4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one (14398-34-6)

Guidance literature:

With Novosphingobium aromaticivorans DSM₁₂₄₄₄ [2Fe-2S] ferredoxin; Novosphingobium aromaticivorans DSM₁₂₄₄₄ cytochrome P₄₅₀ 101C₁; Novosphingobium aromaticivorans DSM₁₂₄₄₄ oxygenase-coupled NADH-dependent ferredoxin reductase; oxygen; NADH; bovine liver catalase; In ethanol; 2-amino-2-hydroxymethyl-1,3-propanediol; at 30 ℃; pH=7.4; Kinetics; Enzymatic reaction;

DOI:10.1002/cbic.201000537

upstream raw materials:

(E)-β-ionone

2,4,4-trimethyl-3-(3-oxobut-1-enyl)cyclohex-2-enyl acetate

(E)-4-(1,3,3-Trimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-but-3-en-2-one

alpha-ionone

Downstream raw materials:

3-oxo-butyric acid 2,4,4-trimethyl-3-((E)-3-oxo-but-1-enyl)-cyclohex-2-enyl ester

(R)-2-Phenyl-propionic acid (R)-2,4,4-trimethyl-3-((E)-3-oxo-but-1-enyl)-cyclohex-2-enyl ester

(R)-2-Phenyl-propionic acid (S)-2,4,4-trimethyl-3-((E)-3-oxo-but-1-enyl)-cyclohex-2-enyl ester

1-(2,6,6-Trimethyl-3-hydroxy-1-cyclohexene-1-yl)-3-methyl-penta-1,4-dien-3-ol