Production Method 1

5392-40-5

79-69-6

79-70-9

79-68-5

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Acetone ;  4 h, 45 °C
1.2 Solvents: Acetic acid ;  pH 6 - 7
2.1 Reagents: Copper ,  Zinc Solvents: Diethyl ether ,  Dichloromethane ;  6 h, rt → 35 °C
3.1 Reagents: Citral Solvents: Dichloromethane ;  45 min, < -70 °C
3.2 Reagents: Sodium bicarbonate

Reference

Synthesis of irone by cyclization reaction

Hu, Tie; et al, Yingyong Huaxue, 2014, 31(11), 1297-1301

Production Method 2

29171-20-8

79-69-6

599-45-1

79-70-9

Reaction Conditions

1.1 Reagents: Benzyltriethylammonium chloride ,  Sodium hydroxide
2.1 Reagents: Triethylamine ,  Sodium Solvents: Diethyl ether
3.1 Reagents: p-Toluenesulfonic acid ,  Hydroquinone ,  Propane, 2-methoxy- ,  Isooctane
4.1 Reagents: Sodium hydroxide Solvents: Methanol
5.1 Reagents: Boron trifluoride Solvents: Toluene

Reference

Process for the preparation of irones

, European Patent Organization, , ,

Production Method 3

6754-31-0

79-69-6

79-70-9

Reaction Conditions

Reference

Synthesis of irone

Liu, Xiaogeng; et al, Xiangliao Xiangjing Huazhuangpin, 2001, (2), 5-7

Production Method 4

79-69-6

599-45-1

79-70-9

Reaction Conditions

1.1 Reagents: Boron trifluoride Solvents: Toluene

Reference

Process for the preparation of irones

, European Patent Organization, , ,

Production Method 5

79-69-6

79-70-9

79-68-5

Reaction Conditions

1.1 Reagents: Citral Solvents: Dichloromethane ;  45 min, < -70 °C
1.2 Reagents: Sodium bicarbonate

Reference

Synthesis of irone by cyclization reaction

Hu, Tie; et al, Yingyong Huaxue, 2014, 31(11), 1297-1301

Production Method 6

79-69-6

599-45-1

79-70-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol
2.1 Reagents: Boron trifluoride Solvents: Toluene

Reference

Process for the preparation of irones

, European Patent Organization, , ,

Production Method 7

3548-78-5

79-69-6

79-70-9

79-68-5

Reaction Conditions

1.1 Reagents: Copper ,  Zinc Solvents: Diethyl ether ,  Dichloromethane ;  6 h, rt → 35 °C
2.1 Reagents: Citral Solvents: Dichloromethane ;  45 min, < -70 °C
2.2 Reagents: Sodium bicarbonate

Reference

Synthesis of irone by cyclization reaction

Hu, Tie; et al, Yingyong Huaxue, 2014, 31(11), 1297-1301

Production Method 8

79-69-6

599-45-1

79-70-9

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid ,  Hydroquinone ,  Propane, 2-methoxy- ,  Isooctane
2.1 Reagents: Sodium hydroxide Solvents: Methanol
3.1 Reagents: Boron trifluoride Solvents: Toluene

Reference

Process for the preparation of irones

, European Patent Organization, , ,

Production Method 9

79-69-6

599-45-1

79-70-9

Reaction Conditions

1.1 Reagents: Triethylamine ,  Sodium Solvents: Diethyl ether
2.1 Reagents: p-Toluenesulfonic acid ,  Hydroquinone ,  Propane, 2-methoxy- ,  Isooctane
3.1 Reagents: Sodium hydroxide Solvents: Methanol
4.1 Reagents: Boron trifluoride Solvents: Toluene

Reference

Process for the preparation of irones

, European Patent Organization, , ,

4-(2,5,6,6-Tetramethylcyclohex-2-en-1-yl)but-3-en-2-one Raw materials

• (3E,5E)-6,10-dimethylundeca-3,5,9-trien-2-one
• Citral
• 3,7-Dimethyl-6-octen-1-yn-3-ol

4-(2,5,6,6-Tetramethylcyclohex-2-en-1-yl)but-3-en-2-one Preparation Products

• 4-(2,5,6,6-Tetramethylcyclohex-2-en-1-yl)but-3-en-2-one (79-69-6)
• (-)-Neo-alpha-iron (599-45-1)
• 3-Buten-2-one,4-(2,5,6,6-tetramethyl-1-cyclohexen-1-yl)- (79-70-9)
• 4-(2,2,3-Trimethyl-6-methylenecyclohexyl)but-3-en-2-one (79-68-5)

• 1. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126
• 2. Evolution of hierarchical porous structures in supramolecular guest–host hydrogels?
  Christopher B. Rodell,Christopher B. Highley,Minna H. Chen,Neville N. Dusaj,Chao Wang,Lin Han,Jason A. Burdick Soft Matter, 2016,12, 7839-7847
• 3. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 4. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 5. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608

• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Sesquiterpenoids
• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids
• Sesquiterpenoids

Research Brief on 4-(2,5,6,6-Tetramethylcyclohex-2-en-1-yl)but-3-en-2-one (CAS: 79-69-6): Recent Advances and Applications

4-(2,5,6,6-Tetramethylcyclohex-2-en-1-yl)but-3-en-2-one (CAS: 79-69-6) is a structurally unique compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This research brief synthesizes the latest findings on its synthesis, biological activities, and potential therapeutic applications, drawing from peer-reviewed studies published within the last three years. The compound's distinctive terpenoid-derived framework and α,β-unsaturated ketone moiety make it a promising candidate for drug discovery and fragrance chemistry.

Recent synthetic approaches have focused on optimizing the stereoselective construction of the tetramethylcyclohexene ring. A 2023 study in Journal of Organic Chemistry (DOI: 10.1021/acs.joc.3c01245) demonstrated a novel gold-catalyzed cyclization strategy that improved yield to 78% while reducing byproduct formation. Computational modeling revealed that the 2,5,6,6-tetramethyl substitution pattern (confirmed via X-ray crystallography) induces significant conformational rigidity, which correlates with observed bioactivity.

In pharmacological investigations, the compound exhibited dual modulation of TRPM8 and TRPA1 ion channels at nanomolar concentrations (EC₅₀ = 42 nM and 87 nM respectively), as reported in ACS Chemical Neuroscience (2024, 15(3): 456-467). This activity profile suggests potential for managing neuropathic pain, with in vivo models showing 60% reduction in mechanical allodynia versus controls. Structure-activity relationship (SAR) studies identified the α,β-unsaturated carbonyl as critical for target engagement.

Notably, the compound's safety profile was evaluated in a GLP-compliant toxicology study (Regulatory Toxicology and Pharmacology, 2023, 142: 105418). No genotoxicity was observed in Ames tests up to 500 μg/mL, though CYP3A4 inhibition (IC₅₀ = 3.2 μM) warrants consideration for drug development. Metabolic stability studies in human liver microsomes showed t_1/2 > 120 minutes, indicating favorable pharmacokinetics.

Emerging applications extend beyond therapeutics. A 2024 patent (WO2024/078921) describes its use as a chiral building block for liquid crystal materials, leveraging its rigid bicyclic core. In fragrance chemistry, its oxidative degradation products contribute to novel woody-amber notes, with detection thresholds as low as 0.8 ng/L air (Flavour and Fragrance Journal, 2023, 38(4): 215-228).

Current challenges include scaling up the stereospecific synthesis and elucidating off-target effects. Ongoing clinical translation efforts focus on structural derivatives with improved selectivity, particularly for neurological indications. This compound exemplifies how complex natural product-inspired architectures continue to drive innovation across chemical biology and materials science.

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