79-89-0

Basic information

• Product Name: 3-BUTEN-2-ONE, 3-METHYL-4-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)
• Synonyms: METHYL IONONE DELTA;DELTA-METHYLIONONE;3-BUTEN-2-ONE, 3-METHYL-4-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL);3-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-on;3-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-Buten-2-one;4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-methyl-3-buten-2-one;4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-methyl-3-buten-2-one;iso-Methyl-beta-ionone
• CAS NO: 79-89-0
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.32
• EINECS: 201-231-1
• Mol File: 79-89-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 301.3°C at 760 mmHg
• Flash Point: 130.9°C
• Appearance: /
• Density: 0.937g/cm³
• Vapor Pressure: 0.00106mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: 3-BUTEN-2-ONE, 3-METHYL-4-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BUTEN-2-ONE, 3-METHYL-4-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)(79-89-0)
• EPA Substance Registry System: 3-BUTEN-2-ONE, 3-METHYL-4-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)(79-89-0)

Safety Data

• Hazardous Substances Data: 79-89-0(Hazardous Substances Data)

Usage

Uses

Isomethyl-β-ionone was identified in the composition of mackerel head broth and mackerel bone broth. A volatile flavour compound.

InChI:InChI=1/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h9H,6-8H2,1-5H3/b11-9+

Upstream product

• 26651-96-7 7,11-dimethyl-dodeca-4,6,10-trien-3-one 
• 1551070-65-5 2-methyl-3-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)-tri-2-monoenenitrile 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 

Downstream Products

• 661492-86-0 (2E,4E)-3,4-dimethyl-5-(2’,6’,6’-trimethylcyclohex-1’-en-1’-yl)penta-2,4-dienal 

Relevant articles and documents

Synthetic control of retinal photochemistry and photophysics in solution

Understanding how molecular structure and environment control energy flow in molecules is a requirement for the efficient design of tailor-made photochemistry. Here, we investigate the tunability of the photochemical and photophysical properties of the retinal-protonated Schiff base chromophore in solution. Replacing the n-butylamine Schiff base normally chosen to mimic the saturated linkage found in nature by aromatic amines results in the reproduction of the opsin shift and complete suppression of all isomerization channels. Modification of retinal by directed addition or removal of backbone substituents tunes the overall photoisomerization yield from 0 to 0.55 and the excited state lifetime from 0.4 to 7 ps and activates previously inaccessible reaction channels to form 7-cis and 13-cis products. We observed a clear correlation between the presence of polarizable backbone substituents and photochemical reactivity. Structural changes that increase reaction speed were found to decrease quantum yields, and vice versa, so that excited state lifetime and efficiency are inversely correlated in contrast to the trends observed when comparing retinal photochemistry in protein and solution environments. Our results suggest a simple model where backbone modifications and Schiff base substituents control barrier heights on the excited-state potential energy surface and therefore determine speed, product distribution, and overall yield of the photochemical process.