beta-Ionone

Base Information

• Chemical Name: beta-Ionone
• CAS No.: 79-77-6
• Deprecated CAS: 1353674-22-2
• Molecular Formula: C13H20O
• Molecular Weight: 192.301
• Hs Code.: 2914 23 00
• European Community (EC) Number: 201-224-3,238-969-9
• NSC Number: 402758,46137
• UNII: A7NRR1HLH6
• DSSTox Substance ID: DTXSID4021769
• Nikkaji Number: J4.392C,J70.102E
• Wikidata: Q27114873
• RXCUI: 2371702
• Metabolomics Workbench ID: 47389
• ChEMBL ID: CHEMBL559945
• Mol file: 79-77-6.mol

Synonyms:4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one;beta-ionone;beta-ionone, (trans)-isomer

Chemical Property of beta-Ionone

Chemical Property:

• Vapor Pressure: <1 hPa (25 °C)
• Melting Point: -49 °C
• Refractive Index: n20/D 1.52(lit.)
• Boiling Point: 254.816 °C at 760 mmHg
• Flash Point: 121.291 °C
• PSA: 17.07000
• Density: 0.944 g/cm³
• LogP: 3.65820
• Storage Temp.: 2-8°C
• Solubility.: 0.11g/l insoluble
• Water Solubility.: Soluble in water (0.11 mg/mI at 20°C).
• 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
• Safety Statements: 61-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=O)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=O)C
• Uses: An aroma compound commonly found in essential oils such as rose oil. β-Lonone is an important fragrance chemical used in perfumery. β-Ionone is effective in the chemoprevention of rat mammary carcinogenesis. It is an important fragrance chemical used in perfumery. The combination of α-ionone and β-ionone is characteristic of the scent of violets and used with other components in flavoring to recreate their scent.

Technology Process of beta-Ionone

There total 144 articles about beta-Ionone 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:

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

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

2,2-dimethylglutaric acid

2,2-dimethyladipic acid

Refernces

Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles

10.1016/j.bmcl.2012.10.110

The research aimed to synthesize and evaluate novel terpenyl heterocycles based on chalcones and their dihydropyrazolidines/pyrazolidines for their potential as antileishmanial agents against Leishmania donovani, a parasite causing leishmaniasis. The study identified compound 4d as a promising candidate with significant in vitro activity against intracellular amastigotes of L. donovani, exhibiting an IC50 value of 7.49 μM and a selectivity index (S.I.) of 29.46, which was more active than the reference drug miltefosine. Compound 4d also showed a significant in vivo response in a hamster model with 81% inhibition of parasite multiplication. The chemicals used in the synthesis process included substituted aromatic aldehydes, b-ionone, and a-ionone for the chalcones, phenyl hydrazine for the formation of dihydropyrazolidine derivatives, and Ag2O for the aromatization of certain compounds. The study concluded that these terpenyl heterocycles could serve as prototypes for the development of more efficacious antileishmanial agents.

Synthesis of C15,C14′-ring locked all-trans-β-carotene

10.1016/S0040-4039(02)00663-9

The study presents the synthesis of a C15,C14-ring locked all-trans-β-carotene analog, which is a significant compound due to its role in the production of retinoids, essential for vision and cell differentiation. The synthesis involved the use of various chemicals, including cyclohexenone-3-carboxaldehyde, diethyl(1-cyanoethyl)phosphonate, and β-ionone, which served as starting materials and reagents in the reaction sequences. Key reactions such as Wittig and HWE olefinations were employed to construct the carbon framework, with the final product being synthesized through bis-olefination with a C15 ylide bearing the ionone moiety. This unnatural β-carotene analog preserves molecular connectivity upon oxidative cleavage, which is crucial for isotopic labeling studies to determine the source of oxygen in retinal production. The synthesized compound will be used for enzymatic oxidation studies, furthering understanding of β-carotene-15,15'-dioxygenase (BCDOX), an enzyme vital for retinoid production.