alpha-IONONE

Base Information

• Chemical Name: alpha-IONONE
• CAS No.: 127-41-3
• Deprecated CAS: 30685-95-1,31798-11-5,31798-11-5
• Molecular Formula: C13H20O
• Molecular Weight: 192.301
• Hs Code.: 29142300
• European Community (EC) Number: 204-841-6
• UNII: I9V075M61R
• ChEMBL ID: CHEMBL472877
• DSSTox Substance ID: DTXSID0035160
• Metabolomics Workbench ID: 54536
• Nikkaji Number: J183.660I,J2.016H,J278.189A
• NSC Number: 34560
• RXCUI: 1859172
• Wikidata: Q27114869
• Mol file: 127-41-3.mol

Synonyms:alpha-ionone;alpha-ionone, (+)-iosmer;alpha-ionone, (E)-(+-)-isomer;alpha-ionone, (E)-isomer

Chemical Property of alpha-IONONE

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 0.0144mmHg at 25°C
• Melting Point: 59 - 61oC
• Refractive Index: n20/D 1.498(lit.)
• Boiling Point: 257.604 °C at 760 mmHg
• Flash Point: 111.901 °C
• PSA: 17.07000
• Density: 0.935 g/cm³
• LogP: 3.51410
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ethanol fixed oils, propylene glycol. Slightly solubl
• Water Solubility.: insoluble
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 282

Purity/Quality:

99% ^*data from raw suppliers

alpha-Ionone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 42-36-36/37/38
• Safety Statements: 36-24/25-26-36/37/39-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CCCC(C1C=CC(=O)C)(C)C
• Isomeric SMILES: CC1=CCCC(C1/C=C/C(=O)C)(C)C
• Description: The alpha-ionone is the alpha form of ionone. The ionones denote a series of chemical substances belonging to rose ketones including carotene, damascenes and damascenones. It is found in various kinds of essential oils contained in some flowers such as violet. Ionone has three forms including alpha-, beta and gamma-. The alpha-ionone has the aroma odor of violet, which has been widely used in daily chemical flavor and tobacco-used flavor. The alpha-ionone can be made from the thermal decomposition of carotene. α-Ionone has a characteristic violet-like odor. α-Ionone may be prepared by condensing citral with acetone to form pseudoionone, which is then cyclized by acid-type reagents.
• Uses: An aroma compound commonly found in essential oils such as rose oil. It is a degradation products of caratenoids produced by caratenoid cleavage dioxygenases (CCD). alpha-Ionone, is used in many floral accords. Gives a violet flower nuance to compositions, but is also used in rose, woody, amber, balsamic, and powdery fragrances. It is also used in perfumery, flavoring, and vitamin A (retinol) production for cosmetics and toiletries. beta isomer shows a less floral odor than the alpha. It has good substantivity and is used in all areas of perfumery.

Technology Process of alpha-IONONE

There total 82 articles about alpha-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: 96.0%

α-cyclocitral (14505-74-9,41721-03-3,59462-59-8,432-24-6) + diethyl [2-(butylimino)propyl]phosphonate anion → 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 lithium diisopropyl amide; In tetrahydrofuran; hexane; toluene; at -80 - 20 ℃; for 2h;

DOI:10.1002/ejoc.200400201

Reference yield: 95.0%

alpha-ionol (25312-34-9) → 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 sodium hydroxide; dipotassium peroxodisulfate; nickel(II) sulphate; In dichloromethane; water; for 24h; Ambient temperature;

upstream raw materials:

formic acid

pseudoionone

acetic acid

α-cyclocitral

Downstream raw materials:

4,4-dimethyl-6-oxo-heptanoic acid

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

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

4-(2,2,6-trimethylcyclohexyl)-butan-2-one

Refernces

• 1、 Royals. "-". . p. 546. Retrieved 1946.
• 2、 Lin, Zhenghuan,Zhao, Chengxue. "Macroreticular p-(ω-sulfonic-perfluoroalkylated) polystyrene ion-exchange resins: A new type of selective solid acid catalyst". . p. 3556 - 3558. Retrieved 2005.
• 3、 Rachwalik,Michorczyk,Ogonowski. "Cyclization of pseudoionone into α-Ionone over heteropolyacid supported on mesoporous silica SBA-15". . p. 1384 - 1390. Retrieved 2011.
• 4、 Lin, Zhenghuan,Huang, Limei,Ling, Qidan,Chen, Hong,Zhao, Chengxue. "ω-Sulfonic-perfluoroalkylated poly(styrene-maleic anhydride)/silica hybridized nanocomposite as a new kind of solid acid catalyst". . p. 73 - 79. Retrieved 2012.
• 5、 Díez,Apesteguía,Di Cosimo. "Synthesis of ionones on solid Br?nsted acid catalysts: Effect of acid site strength on ionone isomer selectivity". . p. 267 - 274. Retrieved 2010.
• 6、 -. "Continuous preparation method of high-selectivity alpha-ionone". Paragraph 0033-0071. . Retrieved 2020/08/06.
• 7、 Paret, Nicolas,Trachsel, Alain,Berthier, Damien L.,Herrmann, Andreas. "Controlled release of encapsulated bioactive volatiles by rupture of the capsule wall through the light-induced generation of a gas". supporting information. p. 2275 - 2279. Retrieved 2015/02/19.