Citral

Base Information

• Chemical Name: Citral
• CAS No.: 5392-40-5
• Deprecated CAS: 1392408-16-0,250599-19-0,37350-34-8,433282-33-8,96680-15-8
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Hs Code.: 2912.19
• DSSTox Substance ID: DTXSID6024836
• Wikidata: Q60176530
• Metabolomics Workbench ID: 127890
• ChEMBL ID: CHEMBL2297541
• Mol file: 5392-40-5.mol

Synonyms:3,7-Dimethyl-2,6-octadien-1-al;3,7-Dimethyl-2,6-octadienal;Citral PQ Extra;Lemarome N;Lemsyn GB;NSC 6170;2,6-Octadienal,3,7-dimethyl-;

Chemical Property of Citral

Chemical Property:

• Appearance/Colour: yellow liquid
• Vapor Pressure: 0.2 mm Hg ( 200 °C)
• Melting Point: < -10oC
• Refractive Index: 1.484 - 1.490
• Boiling Point: 229 °C at 760 mmHg
• Flash Point: 101.7 °C
• PSA: 17.07000
• Density: 0.856 g/cm³
• LogP: 2.87800
• Storage Temp.: 2-8°C
• Solubility.: 0.42g/l
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

Citral ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38-43
• Safety Statements: 24/25-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCCC(=CC=O)C)C
• Production method: Citral natural exists in the litsea cubeba oil (about 80%), lemon grass oil (80%), clove basil oil (65%), sour lemon oil (35%) and lemon oil. In industry, citral can be derived from natural essential oils, or be prepared by chemical. Synthesis based on methyl heptenone as raw material Ethoxyacetylene magnesium bromide and methyl heptenone performed condensation reaction to form 3,7-dimethyl-1-ethoxy-3-hydroxy-6-octene-1-yne, which was then partly hydrogenated in the presence of catalysis to generate enol ether. And the enol ether was then hydrolyzed with phosphoric acid and dehydrated to obtain citral, with a yield of 68% calculated by methyl heptenone. In addition, acetylene and methyl heptenone could perform condensation reaction to form dehydrogenation linalool, which was then rearranged in the presence of silicon sulfone catalysis at 140~150 °C in inert solvent to get citral. Derived from litsea cubeba oil (which is the main method to product citral in China) Add 30 kg of cubeba oil containing about 75% of citral into a mixture under fully stirring, which was prepared with 18 kg of sodium bicarbonate, 38 kg of sodium sulfite and about 165 kg of water, and then continually stir for 5 to 6 h at room temperature. After standing overnight for stratification, the lower citral precipitated in the form of adduct. And the adduct was then washed with a small amount of toluene to remove oil and dried. And then add 10% sodium hydroxide solution to decompose citral at room temperature, and extract it with benzene. The extract was first distilled at atmospheric pressure (80-82°C) to recover benzene and then distilled under reduced pressure to collect fractions of 110-111°C (1.47kPa) to obtain pure product of 98% citral in an amount of about 15 to 16 kg.
• Uses: Citral is a liquid flavoring agent, light yellow in color with a citrus odor. it occurs in lemon and lemongrass oils. it is usually obtained from citral-containing oils by chemical means but may also be pre- pared synthetically. it is soluble in fixed oils, mineral oil, and pro- pylene glycol. it is moderately stable and should be stored in glass, tin, or resin-lined containers. it is used in flavors for lemon with applications in candy, baked goods, and ice cream at 20–40 ppm. it is also termed 2,6-dimethyl-octadian-2-6-al-8. Citral is an anti-microbial agent found in plants with antibacterial activity against some food pathogens. It is also a fragrance compound with a distinct lemon scent. citral is a naturally occurring aroma compound used to provide a lemon-type fragrance. Citral is a constituent of lemon oil, lemongrass oil, lime oil, ginger oil, verbena oil, and other plant-derived C essential oils.

Technology Process of Citral

There total 107 articles about Citral 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: 99.0%

geraniol (624-15-7) → (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8)

Guidance literature:

With triphenyl(2,6-dimethylphenyl)bismuthonium tetrafluoroborate; N,N,N',N'-tetramethylguanidine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1246/bcsj.81.1621

Reference yield: 98.0%

3,7-dimethylocta-2,6-dienal oxime (13372-77-5) → (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8)

Guidance literature:

With aluminum oxide; tripropylammonium fluorochromate (VI); In dichloromethane; for 0.5h;

DOI:10.1081/SCC-120001501

Reference yield: 98.0%

Nerol (106-25-2) → (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8)

Guidance literature:

With bis(pentafluorophenyl)borinic acid; magnesium sulfate; pivalaldehyde; In toluene; for 3h; Ambient temperature;

DOI:10.1021/jo970959d

upstream raw materials:

quinoline

meta-dinitrobenzene

Geraniol

sodium carbonate

Downstream raw materials:

4,8-dimethyl-1,3,7-nonatriene

1,1-diethoxy-3,7-dimethylocta-2,6-diene

1-(5-benzyl-[2]thienyl)-5,9-dimethyl-deca-2,4,8-trien-1-one

9,13-dimethyl-tetradeca-111,6,8,12-tetraen-5-one

Refernces

• 1、 Chrobok, Anna,Baj, Stefan,Pud?o, Wojciech,Jarz?bski, Andrzej. "Supported ionic liquid phase catalysis for aerobic oxidation of primary alcohols". . p. 179 - 185. Retrieved 2010.
• 2、 Alves, Otávio A. L.,Chagas, Rafael C. R.,Princival, Jefferson L.,Ribeiro, RogérioT.,Silva, Emmanuel D.,Villar, José A. F. P.. "Homogeneous CuCl2/TMEDA/TEMPO-Catalyzed chemoselective base- and halogen- free aerobic oxidation of primary alcohols in mild conditions". . . Retrieved 2021/08/03.
• 3、 da Silva, Marcio Jose,da Silva Andrade, Pedro Henrique,Sampaio, Vinicius Fernando Coelho. "Transition Metal-Substituted Potassium Silicotungstate Salts as Catalysts for Oxidation of Terpene Alcohols with Hydrogen Peroxide". . p. 2094 - 2106. Retrieved 2020/11/13.