Citral

Base Information

• Chemical Name: Citral
• CAS No.: 141-27-5
• Deprecated CAS: 37350-34-8,8022-94-4,96680-15-8,250599-19-0,433282-33-8,1392408-16-0,2321523-57-1
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• European Community (EC) Number: 205-476-5,226-394-6
• ICSC Number: 1725
• NSC Number: 6170
• UN Number: 2810
• UNII: 758ZMW724E
• DSSTox Substance ID: DTXSID20881217
• Nikkaji Number: J2.026E,J3.073B
• Wikipedia: Citral
• Wikidata: Q410888
• RXCUI: 1362890
• Pharos Ligand ID: C5NTZQNZ98C8
• Metabolomics Workbench ID: 28003
• ChEMBL ID: CHEMBL1080997
• Mol file: 141-27-5.mol

Synonyms:(E)-citral;(Z)-citral;citral;citral A;citral B;geranial;neral

Chemical Property of Citral

Chemical Property:

• Vapor Pressure: 0.0712mmHg at 25°C
• Refractive Index: nD20 1.4898
• Boiling Point: 229°Cat760mmHg
• Flash Point: 101.7°C
• PSA: 17.07000
• Density: 0.856g/cm³
• LogP: 2.87800
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethanol (Slightly)
• 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
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

α-Citral ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(=CCCC(=CC=O)C)C
• Isomeric SMILES: CC(=CCC/C(=C/C=O)/C)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the skin.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: α-Citral is an intermediate in the synthesis of 4,8-Dimethyl-1,3(E),7-nonatriene (D475810), which is a volatile compound released by corn plants in response to predation.

Technology Process of Citral

There total 95 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: 94.0%

Geraniol (106-24-1) → [3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methanol (50727-94-1) + 3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8)

Guidance literature:

With tert.-butylhydroperoxide; 4 A molecular sieve; ytterbium(III) isopropoxide; In dichloromethane; at 0 ℃; for 24h; also with La(Oi-Pr)3, Ce(Oi-Pr)3, Sm(Oi-Pr)3;

DOI:10.1016/S0040-4039(00)79922-9

Reference yield: 94.0%

Nerol (106-25-2) → cis-3,7-dimethyl-2,6-octadienal (106-26-3,96680-15-8) + 3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8)

Guidance literature:

With sodium hydroxide; dipotassium peroxodisulfate; nickel(II) sulphate; In dichloromethane; water; for 24h; Yields of byproduct given; Ambient temperature;

Reference yield: 73.6%

{[(2E)-3.7-dimethyl-2,6-octadien-1-yl]oxy}(triethyl)silane (160882-63-3) → 3,7-dimethyl-2,6-octadienal (141-27-5,96680-15-8) + Geraniol (106-24-1)

Guidance literature:

With water; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 0.75h;

DOI:10.1021/ol025946n

upstream raw materials:

geranyl bromide

3,7-dimethylocta-1,6-dien-3-ol

Nerol

Geraniol

Downstream raw materials:

5,9-dimethyl-2-phenyl-deca-2ξ,4t,8-trienoic acid

3,7-dimethyl-octa-2t,6-dienal-(2,4-dinitro-phenylhydrazone)

1-phenyl-3,7-dimethyl-2,6-octadiene

(E)-4,8-dimethylnona-1,3,7-triene

Refernces

• 1、 Hirano, Masao,Yakabe, Sigetaka,Chikamori, Hideki,Clark, James H.,Morimoto, Takashi. "Oxidation by Chemical Manganese Dioxide. Part 3.1 Oxidation of Benzylic and Allylic Alcohols, Hydroxyarenes and Aminoarenes". . p. 770 - 771. Retrieved 1998.
• 2、 Chaudhuri, Mihir K.,Dehury, Sanjay K.,Hussain, Sahid,Duarah, Ankur,Gogoi, Nayanmoni,Lakshmi Kantam. "3,5-dimethylpyrazolium fluorochromate(VI)-catalysed oxidation of organic substrates by hydrogen peroxide under solvent-free conditions". . p. 1349 - 1352. Retrieved 2005.
• 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 2021.
• 4、 Matano, Yoshihiro,Hisanaga, Teppei,Yamada, Hisatsugu,Kusakabe, Shingo,Nomura, Hazumi,Imahori, Hiroshi. "Remarkable substituent effects on the oxidizing ability of triarylbismuth dichlorides in alcohol oxidation". . p. 8676 - 8680. Retrieved 2004.
• 5、 Yokoyama, Toshiro,Nishizawa, Masato,Kimura, Tetsuo,Suzuki, Toshishige M.. "POLYMER-ANCHORED VANADIUM(V) AND MOLYBDENUM(VI) CATALYSTS FOR THE REGIOSELECTIVE EPOXIDATION OF (E)-GERANIOL WITH t-BUTYL HYDROPEROXIDE". . p. 1703 - 1706. Retrieved 1983.
• 6、 -. "An alkenate compound containing an aromatic ring and its preparation and application". Paragraph 0049-0052. . Retrieved 2022/01/04.