Neral

Base Information

• Chemical Name: Neral
• CAS No.: 106-26-3
• Deprecated CAS: 1208977-81-4
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• European Community (EC) Number: 203-379-2
• UNII: 8M466BQL1X
• DSSTox Substance ID: DTXSID60881216
• Nikkaji Number: J3.242E
• Wikidata: Q27104033
• RXCUI: 1484865
• Metabolomics Workbench ID: 28005
• Mol file: 106-26-3.mol

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

Chemical Property of Neral

Chemical Property:

• Vapor Pressure: 0.0712mmHg at 25°C
• Refractive Index: nD20 1.4869
• Boiling Point: 229°Cat760mmHg
• Flash Point: 101.7°C
• PSA: 17.07000
• Density: 0.856g/cm³
• LogP: 2.87800
• Water Solubility.: 289mg/L(25 oC)
• 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:

99.9% ^*data from raw suppliers

(2Z)-3,7-dimethylocta-2,6-dienal 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CC=O)C)C
• Isomeric SMILES: CC(=CCC/C(=C\C=O)/C)C
• Uses: In the synthesis of vitamin A, ionone and methylionone. As a flavor and in perfumery for its citrus effect.

Technology Process of Neral

There total 73 articles about Neral 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: 100.0%

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

Guidance literature:

With oxygen; Pd₅₆₁phen60(OAc)180; In acetic acid; benzene; at 60 ℃; for 24h;

DOI:10.1016/S0040-4039(97)10411-7

Reference yield: 95.0%

citral oxime (172161-70-5) → cis-3,7-dimethyl-2,6-octadienal (106-26-3,96680-15-8)

Guidance literature:

With perchloric acid; dihydrogen peroxide; potassium bromide; ammonium molybdate tetrahydrate; In water; at 20 ℃; for 1.5h;

DOI:10.1055/s-2008-1032035

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;

upstream raw materials:

geranyl bromide

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

Nerol

Geraniol

Downstream raw materials:

pseudoionone

(6E,8Z,10Z)-2,6,11,15-tetramethyl-hexadeca-2,6,8,10,14-pentaene

(6E,8E,10Z)-2,6,11,15-tetramethyl-hexadeca-2,6,8,10,14-pentaene

4,6-bis(4-methylpent-3-en-1-yl)-6-methylcyclohexa-1,3-diene-1-carbaldehyde

Refernces

• 1、 Hirano, Masao,Nagasawa, Sonoko,Morimoto, Takashi. "A Convenient Preparation of Ketones by the Oxidation of Secondary Alcohols with Chromium(VI) Trioxide in Aprotic Solvent in the Presence of "Wet"-Aluminium Oxide". . p. 2857 - 2859. Retrieved 1991.
• 2、 Kanemoto, Shigekazu,Oshima, Koichiro,Matsubara, Seijiro,Takai, Kazuhiko,Nozaki, Hitosi. "TRANSITION-METAL CATALYZED OXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES BY MEANS OF Me3SiOOSiMe3". . p. 2185 - 2188. Retrieved 1983.
• 3、 Kaneda, Kiyotomi,Fujie, Yoko,Ebitani, Kohki. "Catalysis of giant palladium cluster complexes, highly selective oxidations of primary allylic alcohols to (α,β-unsaturated aldehydes in the presence of molecular oxygen". . p. 9023 - 9026. Retrieved 1997.
• 4、 Wang, Weiwei,Zhang, Xiaoteng,Zhao, Yu,Liu, Xinlei,Zhang, Zhenhua,Wang, Mingan. "Divergent synthesis of four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid, esters and evaluation for the antifungal activity". . . Retrieved 2018.
• 5、 Ying, Xiangxian,Yu, Shihua,Huang, Meijuan,Wei, Ran,Meng, Shumin,Cheng, Feng,Yu, Meilan,Ying, Meirong,Zhao, Man,Wang, Zhao. "Engineering the enantioselectivity of yeast old yellow enzyme Oye2Y in asymmetric reduction of (E/Z)-citral to (R)-citronellal". . . Retrieved 2019.
• 6、 Wang, Yong-Huan,Cong, Hang,Zhao, Fang-Fang,Xue, Sai-Feng,Tao, Zhu,Zhu, Qian-Jiang,Wei, Gang. "Selective catalysis for the oxidation of alcohols to aldehydes in the presence of cucurbit[8]uril". . p. 1127 - 1130. Retrieved 2011.
• 7、 Martinez, Luis A.,Garcia, Olivia,Delgado, Francisco,Alvarez, Cecilio,Patino, Rocio. "Oxydation d'Alcools Benzyliques et Allyliques par le systeme MnO2/Bentonite sous irradiation aux micro-ondes ou ultrasons en absence de solvant.". . p. 5293 - 5294. Retrieved 1993.
• 8、 Baro, Angelika,Dallavalle, Sabrina,Hasnik, Fabian,Laschat, Sabine,Sinast, Moritz,Sube, Tobias,Wischnat, Jonathan,Zuccolo, Marco. "Samarium Iodide-Promoted Asymmetric Reformatsky Reaction of 3-(2-Haloacyl)-2-oxazolidinones with Enals". . . Retrieved 2019.
• 9、 Anikeev,Ermakova,Chibiryaev,Kozhevnikov. "Kinetics of thermal conversions of monoterpenic compounds in supercritical lower alcohols". . p. 162 - 193. Retrieved 2010.
• 10、 Di Mola, Antonia,Massa, Antonio,De Feo, Vincenzo,Basile, Anna,Pascale, Maria,Aquino, Rita Patrizia,De Caprariis, Paolo. "Effect of citral and citral related compounds on viability of pancreatic and human B-lymphoma cell lines". . p. 631 - 639. Retrieved 2017.