Citronellal

Base Information

• Chemical Name: Citronellal
• CAS No.: 106-23-0
• Deprecated CAS: 26489-02-1
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• Hs Code.: 29121900
• European Community (EC) Number: 203-376-6,932-317-3
• NSC Number: 46106
• UNII: QB99VZZ7GZ
• DSSTox Substance ID: DTXSID3041790
• Nikkaji Number: J3.239E
• Wikipedia: Citronellal
• Wikidata: Q61651085
• Metabolomics Workbench ID: 134561
• ChEMBL ID: CHEMBL447944
• Mol file: 106-23-0.mol

Synonyms:citronellal;citronellal, (+-)-isomer;citronellal, (R)-isomer;citronellal, (S)-isomer

Chemical Property of Citronellal

Chemical Property:

• Appearance/Colour: clear light yellow liquid
• Vapor Pressure: 0.215mmHg at 25°C
• Melting Point: -16°C (estimate)
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 208.4 °C at 760 mmHg
• Flash Point: 75.6 °C
• PSA: 17.07000
• Density: 0.85 g/cm³
• LogP: 2.95790
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly miscible with water and ethanol.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 132

Purity/Quality:

99% ^*data from raw suppliers

rac-Citronellal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; Xn; N
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(CCC=C(C)C)CC=O
• Uses: rac-Citronellal is a monoterpenoid and the major isolate in citronella oil. Citronella oil is an essential oil bearing insecticidal properties. rac-Citronellal is also often used as a fragrance ingred ient. citronella is used primarily as a fragrance (perfuming and masking), it also has tonic properties. It is derived from the essential oil of the Cymbopogon nardus plant, and its constituents include geraniol (approximately 60 percent), citronellal, camphene, limonene, linalool, and borneol. Citronellal is a flavoring agent that is a liquid, faintly yellow with an intense odor resembling lemon, citronella, and rose. it is soluble in alcohol and most fixed oils, slightly soluble in mineral oil and pro- pylene glycol, and insoluble in water and glycerin. it is obtained by chemical synthesis; the aldehyde may be obtained from natural oils, such as citronella oil. it is also termed 3,7-dimethyl-6-octen-1-a1.

Technology Process of Citronellal

There total 103 articles about Citronellal 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: 70.0%

(+/-)-3,7-dimethyloct-6-enyl 2-oxo-2-phenylacetate (191750-82-0) → 3,7-dimethyl-oct-6-enal (106-23-0,26489-02-1) + benzaldehyde (100-52-7) + (1S,9R)-6,10,10-Trimethyl-1-phenyl-3,11-dioxa-bicyclo[7.2.0]undecan-2-one

Guidance literature:

In benzene; Irradiation;

DOI:10.1021/jo970912s

Reference yield: 54.0%

Geraniol (106-24-1) → 3,7-dimethyl-oct-6-enal (106-23-0,26489-02-1) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8)

Guidance literature:

With C₅₆H₈₂N₈O₂₀S₂; In benzene; at 20 ℃; for 2.5h; Irradiation;

DOI:10.1246/bcsj.81.361

Reference yield: 34.0%

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8) → Citronellol (106-22-9) + tetrahydrogeraniol (106-21-8,59204-02-3) + 3,7-dimethyl-oct-6-enal (106-23-0,26489-02-1) + menthol (15356-70-4) + isopulegol (89-79-2,7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8)

Guidance literature:

With hydrogen; In tert-butyl alcohol; at 80 ℃; for 8h; under 15001.5 Torr; diastereoselective reaction; Autoclave;

DOI:10.1002/chem.200801776

upstream raw materials:

(3R)-citronellol

(E/Z)-3,7-dimethyl-2,6-octadienal

Geraniol

methanol

Downstream raw materials:

4,8-dimethyl-7-nonen-2-ol

benzyl-(3,7-dimethyl-oct-6-enylidene)-amine

(E)-6,10-dimethylundeca-3,9-dien-2-one

3,7-dimethyl-oct-6-enal-dimethylacetal

Refernces

• 1、 Antonels, Nathan Charles,Meijboom, Reinout. "Preparation of well-defined dendrimer encapsulated ruthenium nanoparticles and their application as catalyst and enhancement of activity when utilised as SCILL catalysts in the hydrogenation of citral". . p. 148 - 152. Retrieved 2014.
• 2、 Matano,Nomura. "Dimeric triarylbismuthane oxide: A novel efficient oxidant for the conversion of alcohols to carbonyl compounds". . p. 6443 - 6444. Retrieved 2001.
• 3、 Assal, Mohamed E.,Shaik, Mohammed Rafi,Kuniyil, Mufsir,Khan, Mujeeb,Al-Warthan, Abdulrahman,Siddiqui, Mohammed Rafiq H.,Khan, Sohail M. A.,Tremel, Wolfgang,Tahir, Muhammad Nawaz,Adil, Syed Farooq. "A highly reduced graphene oxide/ZrOx-MnCO3 or -Mn2O3 nanocomposite as an efficient catalyst for selective aerial oxidation of benzylic alcohols". . p. 55336 - 55349. Retrieved 2017.
• 4、 Carari, Danieli M.,Da Silva, Marcio J.. "A highly selective Pd(OAc)2/pyridine/K2CO3 system for oxidation of terpenic alcohols by dioxygen". . p. 251 - 258. Retrieved 2012.
• 5、 Litthauer,Gargiulo,Van Heerden,Hollmann,Opperman. "Heterologous expression and characterization of the ene-reductases from Deinococcus radiodurans and Ralstonia metallidurans". . p. 89 - 95. Retrieved 2014.
• 6、 Liu, Ruixia,Yu, Yancun,Yoshida, Kazuki,Li, Guiming,Jiang, Haoxi,Zhang, Minhua,Zhao, Fengyu,Fujita, Shin-ichiro,Arai, Masahiko. "Physically and chemically mixed TiO2-supported Pd and Au catalysts: unexpected synergistic effects on selective hydrogenation of citral in supercritical CO2". . p. 191 - 200. Retrieved 2010.
• 7、 Burgener, Marco,Wirz, Ronny,Mallat, Tamas,Baiker, Alfons. "Nature of catalyst deactivation during citral hydrogenation: A catalytic and ATR-IR study". . p. 152 - 161. Retrieved 2004.
• 8、 Lagerspets, Emi,Lagerblom, Kalle,Heli?vaara, Eeva,Hiltunen, Otto-Matti,Moslova, Karina,Nieger, Martin,Repo, Timo. "Schiff base Cu(I) catalyst for aerobic oxidation of primary alcohols". . p. 75 - 79. Retrieved 2019.
• 9、 Corey,E.J.,Suggs,J.W.. "-". . p. 2647 - 2650. Retrieved 1975.
• 10、 Paul, Caroline E.,Gargiulo, Serena,Opperman, Diederik J.,Lavandera, Iván,Gotor-Fernández, Vicente,Gotor, Vicente,Taglieber, Andreas,Arends, Isabel W. C. E.,Hollmann, Frank. "Mimicking nature: Synthetic nicotinamide cofactors for C=C bioreduction using enoate reductases". . p. 180 - 183. Retrieved 2013.