Citronellol

Base Information

• Chemical Name: Citronellol
• CAS No.: 106-22-9
• Deprecated CAS: 1335-43-9,26489-01-0
• Molecular Formula: C10H20O
• Molecular Weight: 156.268
• Hs Code.: 2905.22
• European Community (EC) Number: 203-375-0
• NSC Number: 8779
• UNII: 565OK72VNF
• DSSTox Substance ID: DTXSID3026726
• Nikkaji Number: J3.238G
• Wikipedia: Citronellol
• Wikidata: Q27122080
• RXCUI: 1424650
• Metabolomics Workbench ID: 133457
• ChEMBL ID: CHEMBL395827
• Mol file: 106-22-9.mol

Synonyms:beta-citronellol;citronellol;citronellol, (+-)-isomer;citronellol, (R)-isomer;citronellol, (S)-isomer;citronellol, titanium (+4) salt

Chemical Property of Citronellol

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.0183mmHg at 25°C
• Melting Point: 77-83 °C(lit.)
• Refractive Index: 1.462
• Boiling Point: 224.499 °C at 760 mmHg
• PKA: 15.13±0.10(Predicted)
• Flash Point: 98.333 °C
• PSA: 20.23000
• Density: 0.845 g/cm³
• LogP: 2.75130
• Storage Temp.: 2-8°C
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 156.151415257
• Heavy Atom Count: 11
• Complexity: 112

Purity/Quality:

99% ^*data from raw suppliers

rac-Citronellol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(CCC=C(C)C)CCO
• Description: Citronellol is a kind of natural occurring acyclic monoterpenoid which can be found in citronella oils such as Cymbopogon nardus ((+)-citronellol) and rose oils and Pelargonium geraniums ((-)-citronellol). In addition to be extracted from natural oils, it can also be manufactured by the hydrogenation of geraniol or nerol. It is mainly used in perfumes and insects repellents as well as being used as a mite attractant. It should be noted that it is an excellent mosquito repellent at short distances. Combination with beta-cyclodextrin can make it has an average duration time of 1.5 hour against the mosquitoes. It can also be used for the manufacture of rose oxide. One of its most common applications is for adding floral and citrus notes to perfumes, soaps and cosmetics.
• Uses: Perfumery, flavoring agent. citronellol is a constituent of plant essential oils. Found abundantly in eucalyptus oil. It is used for masking odor or providing a fragrance component to a cosmetic product. rac-Citronellol is a monoterpene found in the essential oil of various plants with antihypertensive properties. It possesses hypotensive actions due to its vasodilator abilities and is a phytochemical used in perfumes and insect repellents.

Technology Process of Citronellol

There total 180 articles about Citronellol 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: 89.0%

(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) + menthol (15356-70-4)

Guidance literature:

With hydrogen; In tert-butyl alcohol; at 80 ℃; for 8h; under 1500.15 - 15001.5 Torr; diastereoselective reaction; Autoclave;

DOI:10.1002/chem.200801776

Reference yield: 88.0%

(E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8) → Citronellol (106-22-9) + geraniol (624-15-7)

Guidance literature:

With hydrogen; silver; In tetrahydrofuran; at 150 ℃; for 72h; under 11251.1 Torr;

Reference yield: 88.0%

3,7-dimethyl-3,6-octadienal (1754-00-3,55722-59-3) → Citronellol (106-22-9) + geraniol (624-15-7)

Guidance literature:

With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; sodium formate; In water; at 80 ℃; for 0.5h; chemoselective reaction; Schlenk technique;

DOI:10.1021/acs.organomet.9b00353

upstream raw materials:

(R)-Citronellal

aluminum isopropoxide

3,7-dimethyl-oct-6-enal

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

Downstream raw materials:

tetrahydrogeraniol

citronellylbromide

citronellyl (4-methylbenzyl) ether

β-citronellol methyl ether

Refernces

• 1、 Friedfeld, Max R.,Margulieux, Grant W.,Schaefer, Brian A.,Chirik, Paul J.. "Bis(phosphine)cobalt dialkyl complexes for directed catalytic alkene hydrogenation". . p. 13178 - 13181. Retrieved 2014.
• 2、 da Silva, Aderivaldo P.,Mota, Saulo D.C.,Bieber, Lothar W.,Navarro, Marcelo. "Homogeneous electro-mediated reduction of unsaturated compounds using Ni and Fe as mediators in DMF". . p. 5435 - 5440. Retrieved 2006.
• 3、 Joo, Ferenc,Benyei, Attila. "Biphasic reduction of unsaturated aldehydes to unsaturated alcohols by ruthenium complex-catalyzed hydrogen transfer". . p. C19 - C21. Retrieved 1989.
• 4、 Kathó, ágnes,Szatmári, Imre,Papp, Gábor,Joó, Ferenc. "Effect of 2-propanol on the transfer hydrogenation of aldehydes by aqueous sodium formate using a rhodium(i)-sulfonated triphenylphosphine catalyst". . p. 339 - 344. Retrieved 2015.
• 5、 Gieck, Christine,Schreyer, Martin,Faessler, Thomas F.,Cavet, Sylwia,Claus, Peter. "Synthesis, crystal structure, and catalytic properties of MgCo 6Ge6". . p. 1924 - 1930. Retrieved 2006.
• 6、 Milone,Tropeano,Gulino,Neri,Ingoglia,Galvagno. "Selective liquid phase hydrogenation of citral on Au/Fe2O3 catalysts". . p. 868 - 869. Retrieved 2002.
• 7、 Hidai,M. et al.. "-". . p. 170 - 171. Retrieved 1975.
• 8、 Kantam, M. Lakshmi,Rao, B. Purna Chandra,Choudary,Sreedhar. "Selective transfer hydrogenation of carbonyl compounds by ruthenium nanoclusters supported on alkali-exchanged zeolite beta". . p. 1970 - 1976. Retrieved 2006.
• 9、 Trasarti,Marchi,Apesteguia. "Design of catalyst systems for the one-pot synthesis of menthols from citral". . p. 155 - 165. Retrieved 2007.
• 10、 Enholm, Eric J.,Prasad, Girija. "TRIBUTYLTIN HYDRIDE-INDUCED O-STANNYL KETYLS IN THE CYCLIZATION OF ALDEHYDES AND KETONES WITH ALKENES". . p. 4939 - 4942. Retrieved 1989.