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

(3,7-dimethyloct-6-enyloxy)trimethylsilane

C₂₄H₃₉NO₃

Refernces

Fragrance release from the surface of branched poly(amide)s

10.3390/10010081

The research investigates the use of hydrolytic enzymes, specifically a lipase from Candida cylindracea and a cutinase from Fusarium solani pisii, in the selective cleavage of ester groups on the peripheral layer of linear and branched polyamides conjugated to fragrances citronellol and L-menthol via ester linkages. The study explores the potential of these enzymes for post-synthetic modification of dendrimers and hyperbranched molecules. The polyamides were synthesized in a convergent fashion, and the hydrolysis studies were conducted in aqueous buffered systems under optimal conditions for the enzymes. Analytical techniques such as RP-HPLC, GC, and MALDI-TOF mass spectrometry were employed to monitor the alcohol release and identify hydrolytic products. The results revealed that the enzyme's ability to interact with the substrates decreased significantly with increased branching density, rigidity, and bulkiness of the polyamide-fragrance conjugates. The lipase showed limited efficacy, with notable ester cleavage only observed in one case, while the cutinase demonstrated more favorable interactions, particularly with linear polyamides.

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