Citronellol

Citronellol Basic information
Product Name:Citronellol
Synonyms:(+/-)-CITRONELLOL;CITRONELLOL;CITRONELLOL PRIME;CITRONELLOL 90/92;CITRONELLOL 96/98;CITRONELLOL AJ;CITRONELLOL, DL-B-;DL-B-CITRONELLOL
CAS:106-22-9
MF:C10H20O
MW:156.27
EINECS:203-375-0
Product Categories:Acyclic;Alcohols;Alkenes;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Alphabetical Listings;C-D;Acyclic Monoterpenes;Biochemistry;Terpenes;Flavors and Fragrances;bc0001
Mol File:106-22-9.mol
Citronellol Structure
Citronellol Chemical Properties
Melting point 77-83 °C(lit.)
Boiling point 225 °C(lit.)
alpha -0.3~+0.3°(D/20℃)(neat)
density 0.857 g/mL at 25 °C(lit.)
vapor density 5.4 (vs air)
vapor pressure ~0.02 mm Hg ( 25 °C)
refractive index n20/D 1.456(lit.)
FEMA 2309 | DL-CITRONELLOL
Fp 209 °F
storage temp. 2-8°C
solubility Chloroform, Methanol (Sparingly)
pka15.13±0.10(Predicted)
form Liquid
color Clear almost colorless
Odorat 100.00 %. floral leather waxy rose bud citrus
Odor Typefloral
Water Solubility SLIGHTLY SOLUBLE
Merck 14,2330
JECFA Number1219
BRN 1721507
Stability:Stable. Incompatible with oxidizing agents.
InChIKeyQMVPMAAFGQKVCJ-UHFFFAOYSA-N
LogP3.41 at 25℃
CAS DataBase Reference106-22-9(CAS DataBase Reference)
NIST Chemistry Reference6-Octen-1-ol, 3,7-dimethyl-(106-22-9)
EPA Substance Registry SystemCitronellol (106-22-9)
Safety Information
Hazard Codes Xi,N
Risk Statements 36/37/38-51/53-43-36/38
Safety Statements 26-36-24/25-61-37-24
WGK Germany 1
RTECS RH3400000
Hazard Note Irritant
TSCA Yes
HS Code 29052220
Hazardous Substances Data106-22-9(Hazardous Substances Data)
toxicityThe acute oral LD50 value in rats was reported as 3.45 g/kg (3.21-3.69 g/kg) (Moreno, 1973). The acute dermal LE>50 value in rabbits was reported as 2.65 g/kg (1.78-3.52 g/kg) (Moreno, 1973). The im LD50 value in mice was reported as 4 g/kg (Northover & Verghese, 1962).
MSDS Information
ProviderLanguage
CitronellolEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
Citronellol Usage And Synthesis
DescriptionCitronellol 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.
Chemical Propertiescolourless liquid with a characteristic, rose-like, smell
Chemical PropertiesCitronellol has a characteristic rose-like odor. Because odor plays such an important part in selecting this material, there may be special grades of citronellol that do not meet the Essential Oil Association specification. These limits have been broadened enough to include best qualities of commercial citronellol and chemically pure citronellol. l-Citronellol has a sweet, peach-like flavor; d-citronellol has a bitter taste.
Occurrencel-Citronellol has been found in the plants of the Rosaceae family; d- and dl-citronellol have been identified in Verbenaceae, Labiatae, Rutaceae, Geraniaceae and others; citronellol has been reported in about 70 essential oils and in the oil of Rosa bourbonia; the Bulgarian rose oil has been reported to contain more than 50% l-citronellol, whereas East African geranium contains more than 80% of the d-isomer; the natural product is always optically active. Reported found in guava fruit, orange, bilberry, blackcurrant, nutmeg, ginger, corn mint oil (Mentha arvensis L. var. piperascens), mustard, pennyroyal oil (Mentha pulegium L.), hop oil, tea, coriander seed, cardamom, beer, rum, and apple juice.
Usescitronellol 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.
UsesPerfumery, flavoring agent.
Usesrac-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.
PreparationBy reduction of citronellal or geraniol or by fractional distillation of such essential oils as geranium and citronella (Bedoukian, 1967).
DefinitionChEBI: A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.
Aroma threshold valuesDetection at 11 ppb to 2.2 ppm; l-form, 40 ppb
Taste threshold valuesTaste characteristics at 20 ppm: floral, rose, sweet and green with fruity citrus nuances.
Synthesis Reference(s)The Journal of Organic Chemistry, 60, p. 2260, 1995 DOI: 10.1021/jo00112a056
Synthesis, p. 391, 1976
Tetrahedron Letters, 30, p. 5677, 1989 DOI: 10.1016/S0040-4039(00)76168-5
General DescriptionCitronellol is a volatile monoterpenic primary alcohol mainly found in the essential oil of plants such as Pelargonium graveolensCymbopogon winterianusand Rosa damascena. It is also one of the glycosidically bound aroma compounds in ginger.
Flammability and ExplosibilityNonflammable
Safety ProfilePoison by intravenous route. Moderately toxic by ingestion, skin contact, and intramuscular routes. A severe skin irritant. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALCOHOLS.
SynthesisIt is generally accepted to distinguish rhodinol as the product isolated from geranium consisting of a mixture of l-citronellol and geraniol, whereas the name l-citronellol should be used to indicate the corresponding synthetic product with the highest level of purity; dl-citronellol can be prepared by catalytic hydrogenation of geraniol or by oxidation of allo-cyrnene; l-citronellol is prepared from (+) d-pinene via (+) cis-pinene to (+) 2,6-dimethyl-2,7-octadiene and, finally, isolating l-citronellol by hydrolysis of the aluminum-organo compound.
Purification MethodsPurify them bydistillation through a cannon packed (Ni) column and the main cut collected at 84o/14mm and redistilled. Also purify via the benzoate. [IR: Eschenazi J Org Chem 26 3072 1961, Naves Bull Soc Chim Fr 505 1951, Beilstein 1 IV 2188.]
Referenceshttps://eic.rsc.org/magnificent-molecules/citronellol/2000020.article
https://en.wikipedia.org/wiki/Citronellol
Citronellol Preparation Products And Raw materials
Raw materialsEthanol–>Hydrogen–>tert-Butanol–>Ferrous sulfate heptahydrate–>Citral–>Geraniol–>Citronellal–>NEROL–>ALPHA-PINENE–>Diisobutylaluminium hydride–>Eucalyptus oil–>Citronella oil–>Triisobutylaluminium–>Platinum balck–>Dihydromyrcene–>Citronellol –dextro–>ISOPULEGOL
Preparation ProductsGeraniol–>Citronellal–>CITRONELLIC ACID–>Rose Oil–>Rhodinol–>Citronellyl acetate–>CITRONELLYL ISOBUTYRATE–>3,7-DIMETHYL-1-OCTANOL

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