Background
1-undecanol, being an organic chemical with molecular formula C11H24O and scented with lemon, is a colorless or pale yellow , water insoluble but alcohol and ether soluble liquid. It is prepared from metal sodium reduction of Ethyl undecanoate, or pressurization and catalytic hydrogenation of ethyl ω- undecanoate , or even obtained by the Grignard reaction of nonyl magnesium bromide and with ethylene oxide. The application of this alcohol is limited. It is only used for some typical aroma oil and fragrance as the fat is solid at low temperature. The citrus rose type and the like only play a secondary and harmonious role and are taken as deodorant. In addition, it is also used to manufacture spices with the scent of acacia, polianthes tuberosa and the like.
Chemical Properties
It is colorless liquid at room temperature; scented with light sweet fat wax mixed with the scent of roses and fruity flavor of citrus, pineapple and the like. But generally the whole body smells scent of rose, as if a little bit of rue flavor. It will smell like orange after highly diluted with the soft sweet flavor of citrus fruit oil. Its concentration is less than 20 × 10-6 with fruity and sweet scent. Unpleasant fat and smell will be produced when the concentration is higher; Melting point :15 ~ 19 ℃; Flash point> 82 ℃; Density: D4250 .828 ~ 0.834; Refractive index: nD200.4370 ~ 1.4430; water insoluble, soluble in most organic solvents, 1: 4.soluble in 60% ethanol
Preparation
It is prepared from undecaethylene reduction. Put 200 ml of anhydrous toluene and 70 g of sodium into a 5-liter three-necked flask, and then heat reflux it until sodium is completely melted. Then stop heating, stir quickly to get the sodium to disperse into sand until the temperature drops to 60 ~ C. Then put 107 grams of ethyl undecanoate into 150ml absolute ethanol solution followed by adding 500ml of absolute ethanol. When the reaction is weakened, heat it in an oil bath until the sodium is completely dissolved. Next remove the ethanol and toluene through the method of steam distillation. Then wash the remaining oily substances with 200ml × 3 hot water. Then wash ether layer with a sequence of water, sodium carbonate and then water after the ethyl ether was extracted. Also dry with magnesium sulfate, boil off the ethyl ether. The product will be finally extracted from the residue after reduced pressure distillation. The yield is 70%.
Uses
Although this undecanol is among the common varieties, but it is still not widely used. It is often used together with undecylenic aldenyde or other fat and aldehydes as the integrator of fragrant volatile of aldehyde. Also it can be well integrated with floral fragrance, citrus cologne, acacia, robinia pseudoacacia, tuberose, violets, clean and grass smell, usually used for rose base. Few application is also available in such pineapple, orange, lemon, lime, orange , cassis, rose food flavors.
Storage
Be sealed and stored in a cool dry place. Also be kept away from fire.
Chemical Properties
Colorless liquid; citrus odor. Soluble in 60% alcohol. Combustible.
Chemical Properties
Undecyl alcohol has a floral, citrus-like odor and fatty flavor.
Occurrence
Reported found in citrus fruits, fresh apple, banana, sour cherry, orange juice, orange peel oil, American
cranberry, Vitis vinifera L., parmesan cheese, mushroom, tamarind, coriander seed and leaf, white wine, butter, heated butter, boiled
eggs, boiled or uncured pork, plum brandy, coriander leaf, crayfish and oysters.
Uses
1-Undecanol is an antifungal, antioxidant compound. As well, it is used in the synthesis
Uses
1-Undecanol can be used as a precursor in the synthesis of undecanal by chemoselective oxidation using a fluorous derivative of TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) radical as a catalyst.
It can be also used as a solvent in homogeneous liquid-liquid microextraction method.
Preparation
By reduction of the corresponding aldehyde.
Definition
ChEBI: A fatty alcohol that is undecane substituted by a hydroxy group at position 1.
Synthesis Reference(s)
The Journal of Organic Chemistry, 60, p. 5961, 1995
DOI: 10.1021/jo00123a038
General Description
Undecyl alcohol has been reported as a key volatile constituent of
Senecio tenuifolius and
Flacourtia montana.
Health Hazard
Recommended Personal Protective Equipment: Goggles and face shield; Symptoms Following Exposure: Liquid can irritate eyes; General Treatment for Exposure: Wash eyes with water for at least 15 min.; Toxicity by Inhalation (Threshold Limit Value): Not pertinent; Short-Term Exposure Limits: Not pertinent; Toxicity by Ingestion: Grade 2, LD50 = 0.5-5 g/kg; Late Toxicity: Data not available; Vapor (Gas) Irritant Characteristics: None; Liquid or Solid Irritant Characteristics: No appreciable hazard. Practically harmless to the skin; Odor Threshold: Not pertinent.
Flammability and Explosibility
Non flammable
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Safety Profile
Moderately toxic by
ingestion. A skin irritant. Combustible
liquid. Mutation data reported. When heated
to decomposition it emits acrid smoke and
irritating fumes. See also ALCOHOLS.
Metabolism
See alcohol C-8.
Purification Methods
Purify the alcohol by repeated fractional crystallisation from its melt or by distillation in a vacuum. [Beilstein 1 H 427, 1 IV 1835.]
