105-13-5

Star anise oil

Star anise oil, also known as anise oil, appears as colorless transparent or light yellow liquid at above 20°C. When the temperature will drop, there will be sheet crystal precipitate with anise aroma and sweetness of the anethole. It is slightly soluble in water and easily soluble in ethanol, ether and chloroform. It belongs to Illicium Linn, magnoliaceae. The fruit is an aggregate fruit, being octagonal, therefore it is commonly known as star anise, also known as aniseed. Star anise oil is a kind of aromatic oil with complex composition, being volatile oil and a little sticky. Its color is gray for the best case while is yellow for slightly worse cases. It tastes sweet and tingling with a strong aroma of star anise. It is agitated at a temperature of 10 to 15 °C upon stirring. Its main ingredient is trans-anethole with a content of up to 80%. It also contains α-pinene, limonene, linalool, safrole, anisic aldehyde, anisone, 4-terpineol, artemisia capillaris, anisaldehyde and other ingredients. Anise oil is a kind of aromatic oil which is strongly technical and is not easy to identify using chemical equipment. The current producing area is still mainly through the buyer with the naked eye and nose smell to identify the quality of star anise. Anise oil, in the spice industry, is mainly used to extract anethole brain and re-synthesis of anisaldehyde and anisol alcohol (p-methoxybenzyl alcohol, 4-methoxybenzyl alcohol). Some of the spices are widely used in toothpaste, food and soap and cosmetics fragrance. The fruit is commonly used in people's food seasoning spices. At the same time, the anise oil is the major raw material for the synthesis of negative hormone estrone in the pharmaceutical industry. As the octagonal oil is lighter than water, so it can be suspended in the water. The water obtained after oil and water separation contains anise oil after the anise oil returns to the distillation pot for re-distillation to improve the oil yield.

Content analysis

According to the Total Alcohol Assay (OT-5): the amount of acetylated alcohol used for saponification was 1.5 g. The equivalent factor (e) in the calculation is 69.09, or by gas chromatographic nonpolar column method in GT-10-4.

Toxicity

ADI 1 mg/kg (CE); LD50 1200 mg/kg (rat, oral);

Usage limit

FEMA (mg/kg): soft drink 7.4; cold drink 8.0; candy 11; baked goods 12; pudding class 1.9. Take moderate as limit (FDA § 172.515, 2000).

Production method

It is obtained through the anisaldehyde reduction. The anise, formaldehyde and sodium hydroxide are subject to Cannizzaro reaction in the ethanol to generate p-methoxybenzyl alcohol. After distilling to recycle the ethanol, the resulting oil layer is extracted with benzene, acidified with acetic acid, neutralized by sodium hydrogencarbonate to a weak basicity, washed with water to neutral, then distillation to recover benzene with the residue subjecting to distillation under reduced pressure to obtain p-methoxy Benzyl alcohol. In methanol solution, apply potassium hydroxide solution for treatment of the mixture of anisaldehyde and formaldehyde, getting mixture of anole alcohol and formic acid. Apply benzene extraction and then purify through distillation. Use platinum as a catalyst and ferrous chloride as a reductant, obtain it through anisidine hydrogenation.

Preparation

By reduction from anisic aldehyde

Synthesis Reference(s)

Synthetic Communications, 18, p. 613, 1988 DOI: 10.1080/00397918808064019Tetrahedron Letters, 32, p. 3243, 1991 DOI: 10.1016/S0040-4039(00)79734-6

Hazard

Extremely toxic.

Contact allergens

As a fragrance allergen, anisyl alcohol has to be mentioned by name in cosmetics within the EU.

Safety Profile

Moderately toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALCOHOLS.

Chemical properties

It appears as colorless to slightly yellow liquid or opaque crystals with the relative density of 1.110-1.120, refractive index of 1.543-1.545, the boiling point of about 258-259 °C, freezing point> 23.5 °C, the flash point of 100 °C above and insoluble in water. It is soluble in the same volume of 50% alcohol with an acidity value of 1.0. It mainly has fennel aroma with a slight cream fragrance and fragrant background. Aromatic odor is mild and can stay long.

Taste threshold values

Taste characteristics at 10 ppm: spice, anise, vanilla, balsamic and powdery

General Description

Anisyl alcohol is a volatile aromatic compound mainly found in vanilla extracts and anise oil. It is used as a flavoring agent and fragrance ingredient.