123-11-5

odor

There is a strong anise-like aroma and hawthorn. It is fresh, green fennel aroma. The scent of the flower is like the Hawthorn flower, while the scent of the beans is like the scent of vanilla bean. It has some sweetness of herbs and spices. The fragrance is strong, and lasts for quite long time. There is stronger and clearer alcohol and rougher than anise. The above information is edited by the lookchem of Tian Ye.

Content Analysis

0.8g of anisaldehyde is accurately weighed, and determined according to the method of aldehyde and ketone determination (OT-7) or the method of determination of two or aldehyde (OT-6).The time of the reactional placement for samples and control samples are 1.5 minutes respectively. Calculation of the equivalent factor (E) is to take 68.08. Or it can be measured by gas chromatography (GT-10-4) nonpolar column method.

Toxicity

LD50 orally in rats: 1510 mg/kg (Jenner)

FEMA limits

FEMA (mg/kg): Soft drinks 6.3; cold drink 5.6; candy 14; baked goods 16; puddings class from 0.5 to 30; gum from 18 to 76.Moderate limit(FDA§172．515，2000).The concentration of the final product is generally 5~30mg/kg.

Production method

It can be obtained through p-cresol methyl ether from the p-cresol by methylation and then oxidation by adding manganese dioxide and sulfuric acid. Or it is derived from the oxidation of anisole. Anise aldehyde is mainly included in anise oil, fennel oil, dill oil, gold Albizia julibrissin oil, vanilla extract, etc. When extracted from natural raw materials, it is oxidated by ozone, nitric acid, potassium permanganate, sodium dichromate or sulfuric acid, in the presence of p-Aminobenzene Sulfonic. It can also be obtained as follows: Anethole is Isolated from the essential oil, then decomposed by yellow blood salt, water, sodium bisulfite and other appropriate decomposing agent, cutting off the allyl double bond and generating anise aldehyde. According to the method, the yield was 60%. It had been discovered and synthesized before it has been isolated from the essential oil. The product can be prepared to take from phenol and anisole, cresol ether, preparation of p-hydroxybenzaldehyde and other raw materials. Using dimethyl sulfate for methylation of phenol, followed by chloromethylation reaction Fennel introducing chloromethyl ether and Urotropine with salt, and then hydrolyzed to chloromethyl into aldehyde (Suo Mulai reaction) to prepare p-methoxy benzaldehyde. Another promising approach is to turn on the methylation of toluene, the formation of methyl phenyl ether, and then oxidation to obtain the production. In foreign countries, the current method is using oxidating p-methyl anisole in sulfuric acid in the presence of the oxidizing agent such as potassium dichromate, potassium permanganate and manganese dioxide.

Preparation

By methylation and oxidation of p-cresol and also by oxidation of anethole.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 42, p. 1041, 1994 DOI: 10.1248/cpb.42.1041Tetrahedron Letters, 43, p. 1395, 2002 DOI: 10.1016/S0040-4039(02)00027-8

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes

Metabolism

Anisic aldehyde undergoes a very slight degree of demethylation with oxidation of its aldehyde group to an acid group, the major metabolite excreted being anisic acid (Williams, 1959).

Purification Methods

Wash the aldehyde with saturated aqueous NaHCO3, then H2O, steam distil, extract the distillate with Et2O, dry (MgSO4) the extract, filter and distil this under a vacuum and N2. Store it in glass ampules under N2 in the dark. [Beilstein 8 IV 252.]

Sources and Industrial Applications

PAA is naturally occurring and is found in essential oils derived from seeds of Pimpinella anisum, anise, cumin, fennel, and garlic. It is widely used in the food, beverages, and pharmaceutical industries both as a final product and as an intermediate compound for other reactions. The industrial production of PAA typically involves the oxidation or methylation of p-cresol or anisole, often under hazardous conditions.

Antimicrobial Activity

PAA exhibits broad-spectrum antimicrobial activity against various microorganisms, including bacteria (Staphylococcus aureus, Bacillus subtilis, Listeria monocytogenes, Pseudomonas aeruginosa), yeasts (Candida, Saccharomyces cerevisiae), and molds (Aspergillus niger). It has been used for the preservation of fruits and vegetables due to its safety and antimicrobial properties.

Safety and Regulatory Status

The United States Food and Drug Administration (FDA) has categorized PAA as "generally recognized as safe" (GRAS) for its application in food products as a natural additive. Previous studies have demonstrated the safety and efficacy of PAA in inhibiting the growth of various pathogens, including Candida albicans, Penicillium italicum, Staphylococcus aureus, Listeria monocytogenes, and Pseudomonas aeruginosa.

Potential Applications

Recent research suggests potential applications of PAA in regulating postharvest physiological and biochemical behavior of horticultural products. Combinations of PAA with other substances, such as 尾-cyclodextrin, have shown effectiveness in suppressing the growth of fungi and preserving the storage quality of fruits like strawberries.

General Description

**p-Anisaldehyde** (also known as **p-methoxybenzaldehyde**, **4-anisaldehyde**, or **anisic aldehyde**) is an aromatic aldehyde characterized by a methoxy group (–OCH?) para to the formyl group (–CHO) on a benzene ring. It serves as a versatile intermediate in organic synthesis, particularly in the formation of heterocycles (e.g., oxazolidines, thiazolidines), reductive acetal ring-opening reactions, and enantioselective cyanohydrin formation. It is also used in biomimetic oxidation studies and as a precursor for bioactive molecules like indole alkaloids and diphenylhydroxyethylamines. Its reactivity with amino acid esters and role in catalytic systems highlight its utility in constructing complex chiral frameworks and sustainable chemical processes.

Product description

Anisaldehyde(Anisic aldehyde),also known as anisaldehyde,4-methoxybenzaldehyde, anisaldehyde, anise aldehyde, is colorless to pale yellow liquid at room temperature with a similar smell of hawthorn. Density 1.123g/cm3 (20 ℃). Melting point 2℃. The boiling point is 249.5. The refractive index is 1.5731. It is difficult to dissolve in water (solubility in water 0.3%), slightly soluble in propylene glycol, glycerin, soluble in ethanol, ether, acetone, chloroform and other most organic solvents. It can be volatiled with the steam. It exists in the oil of anise, fennel oil, dill oil, Acacia flowers, vanilla extract in nature, obtained by oxidation and separation. The synthesized methods are as follows:(1) Phenol is methylated with dimethyl sulfate, and then it is followed by the reaction of chlorine methylation, hydrolysis; (2) p-cresol is methylated and then obtained by further oxidized; (3) It can be obtained through methylation of p-hydroxybenzaldehyde. It is mainly used as flavor base of hawthorn, sunflower, lilac and other flavors, blending spices of new treasure, white gold Albizia julibrissin, Acacia, grass perfume and other flavors, co-flavoring agents of Lily fragrance and modified agent of sweet scented osmanthus flavor. Tetra (p-methoxyphenyl) porphyrin and cobalt complexes can be synthetized by methoxy benzaldehyde and pyrrole as raw materials, in the reaction system of propionic acid as solvent and chloroacetic acid as catalyst. As an excellent bright agent for non-cyanide zinc plating DE additive, it can improve the anodic polarization over a wide current range, get bright coating, to create favorable conditions for environmental protection. Anti-microbial drugs cefadroxil benzyl penicillin derived from anisaldehyde in the pharmaceutical industry for the manufacture is an intermediate of antihistamine drugs. It is allowed for the use of edible spices conformed to China's GB2760-86 regulations .It is mainly for the preparation of essence of vanilla, spices, apricot, cream, fennel, caramel, cherry, chocolate, walnuts, raspberry, strawberry, mint and so on. Methoxycinnamic aldehyde can be obtained through condensation of anisaldehyde and acetaldehyde in alkaline conditions.

Aroma threshold values

Aroma characteristics at 1.0%: sweet powdery, spicy creamy, fruity, vanilla and hay-like. Coumarin, almond, anisic with berry nuances.

Taste threshold values

Taste characteristics at 5 to 10 ppm: sweet powdery, vanilla creamy, spice anise, nutty, cherry pit and almond-like nuances.