p-Anisaldehyde Chemical Properties

Melting point:

-1 °C

Boiling point:

248 °C(lit.)

Density 

1.121

vapor density 

4.7 (vs air)

vapor pressure 

<1 hPa (20 °C)

FEMA 

2670 | P-METHOXYBENZALDEHYDE

refractive index 

n20/D 1.573(lit.)

Flash point:

228 °F

storage temp. 

Store below +30°C.

solubility 

2g/l

form 

Liquid

color 

Clear colorless to yellow

PH

7 (2g/l, H2O, 20℃)

Odor

sweetish odor

Odor Type

anisic

explosive limit

1.4-5.3%(V)

Water Solubility 

Miscible with acetone, alcohol, ether, chloroform and benzene. Immiscible with water.

Sensitive 

Air Sensitive

Decomposition 

> 160°C

Merck 

14,663

JECFA Number

878

BRN 

471382

InChIKey

ZRSNZINYAWTAHE-UHFFFAOYSA-N

LogP

1.56 at 25℃

CAS DataBase Reference

123-11-5(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 4-methoxy-(123-11-5)

EPA Substance Registry System

Benzaldehyde, 4-methoxy- (123-11-5)

Safety Information

Hazard Codes 

Xn,Xi,T,F

Risk Statements 

22-36/37/38-39/23/24/25-23/24/25-11-R22-36/38

Safety Statements 

26-36-45-36/37-16-7

WGK Germany 

1

RTECS 

BZ2625000

F 

10-23

Autoignition Temperature

220 °C

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29124900

Hazardous Substances Data

123-11-5(Hazardous Substances Data)

Toxicity

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

MSDS

• Language:English Provider:Anisic aldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

p-Anisaldehyde Usage And Synthesis

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.

Chemical Properties

Colorless or light yellow liquid ; Cured getting cold. The relative density : 1.119-1.123, the refractive index: 1.5710-1.5750; boiling point: 246-248℃; melting point: 1-2.5℃; flash point 100℃above. Dissolved in 2 volumes of 60% ethanol. Mutually dissolvable with oil flavor. Acid value < 6.0 .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.

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 Chemicalbook of Tian Ye.

Uses

p-Anisaldehyde is the main body of floral perfumes for the deployment of Hawthorn. It can also be used for lilac, orchid, sunflower, acacia, shy flower, black locust, magnolia, wallflowers and sweet bean curd and other floral and new treasure, Hong Wei, aldehyde and other non-fragrant flower essences. It can also be used for other heavy woody sandalwood flavor as well as used in soap flavor. Its sweetness is used in the food and to reconcile flavor.
p-Anisaldehyde has a persistent aroma of hawthorn. It is used as the main spice in hawthorn flowers, sunflower, lilac flavor; Lily of the valley as a flavoring agent in flavor; it can also be used as modifier in the sweet-scented osmanthus flavor as well as for daily flavors and food flavor. The product is allowed for the temporary use of edible spices under China GB2760-86 provisions. It is mainly used for mint flavor of preparation of vanilla, incense and spice, apricot, cream, fennel, caramel, cherry, chocolate, walnuts, raspberry, strawberry, etc. The effect is very good when cooperating with the orange essential oil. 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 can be used for the preparation and organic synthesis of perfume.

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.

Description

p-Methoxybenzaldehyde has a characteristic hawthorne odor and a pungent, anise-like flavor. It has a bitter flavor above 30 - 40 ppm. May be prepared by methylation and oxidation of p-cresol and also by oxidation of anethole.

Chemical Properties

p-Methoxybenzaldehyde has a sweet, floral odor and a pungent, anise-like flavor. It has a bitter flavor above 30 to 40 ppm.

Chemical Properties

clear colorless to pale yellowish liquid

Chemical Properties

p-Anisaldehyde occurs in many essential oils, often together with anethole. It is a colorless to slightly yellowish liquid with a sweet, mimosa, hawthorn odor. p-Anisaldehyde can be hydrogenated to anise alcohol and readily oxidizes to anisic acid when exposed to air. Synthetic routes to anisaldehyde start from p-cresyl methyl ether, which is oxidized, for example, by manganese dioxide or by oxygen or peroxy compounds in the presence of transition metal catalysts .
Another industrial process uses electrochemical oxidation in the presence of lower aliphatic alcohols via the corresponding anisaldehyde dialkyl acetal . Anisaldehyde may also be produced by methylation of 4-hydroxybenzaldehyde, which is easily obtained by oxidation of p-cresol or by Vilsmeier formylation of anisol.

Occurrence

Reported found in essential oils and extracts of vanilla, Acacia farmesiana Willd., Magnoila salicifolia Maxim., Erica arborea, Pirus communis, Boswellia serrata, and others; also in anise, fennel and star anise (especially when aged due to the oxidation of anethole), cranberry, black currant, cinnamon and basil.

Uses

4-Methoxybenzaldehyde is widely utilized in the fragrance and flavor industry. It finds application as an important intermediate in the synthesis of other organic compounds, perfumes and pharmaceuticals like antihistamines. It is also used in the preparation of agrochemicals, dyes and plastic additives. A solution of para-anisaldehyde with acid and ethanol is used as stain in thin layer chromatography (TLC), which provides easy identification of different compounds.

Uses

Perfumery and toilet soaps; odor resembles that of coumarin, but the aldehyde must be mixed with other odorous substances to yield an agreeable odor. Also used in organic syntheses.

Uses

p-Anisaldehyde is a flavoring agent that is a colorless or faintly yellow liquid, hawthorn-like odor. It is miscible in alcohol, ether, and most fixed oils, soluble in propylene glycol, insoluble in glycerin, water, and mineral oil. It is obtained by synthesis. It is also termed anise aldehyde and p-methoxybenzaldehyde.

Preparation

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

Definition

ChEBI: P-methoxybenzaldehyde is a member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4. It has a role as an insect repellent, a human urinary metabolite, a plant metabolite and a bacterial metabolite.

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.

Synthesis Reference(s)

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

General Description

p-anisaldehyde is an aromatic aldehyde commonly found in anise seed oil. It shows acaricidal activity and is primarily used, as a lead compound for the development of new agents for the selective control of house dust mites.

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Taste at 5-10 ppm

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

target

Antifection

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.]

p-Anisaldehyde(123-11-5)Related Product Information

• p-Anisidine
• p-Anisic acid
• 3-METHOXYPROPIONIC ACID
• M-PEG5-CHO
• Methoxyacetic acid
• 3-METHOXY-PROPIONALDEHYDE
• 2-methoxyethanethiol
• 4-Methylphenylacetic acid
• 4-Methylbenzenesulfonhydrazide
• Ethyl p-toluenesulfonate
• Diethyl (tosyloxy)methylphosphonate
• 4'-Methoxyacetophenone
• 4-Methoxybenzyl cyanide
• 4-Methoxyphenylacetic acid
• Methoxypropiophenone
• 4-Methoxyphenylboronic acid
• 4-Methoxybenzenesulfonyl chloride
• p-Anisohydrazide