Basic information Product description Chemical Properties odor Uses Content Analysis Toxicity FEMA limits Production method Safety Related Supplier
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)
- refractive index n
- FEMA 2670 | P-METHOXYBENZALDEHYDE
- Flash point:228 °F
- storage temp. Refrigerator
- solubility 2g/l
- form Liquid
- color Clear colorless to yellow
- Odorsweetish odor
- PH7 (2g/l, H2O, 20℃)
- explosive limit1.4-5.3%(V)
- Water Solubility Miscible with acetone, alcohol, ether, chloroform and benzene. Immiscible with water.
- Sensitive Air Sensitive
- Decomposition > 160°C
- JECFA Number878
- Merck 14,663
- BRN 471382
- CAS DataBase Reference123-11-5(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzaldehyde, 4-methoxy-(123-11-5)
- EPA Substance Registry SystemBenzaldehyde, 4-methoxy- (123-11-5)
- 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
- RIDADR UN 3316 9/PG 2
- WGK Germany 1
- RTECS BZ2625000
- F 10-23
- Autoignition Temperature220 °C
- TSCA Yes
- HazardClass IRRITANT
- PackingGroup II
- HS Code 29124900
- Hazardous Substances Data123-11-5(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 1510 mg/kg (Jenner)
p-Anisaldehyde Usage And Synthesis
- Product descriptionAnisaldehyde(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 PropertiesColorless 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.
- odorThere 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.
- Usesp-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 Analysis0.8g 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.
- ToxicityADI 1mg/kg(CE). LD50 1510 mg/kg(Rat, Oral). No evident abnormal showed in the process of growth, blood, tissues from rats which were either raised by feeds containing 1000 mg/kg anise aldehyde for 27～28 weeks or raised by feeds containing 10000 mg/kg anise aldehyde for 15 weeks.
- FEMA limitsFEMA (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 methodIt 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.
- Descriptionp-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 Propertiesp-Methoxybenzaldehyde has a sweet, floral odor and a pungent, anise-like flavor. It has a bitter flavor above 30 to 40 ppm.
- Chemical Propertiesclear colorless to pale yellowish liquid
- Chemical Propertiesp-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.
- OccurrenceReported 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.
- UsesPerfumery 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.
- Usesp-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.
- PreparationBy methylation and oxidation of p-cresol and also by oxidation of anethole.
- Aroma threshold valuesAroma characteristics at 1.0%: sweet powdery, spicy creamy, fruity, vanilla and hay-like. Coumarin, almond, anisic with berry nuances.
- Taste threshold valuesTaste 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
- Safety ProfileModerately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes
- MetabolismAnisic 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 MethodsWash 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 Preparation Products And Raw materials
- Preparation Productscis-Anethol3,5-DIMETHOXYPHENYLACETIC ACIDFLUCYTHRINATED(-)-4-HydroxyphenylglycineDL-4-HYDROXYPHENYLGLYCINE5-(4-METHOXYPHENYL)HYDATOINN-(4-Methoxybenzyl)-N-methylamine4-Methoxybenzyl alcoholAmino-4-methoxyben-zeneacetic acidOctyl 4-methoxycinnamate
- Raw materialsSodium bisulfiteManganese dioxideHexamethylenetetramineSodium dichromate dihydratePotassium dichromateAnisoleSulfanilic acidp-Hydroxybenzaldehydep-CresolMesitylenecis-AnetholOzoneTetrapotassium hexacyanoferrate trihydrateCOREOPSISYELLOWEXTRACT4-MethylanisolePEANUT OILGALANGAL ROOT OILDill Oil
- 3,5-Dimethoxybenzaldehyde p-Hydroxybenzaldehyde 2,5-Dimethoxybenzaldehyde Cuminaldehyde 3-ANISALDEHYDE Anise oil 2,4-Dimethoxybenzaldehyde 3-(4-ISOPROPYLPHENYL)ISOBUTYRALDEHYDE Anisic acid 2,3-Dimethoxybenzaldehyde 2-ANISALDEHYDE Veratraldehyde 1-Nonanal 4-(Trifluoromethoxy)aniline 4-Methoxybenzylchloride Paraldehyde p-Anisaldehyde 4-Methoxyphenol
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