p-Anisaldehyde
- Iupac Name：4-methoxybenzaldehyde
- CAS No.: 123-11-5
- Molecular Weight：136.14792
- Modify Date.: 2022-11-16 18:41
- Introduction:
p-Anisaldehyde, with the chemical formula C8H8O2 and CAS registry number 123-11-5, is a compound known for its aromatic and aldehyde properties. This colorless to pale yellow liquid, also referred to as 4-Methoxybenzaldehyde, is characterized by its methoxy group attached to the benzene ring. It is commonly used in the fragrance and flavor industry, as well as in the synthesis of pharmaceuticals and organic compounds. p-Anisaldehyde has a sweet, floral, and slightly spicy odor, reminiscent of anise or licorice. It is an important compound in the field of organic chemistry and perfumery, contributing to the creation of various scents and flavors.
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1. Names and Identifiers
- 1.1 Name
- p-Anisaldehyde
- 1.2 Synonyms
4-Methoxybenzald 4-Methoxybenzaldehyde 4-methoxy-benzaldehyde AKOS BBS-00003185 Anisal Anisaldehyd ANISALDEHYDE Anisaldehyde solution ANISALDEHYDE extrapure Anisaldehyde test solution(ChP) EINECS 204-602-6 FEMA 2670 LABOTEST-BB LT00920037 MFCD00003385 Natural p-Anisaldehyde Obepin p-Anisaldehyde,contains Acetic Acid,H2SO4) Ethanol Анисовый альдегид, Кратежин, 4-Methoxybenzaldehyde, p-Anisaldehyde, Anisic aldehyde, Anisaldehyde
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- 1.3 CAS No.
- 123-11-5
- 1.4 CID
- 31244
- 1.5 EINECS(EC#)
- 204-602-6
- 1.6 Molecular Formula
- C8H8O2 (isomer)
- 1.7 Inchi
- InChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
- 1.8 InChIkey
- ZRSNZINYAWTAHE-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- COC1=CC=C(C=C1)C=O
- 1.10 Isomers Smiles
- COC1=CC=C(C=C1)C=O
2. Properties
- 2.1 Density
- 1.121
- 2.1 Melting point
- -1℃
- 2.1 Boiling point
- 248-249℃
- 2.1 Refractive index
- 1.571-1.574
- 2.1 Flash Point
- 116℃
- 2.2 Precise Quality
- 136.05200
- 2.2 PSA
- 26.30000
- 2.2 logP
- 1.50770
- 2.2 Solubility
- 2g/l
- 2.3 Viscosity
- Dynamic viscosity = 4.22 mPa s at 25 °C 2017
- 2.4 VaporDensity
- 4.7 (Air = 1)
- 2.5 Appearance
- White powder
- 2.6 Storage
- Air Sensitive. Light Sensitive. Ambient temperatures.
- 2.7 Color/Form
- Oil
- 2.8 Decomposition
- Hazardous decomposition products formed under fire conditions: Carbon oxides
- 2.9 Odor
- Hawthorn odor
- 2.10 PH
- 7 (2g/l, H2O, 20℃)
- 2.11 pKa
- pKa 15.96 (25 °,hydrate, 1% EtOH)
- 2.12 Water Solubility
- Insoluble (soluble in alcohol, ether)
- 2.13 Spectral Properties
- INDEX OF REFRACTION: 1.5730 @ 20 DEG C/D; MAX ABSORPTION (HEXANE): 272 NM (LOG E= 4.20); 278 NM (LOG E= 4.10); 286 NM (LOG E= 3.74); SADTLER REFERENCE NUMBER: 1946 (IR, PRISM); 10848 (IR, GRATING); 126 (NMR)
IR: 1081 (Coblentz Society Spectral Collection)
UV: 536 (Sadtler Research Laboratories Spectral Collection)
NMR: 194 (Varian Associates NMR Spectra Catalogue)
MASS: 694 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
- 2.14 Stability
- Stable under normal temperatures and pressures. Volatile in steam.
- 2.15 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 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 Preparation Products And Raw materials Preparation Products
- 3.2 Usage
- 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.
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4. Safety and Handling
- 4.1 Hazard Codes
- Xn
- 4.1 Risk Statements
- R22
- 4.1 Safety Statements
- 26-45-36/37-16-7
- 4.1 Packing Group
- I; II; III
- 4.1 Hazard Class
- IRRITANT
- 4.1 RIDADR
- 225kgs
- 4.1 Safety Profile
- Moderately toxic byingestion. A skin irritant. Mutation datareported. Combustible liquid. When heatedto decomposition it emits acrid smoke andirritating fumes
- 4.2 Formulations/Preparations
- GRADES: LIQ & CRYSTALS, LATTER BEING THE DISULFITE COMPD.
- 4.3 WGK Germany
- 1
- 4.3 RTECS
- BZ2625000
- 4.3 Report
-
Reported in EPA TSCA Inventory.
- 4.4 Safety
-
Hazard Codes:?
Xn,
Xi,
T,
F
Risk Statements: 22-36/37/38-39-23/24/25-11?
R22: Harmful if swallowed.?
R36/37/38: Irritating to eyes, respiratory system and skin.?
R39: Danger of very serious irreversible effects.?
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.?
R11: Highly flammable.
Safety Statements: 26-45-36/37-16-7?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37: Wear suitable protective clothing and gloves.?
S16: Keep away from sources of ignition.?
S7: Keep container tightly closed.
RIDADR: UN 3316 9/PG 2
WGK Germany: 1
RTECS: BZ2625000
F: 10-23
HazardClass: IRRITANT
HS Code: 29124900
Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
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- 4.5 Sensitive
- Air Sensitive
- 4.6 Specification
-
Precautions: Do not ingest. Do not breathe gas/fumes/vapor/spray.?Keep away from heat. Keep away from sources of ignition. Avoid contact with skin and eyes. Empty containers pose a fire risk, evaporate the residue under a fume hood. Ground all equipment containing material. Wear suitable protective clothing. In case of insufficient ventilation, wear suitable respiratory equipment. If ingested, seek medical advice immediately and show the container or the label.
Storage: Keep container in a cool, well-ventilated area. Keep container tightly closed.
- 4.7 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| guinea pig |
LD50 |
oral |
1260mg/kg (1260mg/kg) |
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) |
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
| mouse |
LD50 |
oral |
1859mg/kg (1859mg/kg) |
GASTROINTESTINAL: NECROTIC GHANGES
GASTROINTESTINAL: OTHER CHANGES
LIVER: FATTY LIVER DEGERATION |
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 58(8), Pg. 20, 1993. |
| rabbit |
LD50 |
skin |
> 5gm/kg (5000mg/kg) |
? |
Food and Cosmetics Toxicology. Vol. 12, Pg. 823, 1974. |
| rat |
LD50 |
oral |
1510mg/kg (1510mg/kg) |
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) |
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
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5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
123-11-5Total: 319 Synthesis Route
8. Other Information
- 8.0 Usage
- 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.
- 8.1 Merck
- 14,663
- 8.2 BRN
- 471382
- 8.3 毒性
- LD50 orally in rats: 1510 mg/kg (Jenner)
- 8.4 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.
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- 8.5 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.
- 8.6 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.
- 8.7 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. - View all
- 8.8 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.
- 8.9 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.
- 8.10 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. - View all
- 8.11 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.
- 8.12 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.
- 8.13 Chemical Properties
- clear colorless to pale yellowish liquid
- 8.14 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.
- 8.15 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.
- 8.16 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.
- 8.17 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.
- 8.18 Preparation
- By methylation and oxidation of p-cresol and also by oxidation of anethole.
- 8.19 Aroma threshold values
- Aroma characteristics at 1.0%: sweet powdery, spicy creamy, fruity, vanilla and hay-like. Coumarin, almond, anisic with berry nuances.
- 8.20 Taste threshold values
- Taste characteristics at 5 to 10 ppm: sweet powdery, vanilla creamy, spice anise, nutty, cherry pit and almond-like nuances.
- 8.21 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
- 8.22 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.
- 8.23 Flammability and Explosibility
- Nonflammable
- 8.24 Biochem/physiol Actions
- Taste at 5-10 ppm
- 8.25 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
- 8.26 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).
- 8.27 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.]
9. Computational chemical data
- Molecular Weight: 136.14792g/mol
- Molecular Formula: C8H8O2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 136.052429494
- Monoisotopic Mass: 136.052429494
- Complexity: 104
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 26.3
- Heavy Atom Count: 10
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAAAAAADASgmAIyBoAABACIAihSgAACCAAkIAAIiAEGCMgMJjKENRqAMSAkwBEIqYeIzADOIAAAAAAAAABAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
-
Introduction p-Anisaldehyde, also known scientifically as 4-methoxybenzaldehyde, is a versatile compound in organic chemistry with various applications. Known for its anise-like fragrance, this aromat..
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p-Anisaldehyde, an important fine chemical, is widely used in fragrances due to its long-lasting hawthorn scent. It is also an intermediate for the production of drugs such as hydroxylamine penicillin..
-
Background technology p-Anisaldehyde, also known as anisaldehyde, is a colorless or light yellow liquid with a long-lasting hawthorn flower aroma. It is an important synthetic fragrance and can also b..
-
Fragrance enhancers have gained attention in the market for their excellent scenting properties. However, due to different compositions, their applications vary greatly. p-Anisaldehyde, a substance wi..
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