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P-Anisic acid, also known as 4-Methoxybenzoic acid or draconic acid, is an organic acid that has a sweet flavor.
P-Anisic acid is one of the isomers of anisic acid, including m-anisic acid and o-anisic acid.
The term "anisic acid" often refers to this form specifically.
CAS: 100-09-4
MF: C8H8O3
MW: 152.15
EINECS: 202-818-5
Synonyms
PARA-METHOXYBENZOICACID;p-Anissure;4-methoxy-benzoicaci;Anisic acid, para;benzoicacid,4-methoxy-;Draconic acid;draconicacid;Kyselina 4-methoxybenzoova
p-Anisic Acid is produced through the oxidation of p-cresyl-methyl ether.
p-Anisic Acid is a methoxybenzoic acid substituted with a methoxy group at position C-4.
p-Anisic Acid has a role as a plant metabolite.
p-Anisic Acid is functionally related to a benzoic acid.
p-Anisic Acid is a conjugate acid of a 4-methoxybenzoate.
p-Anisic Acid is the sole source of carbon and energy for growth in the cultures of Nocardia sp. DSM 1069.
p-Anisic Acid is effective in clearing congestion in the lungs and the respiratory tracts in conditions like asthma or bronchitis.
p-Anisic Acid, also known as 4-methoxybenzoic acid or draconic acid, is one of the isomers of anisic acid.
The term "anisic acid" often refers to this form specifically.
p-Anisic Acid is a white crystalline solid which is insoluble in water, highly soluble in alcohols, and soluble in ether and ethyl acetate.
P-Anisic Acid, also known as 4-methoxybenzoic acid, is a compound found in anise, vanilla, and other plants.
Widely used in cosmetics as a preservative and fragrance ingredient, p-Anisic Acid inhibits microbial growth, extending the shelf life of skincare and haircare products.
This crystalline white powder appears as tiny, odorless crystals, with a chemical formula C8H8O3.
p-Anisic Acid's antimicrobial properties help prevent bacterial and fungal contamination in cosmetics, ensuring product safety and longevity.
P-Anisic Acid is valued for its ability to maintain product quality and freshness, making it a vital component in various cosmetic formulations.
p-anisic acid is derived from the anise plant.
p-Anisic Acid has antibacterial properties which make it a good preservative and is commonly used in place of parabens or synthetic preservatives.
p-Anisic Acid is also used in formulations as a mild fragrance.
p-Anisic Acid is an orally available tyrosinase inhibitor that has antioxidant, anti-anxiety, anti-inflammatory, anti-tumor, anti-diabetic, and preservative properties.
p-Anisic Acid can be used as a preservative in the cosmetics field.
p-Anisic Acid Chemical Properties
Melting point: 182-185 °C(lit.)
Boiling point: 275 °C
Density: 1.385
Bulk density: 380kg/m3
Vapor pressure: 0.001Pa at 25℃
Refractive index: 1.571-1.576
FEMA: 3945 | 4-METHOXYBENZOIC ACID
Fp: 185 °C
Storage temp.: Store below +30°C.
Solubility H2O: soluble2500 parts
Form: Powder
Pka: 4.50(at 25℃)
Color: White to slightly gray-beige
PH: 3-4 (0.3g/l, H2O, 20℃)
Odor: at 10.00 % in dipropylene glycol. faint putrid sweet cadaverous
Odor Type: animal
Biological source: synthetic
Water Solubility: Soluble in water at 20°C 0.3g/L. Soluble in alcohol, ethyl acetate and ether.
Merck: 14,666
JECFA Number: 883
BRN: 508910
Stability: Stable. Incompatible with strong oxidizing agents.
InChIKey: ZEYHEAKUIGZSGI-UHFFFAOYSA-N
LogP: 1.96
CAS DataBase Reference: 100-09-4(CAS DataBase Reference)
NIST Chemistry Reference: p-Anisic Acid (100-09-4)
EPA Substance Registry System: p-Anisic Acid (100-09-4)
p-Anisic Acid appears as a colorless needle crystal at room temperature.
p-Anisic Acid is soluble in ethanol, ether, and chloroform, and only slightly soluble in hot water.
p-Anisic Acid remains insoluble in cold water.
p-Anisic Acid is used as an intermediate for aniracetam, as well as a preservative and fragrance.
Uses
p-Anisic Acid is used in oxidation and reduction of cytochrome c in solution through different self-assembled monolayers on gold electrodes using cyclic voltammetry.
p-Anisic acid has antiseptic properties.
p-Anisic Acid is also used as an intermediate in the preparation of more complex organic compounds.
p-Anisic acid has antiseptic properties.
p-Anisic Acid is also used as an intermediate in the preparation of more complex organic compounds.
Preparation
To obtain p-Anisic Acid, the mole ratio of cobalt and manganese is modified and p-methoxy toluene is reacted with oxygen or an oxygen-containing gas in the presence of acetic acid.
The following is the experimental procedure:
1. Using n-hexyl bromide, tri (n-hexyl) amine, para-methoxy toluene with cobalt chloride hexahydrate in about 9h;
2. By a catalytic oxidation process using p-methoxy toluene and propionic acid over a catalyst comprising of CoBr2.6H2O and MnBr2.4H2O with a reaction time of 20h;
3. Through changing the mole ratio of cobalt and manganese, using p-methoxy toluene with oxygen or oxygen containing gas in the presence of acetic acid to obtain the product.
Synthesis and occurrence
p-Anisic acid is found naturally in anise.
p-Anisic Acid was first synthesized in 1841 by Auguste Cahours by oxidizing anethole that he had isolated from anise by recrystallization with diluted nitric acid:
CH3CH=CHC6H4OCH3 + HNO3 → CH3OC6H4CHO + others
CH3OC6H4CHO + HNO3 → CH3OC6H4COOH + others
Oxidation of anisaldehyde, which was Cahours' intermediate product, is still used nowadays.
Anisic acid can also be obtained synthetically by the oxidation of p-methoxyacetophenone.
Reactivity Profile
p-Anisic Acid belongs to Aromatic acid hydrazides (Others include isonicotinic, benzoic, and salicylic).
The reaction of thiosemicarbazide and aromatic acid hydrazides with 4H-chromen-4-imines could prepare o-hydroxyphenyl derivatives of 1H-pyrazolethioamides and 1H-pyrazol-5-ylphenols derivatives.
Biochem/physiol Actions
The cytochrome P450 enzyme CYP199A4, a heme-dependent cytochrome P450 (CYP) monooxygenase enzyme, can efficiently demethylate p-Anisic Acid.
Mechanistically, O-demethylation of p-Anisic Acid occurs via hydrogen abstraction by Compound I, followed by oxygen rebound to give the hydroxylated hemiacetal which spontaneously decomposes to yield p-Anisic Acid and formaldehyde.
