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4-Methoxybenzoic acid

P-anisic acid, known also as 4-methoxybenzoic acid or draconic acid, is an organic acid with sweet flavor. It is one of the isomers (m-anisic acid, and o-anisic acid) of anisic acid. The term anisic acid is often used to describe p-anisic acid. P-anisic acid is produced through the oxidation of p-cresyl-methyl ether.
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CAS:100-09-4
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4-Methoxybenzoic acid Basic information
Product Name:4-Methoxybenzoic acid
Synonyms:p-Anisic acid (4-Methoxybenzoic acid);P-anisic acid crystalline;p-Methoxy benzoic acid (p-Anisic acid);P-ANISIC ACID 99+%;P-AnisicAcidForSynthesis;4-AnisicAcid98%;4-Methoxybenzoic acid, 98+%;4-Anisic Acid 98%
CAS:100-09-4
MF:C8H8O3
MW:152.15
EINECS:202-818-5
Product Categories:carboxylic acid;Organic acids;Absolute Configuration Determination (Exciton Chirality CD Method);Enantiomer Excess & Absolute Configuration Determination;Exciton Chirality CD Method (for Hydroxyl Groups);Analytical Chemistry;Benzoic Acids (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;acid;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Liquid Crystal intermediates;Pyridines;p-Anisic acid;100-09-4
Mol File:100-09-4.mol
4-Methoxybenzoic acid Structure
4-Methoxybenzoic acid Chemical Properties
Melting point 182-185 °C(lit.)
Boiling point 275 °C
density 1.385
vapor pressure 0.001Pa at 25℃
FEMA 3945 | 4-METHOXYBENZOIC ACID
refractive index 1.571-1.576
Fp 185 °C
storage temp. Store below +30°C.
solubility H2O: soluble2500 parts
form Powder
pka4.50(at 25℃)
color White to slightly gray-beige
PH3-4 (0.3g/l, H2O, 20℃)
Odorat 10.00 % in dipropylene glycol. faint putrid sweet cadaverous
Odor Typeanimal
Water Solubility Soluble in water at 20°C 0.3g/L. Soluble in alcohol, ethyl acetate and ether.
Merck 14,666
JECFA Number883
BRN 508910
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyZEYHEAKUIGZSGI-UHFFFAOYSA-N
LogP1.96
CAS DataBase Reference100-09-4(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, 4-methoxy-(100-09-4)
EPA Substance Registry SystemBenzoic acid, 4-methoxy- (100-09-4)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-22
Safety Statements 26-36-24/25
WGK Germany 1
RTECS BZ4395000
Autoignition Temperature185 °C
Hazard Note Irritant
TSCA Yes
HS Code 29189090
ToxicityLD50 orally in Rabbit: > 5000 mg/kg
MSDS Information
ProviderLanguage
4-Methoxybenzoic acid English
SigmaAldrich English
ACROS English
ALFA English
4-Methoxybenzoic acid Usage And Synthesis
DescriptionP-Anisic acid, also known as 4-Methoxybenzoic acid or draconic acid, is an organic acid that has a sweet flavor. It 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. P-anisic acid is produced through the oxidation of p-cresyl-methyl ether.
Chemical PropertiesIt appears as a colorless needle crystal at room temperature. It is soluble in ethanol, ether, and chloroform, and only slightly soluble in hot water. It remains insoluble in cold water. It is used as an intermediate for aniracetam, as well as a preservative and fragrance.
Uses4-Methoxybenzoic acid (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. It is also used as an intermediate in the preparation of more complex organic compounds.
PreparationTo obtain 4-Methoxybenzoic 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.
DefinitionChEBI: 4-methoxybenzoic acid is a methoxybenzoic acid substituted with a methoxy group at position C-4. It has a role as a plant metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 4-methoxybenzoate.
Synthesis Reference(s)Journal of Heterocyclic Chemistry, 25, p. 973, 1988 DOI: 10.1002/jhet.5570250351
Tetrahedron Letters, 34, p. 4603, 1993 DOI: 10.1016/S0040-4039(00)60635-4
General Description4-Methoxybenzoic acid is the sole source of carbon and energy for growth in the cultures of Nocardia sp. DSM 1069. It is effective in clearing congestion in the lungs and the respiratory tracts in conditions like asthma or bronchitis.
Reactivity Profile4-Methoxybenzoic 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[4].
4-Methoxybenzoic acid
HazardThermal decomposition can lead to release of irritating gases and vapors, Carbon monoxide (CO), Carbon dioxide (CO2).
Biochem/physiol ActionsThe cytochrome P450 enzyme CYP199A4, a heme-dependent cytochrome P450 (CYP) monooxygenase enzyme, can efficiently demethylate 4-methoxybenzoic acid. Mechanistically, O-demethylation of 4-methoxybenzoic acid occurs via hydrogen abstraction by Compound I, followed by oxygen rebound to give the hydroxylated hemiacetal which spontaneously decomposes to yield 4-hydroxybenzoic acid and formaldehyde[5].
Safety ProfilePoison by subcutaneous route.When heated to decomposition it emits acrid smoke andirritating vapors.
Purification MethodsCrystallise p-anisic acid from EtOH, water, EtOH/water or toluene. The S-benzylisothiuronium salt has m 189o (from EtOH). [Beilstein 10 II 91, 10 III 280, 10 IV 346.]
References[1] Michael Ash (2004) Handbook of Preservatives
[2] Asim Kumar Mukhopadhyay (2004) Industrial Chemical Cresols and Downstream Derivatives
[3] https://en.wikipedia.org/wiki/P-Anisic_acid
[4] Zahorulko S, et al. Recyclization of 4 H -chromen-4-imine derivatives under the influence of dinucleophiles with the formation of functionally substituted pyrazoles. Monatshefte für Chemie - Chemical Monthly, 2019; 150: 1487–1493.
[5] Coleman T, et al. The importance of the benzoic acid carboxylate moiety for substrate recognition by CYP199A4 from Rhodopseudomonas palustris HaA2. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, 2016; 1864: 667-675.
Tag:4-Methoxybenzoic acid(100-09-4) Related Product Information
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