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4-Methoxybenzoic acid

CAS No.
100-09-4
Chemical Name:
4-Methoxybenzoic acid
Synonyms
4-Methoxybenzoic acid;ANISIC ACID;4-ANISIC ACID;P-METHOXYBENZOIC ACID;Anisic;4-METHOXYBENZOIC AICD;para-anisic acid;4-Methoxybenzoic;benzoicacid,4-methoxy-;p Acid
CBNumber:
CB6746524
Molecular Formula:
C8H8O3
Molecular Weight:
152.15
MDL Number:
MFCD00002542
MOL File:
100-09-4.mol
MSDS File:
SDS
Last updated:2024-03-12 17:20:04

4-Methoxybenzoic acid 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
Flash point 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
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
Substances Added to Food (formerly EAFUS) 4-METHOXYBENZOIC ACID
CAS DataBase Reference 100-09-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 4SB6Y7DMM3
NIST Chemistry Reference Benzoic acid, 4-methoxy-(100-09-4)
EPA Substance Registry System Benzoic acid, 4-methoxy- (100-09-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P305+P351+P338-P301+P312+P330
Hazard Codes  Xi,Xn
Risk Statements  36/37/38-22
Safety Statements  26-36-24/25
WGK Germany  1
RTECS  BZ4395000
Autoignition Temperature 185 °C
Hazard Note  Irritant
TSCA  Yes
HS Code  29189090
Toxicity LD50 orally in Rabbit: > 5000 mg/kg
NFPA 704
0
2 0

4-Methoxybenzoic acid price More Price(50)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.05971 4-Methoxybenzoic acid for synthesis 100-09-4 250g $125 2024-03-01 Buy
Sigma-Aldrich 8.05971 4-Methoxybenzoic acid for synthesis 100-09-4 1kg $225 2024-03-01 Buy
Sigma-Aldrich 117390 4-Methoxybenzoic acid ReagentPlus , 99% 100-09-4 5g $16.6 2024-03-01 Buy
Sigma-Aldrich 117390 4-Methoxybenzoic acid ReagentPlus , 99% 100-09-4 100g $47.5 2024-03-01 Buy
Sigma-Aldrich W394512 p-Anisic acid natural, 99%, FG 100-09-4 10Kg $2250 2023-01-07 Buy
Product number Packaging Price Buy
8.05971 250g $125 Buy
8.05971 1kg $225 Buy
117390 5g $16.6 Buy
117390 100g $47.5 Buy
W394512 10Kg $2250 Buy

4-Methoxybenzoic acid Chemical Properties,Uses,Production

Description

P-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 Properties

It 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.

Uses

4-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.

Preparation

To 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.

Definition

ChEBI: 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 Description

4-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 Profile

4-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

Hazard

Thermal decomposition can lead to release of irritating gases and vapors, Carbon monoxide (CO), Carbon dioxide (CO2).

Biochem/physiol Actions

The 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 Profile

Poison by subcutaneous route.When heated to decomposition it emits acrid smoke andirritating vapors.

Purification Methods

Crystallise 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.

123-11-5
100-09-4
Synthesis of 4-Methoxybenzoic acid from p-Anisaldehyde
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View Lastest Price from 4-Methoxybenzoic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
p-Anisic acid pictures 2024-03-19 p-Anisic acid
100-09-4
US $5.00-1.00 / kg 1kg 99% 600tons Hebei Dangtong Import and export Co LTD
4-Methoxybenzoic acid pictures 2024-03-19 4-Methoxybenzoic acid
100-09-4
US $2.00 / KG 1KG ≥99.5% 500mt/year Jinan Finer Chemical Co., Ltd
p-Anisic acid pictures 2024-03-18 p-Anisic acid
100-09-4
US $0.00 / kg 1kg 0.99 10T Shandong Hanjiang Chemical Co., Ltd
  • p-Anisic acid pictures
  • p-Anisic acid
    100-09-4
  • US $5.00-1.00 / kg
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  • Hebei Dangtong Import and export Co LTD
  • p-Anisic acid pictures
  • p-Anisic acid
    100-09-4
  • US $0.00 / kg
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  • Shandong Hanjiang Chemical Co., Ltd
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