ChemicalBook > CAS DataBase List > 4-Methoxybenzoic acid

4-Methoxybenzoic acid

Product Name
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
Formula Weight
152.15
MOL File
100-09-4.mol
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4-Methoxybenzoic acid Property

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
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
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
Benzoic acid, 4-methoxy-(100-09-4)
EPA Substance Registry System
Benzoic acid, 4-methoxy- (100-09-4)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.05971
Product name
4-Methoxybenzoic acid
Purity
for synthesis
Packaging
250g
Price
$125
Updated
2024/03/01
Sigma-Aldrich
Product number
8.05971
Product name
4-Methoxybenzoic acid
Purity
for synthesis
Packaging
1kg
Price
$225
Updated
2024/03/01
Sigma-Aldrich
Product number
117390
Product name
4-Methoxybenzoic acid
Purity
ReagentPlus , 99%
Packaging
5g
Price
$16.6
Updated
2024/03/01
Sigma-Aldrich
Product number
117390
Product name
4-Methoxybenzoic acid
Purity
ReagentPlus , 99%
Packaging
100g
Price
$47.5
Updated
2024/03/01
Sigma-Aldrich
Product number
W394512
Product name
p-Anisic acid
Purity
natural, 99%, FG
Packaging
10Kg
Price
$2250
Updated
2023/01/07
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4-Methoxybenzoic acid Chemical Properties,Usage,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].

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.

Solubility in organics

Soluble in alcohol and oils.

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.

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View Lastest Price from 4-Methoxybenzoic acid manufacturers

Dorne Chemical Technology co. LTD
Product
Anisic acid 100-09-4
Price
US $1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10 ton
Release date
2024-03-26
CONTIDE BIOTECH CO.,LTD
Product
p-Anisic acid 100-09-4
Price
US $0.00/G
Min. Order
1G
Purity
99%
Supply Ability
20
Release date
2024-03-27
Hebei Mujin Biotechnology Co.,Ltd
Product
p-Anisic acid 100-09-4
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
99%
Supply Ability
1000000kg/month
Release date
2021-03-11

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