4-Hydroxybenzoic acid

Base Information

• Chemical Name: 4-Hydroxybenzoic acid
• CAS No.: 99-96-7
• Molecular Formula: C7H6O3
• Molecular Weight: 138.123
• Hs Code.: 2918.21 Oral rat LD50: > 10 gm/kg
• European Community (EC) Number: 202-804-9,621-134-1
• NSC Number: 4961
• UNII: JG8Z55Y12H
• DSSTox Substance ID: DTXSID3026647
• Nikkaji Number: J43.201F
• Wikipedia: 4-Hydroxybenzoic_acid
• Wikidata: Q229970
• Pharos Ligand ID: NAAR8F4VRLWP
• Metabolomics Workbench ID: 37280
• ChEMBL ID: CHEMBL441343
• Mol file: 99-96-7.mol

Synonyms:4-hydroxybenzoate;4-hydroxybenzoic acid;4-hydroxybenzoic acid, calcium salt;4-hydroxybenzoic acid, copper(2+)(1:1) salt;4-hydroxybenzoic acid, dilithium salt;4-hydroxybenzoic acid, dipotassium salt;4-hydroxybenzoic acid, disodium salt;4-hydroxybenzoic acid, monopotassium salt;4-hydroxybenzoic acid, monosodium salt;4-hydroxybenzoic acid, monosodium salt, 11C-labeled;p-hydroxybenzoate;para-hydroxybenzoic acid;sodium p-hydroxybenzoate tetrahydrate

Chemical Property of 4-Hydroxybenzoic acid

Chemical Property:

• Appearance/Colour: white to beige crystalline powder
• Vapor Pressure: 4.48E-05mmHg at 25°C
• Melting Point: 213-217 °C(lit.)
• Boiling Point: 336.2 °C at 760 mmHg
• Flash Point: 171.3 °C
• PSA: 57.53000
• Density: 1.46 g/cm³
• LogP: 1.09040
• Water Solubility.: 5 g/L (20℃)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 138.031694049
• Heavy Atom Count: 10
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=CC(=CC=C1C(=O)O)O
• Sources: 4-Hydroxybenzoic acid is found naturally in various food items such as coconut, raspberry, gooseberry, fennel, anise, pulses, and in raw materials used for making wine and olive fruits. It is also present in the effluent of winery industries, olive oil mills, and pulp and paper industries.^[1]
• Categories and Type: 4-Hydroxybenzoic acid belongs to the class of phenolic acids, specifically hydroxybenzoic acids. It contains a phenol and carboxylic acid functional group.
• Uses and Mechanism of Action: In the pharmaceutical and food industries, 4-Hydroxybenzoic acid is used as a preservative, particularly in the form of its esterified forms, such as ethyl 4-hydroxybenzoate and methyl 4-hydroxybenzoate (parabens).^[2]; In the plastics industry, 4-Hydroxybenzoic acid serves as a precursor for the synthesis of liquid crystal polymers (LCPs) used in high-tech applications in the thermoplastic industry.^[1]; In bioremediation, 4-Hydroxybenzoic acid exhibits various biological properties including antioxidant, antibacterial, antifungal, antimutagenic, antisickling, cardioprotective, antidiabetic, and anticancer activities.^[1]
• Production Methods: Chemical synthesis: ; Commercially synthesized using the Kolbe-Schmitt reaction from petroleum-derived phenol under high temperature and pressure conditions.; ; Microbial synthesis: ; Can be produced from renewable feedstocks via microbial fermentation processes, utilizing metabolically engineered microorganisms such as Escherichia coli, Pseudomonas putida, Corynebacterium glutamicum, and Yarrowia lipolytica.
• Analysis Method: The extraction of 4-Hydroxybenzoic acid from aqueous solutions can be achieved using both nontoxic solvents (e.g., sesame oil, canola oil) and conventional solvents (e.g., benzene, toluene, petroleum ether). Parameters such as distribution coefficient (KD), extraction efficiency (E%), partition coefficient (P), and dimerization constant (D) are evaluated to assess the efficiency of extraction methods. Additionally, high-performance liquid chromatography (HPLC) can be used for quantitative analysis of 4-Hydroxybenzoic acid concentrations.
• References: [1] Extractive separation of 4- hydroxybenzoic acid from aqueous solution using nontoxic and conventional solvents; DOI 10.1016/j.cdc.2021.100782; [2] Microbial synthesis of 4-hydroxybenzoic acid from renewable feedstocks; DOI 10.1016/j.fochms.2021.100059

Technology Process of 4-Hydroxybenzoic acid

There total 490 articles about 4-Hydroxybenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 30.0%

methyl 4-methoxybenzoate (121-98-2) → 4-methoxybenzoic acid (100-09-4) + methyl 4-hydroxylbenzoate (99-76-3,156291-94-0) + 4-hydroxy-benzoic acid (99-96-7)

Guidance literature:

With iodine; aluminium; In cyclohexane; at 20 ℃; for 18h;

DOI:10.1016/j.tetlet.2018.03.010

Reference yield: 9.0%

benzoic acid (65-85-0,8013-63-6) → 2,3-Dihydroxybenzoic acid (303-38-8) + 2,5-dihydroxybenzoic acid. (490-79-9) + 3-Carboxyphenol (99-06-9) + 4-hydroxy-benzoic acid (99-96-7)

Guidance literature:

With oxygen; iron(II) sulfate; In water; at 40 ℃; for 3h; Further byproducts given;

Reference yield: 4.0%

benzoic acid (65-85-0,8013-63-6) → 2,3-Dihydroxybenzoic acid (303-38-8) + 2,5-dihydroxybenzoic acid. (490-79-9) + 3-Carboxyphenol (99-06-9) + salicylic acid (69-72-7,25496-36-0,8052-31-1) + 4-hydroxy-benzoic acid (99-96-7)

Guidance literature:

With oxygen; iron(II) sulfate; In water; at 40 ℃; for 3h; Product distribution; pH 6.8 buffer;

upstream raw materials:

tetrachloromethane

4-[(2-hydroxyphenyl)carbonyl]phenol

(E)-2-(hydroxyimino)-1-(4-hydroxyphenyl)propan-1-one

n-butyllithium

Downstream raw materials:

4-((4-methylbenzyl)oxy)benzoic acid

4-hydroxy-benzoic acid-(2-methoxy-phenyl ester)

9-(4-hydroxyphenyl)acridine

3-dimethylaminomethyl-4-hydroxy-benzoic acid

Refernces

• 1、 Kamilov,Nikonov. "". . . Retrieved 1972.
• 2、 Damtoft, Soeren,Franzyk, Henrik,Jensen, Soeren Rosendal. "FONTANESIOSIDE AND 5-HYDROXYSECOLOGANOL FROM FONTANESIA PHILLYREODES". . p. 705 - 712. Retrieved 1994.
• 3、 H?fle, Gerhard,Reinecke, Silke,Laude, Uwe,Spitzner, Dietrich. "Amethystin, the coloring principle of Stentor amethystinus". . p. 1383 - 1389. Retrieved 2014.
• 4、 Wilschke, Juergen,Sprengel, Birgit,Wolff, Christian,Rudolph, Hansjoerg. "A HYDROXYBUTENOLIDE FROM SPHAGNUM SPECIES". . p. 1725 - 1728. Retrieved 1989.
• 5、 Auyeung, Evelyn,Morris, William,Mondloch, Joseph E.,Hupp, Joseph T.,Farha, Omar K.,Mirkin, Chad A.. "Controlling structure and porosity in catalytic nanoparticle superlattices with DNA". . p. 1658 - 1662. Retrieved 2015.
• 6、 Zhou,Pan,Wu,Qian,He,Chen. "Efficient catalytic oxidation of alcohol to carbonyl compounds over CoFe hydrotalcites". . p. 84106 - 84112. Retrieved 2016.
• 7、 Bell, Stephen G.,McMillan, James H. C.,Yorke, Jake A.,Kavanagh, Emma,Johnson, Eachan O. D.,Wong, Luet-Lok. "Tailoring an alien ferredoxin to support native-like P450 monooxygenase activity". . p. 11692 - 11694. Retrieved 2012.
• 8、 Zhang, Yongji,Zhang, Yiqing,Zhou, Lingling,Tan, Chaoqun. "Inactivation of bacillus subtilis spores using various combinations of ultraviolet treatment with addition of hydrogen peroxide". . p. 609 - 614. Retrieved 2014.
• 9、 Jackson, D. Y.,Jacobs, J. W.,Sugasawara, R.,Reich, S. H.,Bartlett, P. A.,Schultz, P. G.. "An Antibody-Catalyzed Claisen Rearrangement". . p. 4841 - 4842. Retrieved 1988.
• 10、 Ma, Minhui,Lee, Tony,Kwong, Elizabeth. "Interaction of Methylparaben Preservative with Selected Sugars and Sugar Alcohols". . p. 1715 - 1723. Retrieved 2002.