4-Hydroxybenzaldehyde

Base Information

• Chemical Name: 4-Hydroxybenzaldehyde
• CAS No.: 123-08-0
• Deprecated CAS: 1187488-60-3
• Molecular Formula: C7H6O2
• Molecular Weight: 122.123
• Hs Code.: 2912.49
• European Community (EC) Number: 204-599-1,803-229-1
• NSC Number: 2127
• UNII: O1738X3Y38
• DSSTox Substance ID: DTXSID8059552
• Nikkaji Number: J1.156.979J,J43.312H
• Wikipedia: 4-Hydroxybenzaldehyde
• Wikidata: Q1953888
• Metabolomics Workbench ID: 41494
• ChEMBL ID: CHEMBL14193
• Mol file: 123-08-0.mol

Synonyms:4-hydroxybenzaldehyde;p-formylphenol;p-hydroxybenzaldehyde;para-hydroxybenzaldehyde

Chemical Property of 4-Hydroxybenzaldehyde

Chemical Property:

• Appearance/Colour: yellow to light brown crystalline powder
• Vapor Pressure: 0.0171mmHg at 25°C
• Melting Point: 112-116°C(lit.)
• Refractive Index: 1.618
• Boiling Point: 246.6 °C at 760 mmHg
• Flash Point: 101.3 °C
• PSA: 37.30000
• Density: 1.226 g/cm³
• LogP: 1.20470
• Water Solubility.: 13 g/L (30℃)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 122.036779430
• Heavy Atom Count: 9
• Complexity: 93.1

Purity/Quality:

99.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzaldehydes
• Canonical SMILES: C1=CC(=CC=C1C=O)O
• Chemical Composition and Structure: 4-Hydroxybenzaldehyde (4-HBA) is an organic compound belonging to the class of hydroxybenzaldehydes. It is characterized by a benzene ring with a hydroxyl group (-OH) and an aldehyde group (-CHO) attached at the para position.
• Sources: 4-Hydroxybenzaldehyde is found naturally in plants such as Gastrodia elata (Tianma) and Vanilla planifolia (vanilla orchid). It can also be synthesized chemically.
• Uses: In medicine, 4-HBA has been studied for its potential to improve insulin resistance, inhibit cholinesterase, and exhibit antiepileptic and anticonvulsive activities. It may also have applications as an antiepileptic and anticonvulsant agent.; In the cosmetic industry, derivatives of 4-HBA are explored as tyrosinase inhibitors, which help prevent excessive pigmentation.; In the food industry, 4-HBA and its derivatives are used as flavoring agents. For example, 4-hydroxybenzaldehyde is one of the compounds contributing to the flavor of natural vanilla.; Studies have demonstrated the synergistic effects of 4-hydroxybenzaldehyde with certain antibiotics, suggesting its potential role in modulating bacterial metabolism and antibiotic susceptibility.
• Mechanism of Action: 4-Hydroxybenzaldehyde has been studied for its various biological activities, including its ability to inhibit GABA transaminase, modulate bacterial metabolism, and act as a flavoring agent. Its mechanism of action involves interactions with specific molecular targets, such as enzymes and receptors.

Technology Process of 4-Hydroxybenzaldehyde

There total 362 articles about 4-Hydroxybenzaldehyde 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: 99.0%

(4-hydroxyphenyl)methanol (623-05-2) + benzyl alcohol (100-51-6,185532-71-2) → benzaldehyde (100-52-7) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1)

Guidance literature:

With air; potassium carbonate; at 20 ℃; for 12h;

DOI:10.1002/adsc.200900405

Reference yield: 72.0%

1-butylpyridinium bromide (874-80-6) + 4-methoxy-benzaldehyde (123-11-5) → 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + p-butoxybenzaldehyde (5736-88-9)

Guidance literature:

at 100 ℃; Microwave irradiation; Neat (no solvent);

DOI:10.2174/157017811794557741

Reference yield: 55.6%

para-xylene (106-42-3) → 4-methyl-benzaldehyde (104-87-0) + terephthalaldehyde, (623-27-8) + benzaldehyde (100-52-7) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1)

Guidance literature:

With oxygen; WO(x); α -alumina; mixture of; at 560 ℃; Product distribution / selectivity; Gas phase;

upstream raw materials:

formaldehyd

sodium phenoxide

formic acid

4-acetoxybenzoyl chloride

Downstream raw materials:

4-hydroxy-3-(piperidin-1-ylmethyl)benzaldehyde

2-(4-hydroxyphenyl)-2-(piperidin-1-yl)acetonitrile

4-(4-hydroxy-benzylidene)-2-thioxo-thiazolidin-5-one

4-(trans-2-acridin-9-yl-vinyl)-phenol

Refernces

• 1、 Rode, Chandrashekhar V.,Sonar, Mahesh V.,Nadgeri, Jayprakash M.,Chaudhari, Raghunath V.. "Selective synthesis of p-hydroxybenzaldehyde by liquid-phase catalytic oxidation of p-cresol". . p. 873 - 878. Retrieved 2004.
• 2、 Solovskii,Borisenko,Tarabukina,Amirova. "Synthesis of Copolymers of N-Vinylpyrrolidone with Crotonic Acid Modified with 4-Oxybenzaldehyde". . p. 514 - 519. Retrieved 2018.
• 3、 Neumann, Ronny,Sasson, Yoel. "Increased para Selectivity in the Reimer-Tiemann Reaction by Use of Polyethylene Glycol as Complexing Agent". . p. 569 - 570. Retrieved 1986.
• 4、 Hussain, Nazar,Delar, Emmanilo,Piochon, Marianne,Groleau, Marie-Christine,Tebbji, Faiza,Sellam, Adnane,Déziel, Eric,Gauthier, Charles. "Total synthesis of the proposed structures of gladiosides I and II". . . Retrieved 2021.
• 5、 Wang, Xujie,Liu, Fu,Yun, Juping,Feng, Ziming,Jiang, Jianshuang,Yang, Yanan,Zhang, Peicheng. "Iron-Catalyzed Synthesis of the Hexahydrocyclopenta[c]furan Core and Concise Total Synthesis of Polyflavanostilbene B". . p. 10127 - 10131. Retrieved 2018.
• 6、 Fási, Laura,Di Meo, Florent,Kuo, Ching-Ying,Stojkovic Buric, Sonja,Martins, Ana,Kúsz, Norbert,Béni, Zoltán,Dékány, Miklós,Balogh, Gy?rgy Tibor,Pesic, Milica,Wang, Hui-Chun,Trouillas, Patrick,Hunyadi, Attila. "Antioxidant-Inspired Drug Discovery: Antitumor Metabolite Is Formed in Situ from a Hydroxycinnamic Acid Derivative upon Free-Radical Scavenging". . p. 1657 - 1668. Retrieved 2019.
• 7、 Guo, Zhi-Wei,Machiya, Koji,Ma, You-An,Sih, Charles J.. "Enzymatic oxidative coupling of hydroxyphenylglycine derivatives". . p. 5679 - 5682. Retrieved 1998.
• 8、 Komiyama, Makoto,Hirai, Hidefumi. "Specific Catalysis by α-Cyclodextrin on the Dichlorocarbene Attack at Phenolate". . p. 2053 - 2056. Retrieved 1981.
• 9、 Yazaki, Kazufumi,Heide, Lutz,Tabata, Mamoru. "FORMATION OF p-HYDROXYBENZOIC ACID FROM p-COUMARIC ACID BY CELL FREE EXTRACT OF LITHOSPERMUM ERYTHRORHIZON CELL CULTURES". . p. 2233 - 2236. Retrieved 1991.
• 10、 Williams, David E.,Steino, Anne,De Voogd, Nicole J.,Mauk, A. Grant,Andersen, Raymond J.. "Halicloic acids A and B isolated from the marine sponge Haliclona sp. collected in the Philippines inhibit indoleamine 2,3-dioxygenase". . p. 1451 - 1458. Retrieved 2012.