4-Methoxybenzaldehyde

Base Information

• Chemical Name: 4-Methoxybenzaldehyde
• CAS No.: 123-11-5
• Deprecated CAS: 26249-15-0,68894-36-0,721942-53-6,2409679-18-9,68894-36-0,721942-53-6
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 29124900
• European Community (EC) Number: 204-602-6
• NSC Number: 5590
• UNII: 9PA5V6656V
• DSSTox Substance ID: DTXSID2026997
• Nikkaji Number: J3.618H
• Wikipedia: 4-Anisaldehyde
• Wikidata: Q174937
• Metabolomics Workbench ID: 43983
• ChEMBL ID: CHEMBL161598
• Mol file: 123-11-5.mol

Synonyms:4-anisaldehyde;4-anisaldehyde, 1,2,3,4,5,6-(14)C6-labeled;4-anisaldehyde, 18O-labeled;4-anisaldehyde, formyl-(14)C-labeled;4-methoxybenzaldehyde;anisaldehyde;p-anisaldehyde;p-methoxybenzaldehyde;para-anisaldehyde

Chemical Property of 4-Methoxybenzaldehyde

Chemical Property:

• Appearance/Colour: Clear to slight yellow liquid
• Vapor Pressure: 0.0249mmHg at 25°C
• Melting Point: -1 ºC
• Refractive Index: 1.571 - 1.574
• Boiling Point: 248 ºC at 760 mmHg
• Flash Point: 108.9 ºC
• PSA: 26.30000
• Density: 1.088 g/cm³
• LogP: 1.50770
• Storage Temp.: Refrigerator
• Sensitive.: Air Sensitive
• Solubility.: 2g/l
• Water Solubility.: Miscible with acetone, alcohol, ether, chloroform and benzene. Immiscible with water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 104

Purity/Quality:

98% ^*data from raw suppliers

p-Anisaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi,T,F
• Statements: 22-36/37/38-39/23/24/25-23/24/25-11-R22-36/38
• Safety Statements: 26-36-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzaldehydes
• Canonical SMILES: COC1=CC=C(C=C1)C=O
• Chemical Properties: p-Anisaldehyde (PAA), also known as 4-methoxybenzaldehyde, is an aromatic aldehyde. It is one of the isomers of anisaldehyde (C8O2H8). PAA is primarily extracted from Pimpinella anisum L. and is a trans isomer of anisole.
• Sources and Industrial Applications: PAA is naturally occurring and is found in essential oils derived from seeds of Pimpinella anisum, anise, cumin, fennel, and garlic. It is widely used in the food, beverages, and pharmaceutical industries both as a final product and as an intermediate compound for other reactions. The industrial production of PAA typically involves the oxidation or methylation of p-cresol or anisole, often under hazardous conditions.
• Antimicrobial Activity: PAA exhibits broad-spectrum antimicrobial activity against various microorganisms, including bacteria (Staphylococcus aureus, Bacillus subtilis, Listeria monocytogenes, Pseudomonas aeruginosa), yeasts (Candida, Saccharomyces cerevisiae), and molds (Aspergillus niger). It has been used for the preservation of fruits and vegetables due to its safety and antimicrobial properties.
• Safety and Regulatory Status: The United States Food and Drug Administration (FDA) has categorized PAA as "generally recognized as safe" (GRAS) for its application in food products as a natural additive. Previous studies have demonstrated the safety and efficacy of PAA in inhibiting the growth of various pathogens, including Candida albicans, Penicillium italicum, Staphylococcus aureus, Listeria monocytogenes, and Pseudomonas aeruginosa.
• Potential Applications: Recent research suggests potential applications of PAA in regulating postharvest physiological and biochemical behavior of horticultural products. Combinations of PAA with other substances, such as 尾-cyclodextrin, have shown effectiveness in suppressing the growth of fungi and preserving the storage quality of fruits like strawberries.

Technology Process of 4-Methoxybenzaldehyde

There total 1651 articles about 4-Methoxybenzaldehyde 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: 83.0%

p-methoxyl benzaldoxime (3717-21-3,3717-22-4,140461-28-5,140461-29-6,3235-04-9) → 4-methoxy-benzaldehyde (123-11-5) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

With hydrogenchloride; sodium chlorite; water; at 20 ℃; for 0.0833333h;

DOI:10.2174/157017861201150112125024

Reference yield: 77.0%

1,2-bis(4-methoxyphenyl)-1,2-ethanediol (4464-76-0,39090-28-3,39090-30-7,42565-21-9,66768-20-5,122798-27-0) → 4-methoxy-benzaldehyde (123-11-5) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

meso-tetrakis(tetraphenyl)porphyrin iron(III) chloride; 1-Benzyl-1,4-dihydronicotinamide; oxygen; In dichloromethane; for 8h; Product distribution; Mechanism; Ambient temperature; Irradiation; also in the presence of t-BuOOH in place of BNAH-O₂ in the dark;

DOI:10.1039/c39850000381

Reference yield: 59.0%

rac-1-(4-methoxyphenyl)-ethanol (3319-15-1) → 4-methoxy-benzaldehyde (123-11-5) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

With sulfuric acid; cis-nitrous acid; In water; at 25 ℃;

DOI:10.1039/c39870000870

upstream raw materials:

N-Formylpiperidine

methoxybenzene

Estragole

p-methylanizole

Downstream raw materials:

4-(4-methoxy-benzylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one

(E)-3-(4-methoxyphenyl)-N-phenylacrylamide

4-(4-methoxy-trans-styryl)-7-methyl-coumarin

1,2-bis(4-methoxyphenyl)ethene

Refernces

• 1、 Majumder, Ishani,Chatterjee, Sourav,Fischer, Roland C.,Neogi, Swarup Kumar,Mautner, Franz A.,Chattopadhyay, Tanmay. "Syntheses of U3O8 nanoparticles form four different uranyl complexes: Their catalytic performance for various alcohol oxidations". . p. 112 - 122. Retrieved 2017.
• 2、 Shiozaki, Masao,Tashiro, Takuya,Koshino, Hiroyuki,Shigeura, Tomokuni,Watarai, Hiroshi,Taniguchi, Masaru,Mori, Kenji. "Synthesis and biological activity of hydroxylated analogs of RCAI-80". . p. 9710 - 9725. Retrieved 2013.
• 3、 Noshiranzadeh, Nader,Bikas, Rahman,?lepokura, Katarzyna,Mayeli, Mina,Lis, Tadeusz. "Synthesis, characterization and catalytic activity of new Cr(III) complex in oxidation of primary alcohols to aldehydes". . p. 176 - 182. Retrieved 2014.
• 4、 Leise, Austin R.,Comas, Nicole,Harrison, Doug,Patel, Dipak,Whitemiller, Eileen G.,Wilson, Jennifer,Timms, Jacob,Golightly, Ian,Hamaker, Christopher G.,Hitchcock, Shawn R.. "A ceric ammonium nitrate based oxidative cleavage pathway for the asymmetric aldol adducts of oxadiazinones derived from (1R,2S)-N-p-methoxybenzylnorephedrine". . p. 1154 - 1162. Retrieved 2017.
• 5、 Ito, Junko,Takaya, Yoshiaki,Oshima, Yoshiteru,Niwa, Masatake. "New oligostilbenes having a benzofuran from Vitis vinifera 'Kyohou'". . p. 2529 - 2544. Retrieved 1999.
• 6、 Mizuno, Kazuhiko,Murakami, Kazuhiro,Kamiyama, Nobuhiro,Otsuji, Yoshio. "9,10-Dicyanoanthracene-sensitized Photo-oxygenation of trans-1,2-Di(carbazol-9-yl)cyclobutane via Electron-transfer". . p. 462 - 463. Retrieved 1983.
• 7、 Hailes,Raphael,Staunton. "A biomimetic approach to the synthesis of rocaglamide based on a photochemical [2 + 2] cycloaddition of a cinnamate unit to a flavone". . p. 5313 - 5316. Retrieved 1993.
• 8、 Berger, Ralf G.,Ersoy, Franziska,Krahe, Nina-Katharina. "A DyP-type peroxidase of pleurotus sapidus with alkene cleaving activity". . . Retrieved 2020.
• 9、 Rajagopalan, Aashrita,Seisser, Birgit,Mutti, Francesco G.,Schober, Markus,Kroutil, Wolfgang. "Alkene cleavage by white-rot Trametes hirsuta: Inducing enzyme activity by a fungicide". . p. 118 - 122. Retrieved 2013.
• 10、 O'Ferrall, Rory A. More,O'Brien, Deirdre. "Rate and equilibrium constants for hydrolysis and isomerization of (E)- and (Z)-p-methoxybenzaldehyde oximes". . p. 631 - 640. Retrieved 2004.