Mequinol

Base Information

• Chemical Name: Mequinol
• CAS No.: 150-76-5
• Molecular Formula: C7H8O2
• Molecular Weight: 124.139
• Hs Code.: 29095090
• European Community (EC) Number: 205-769-8
• ICSC Number: 1097
• NSC Number: 760357,4960
• UN Number: 3335
• UNII: 6HT8U7K3AM
• DSSTox Substance ID: DTXSID4020828
• Nikkaji Number: J2.031A
• Wikipedia: Mequinol
• Wikidata: Q2862455
• NCI Thesaurus Code: C47604
• Pharos Ligand ID: TJLDZ8D9HVJF
• Metabolomics Workbench ID: 43989
• ChEMBL ID: CHEMBL544
• Mol file: 150-76-5.mol

Synonyms:4-hydroxyanisole;4-hydroxyanisole, potassium salt;4-hydroxyanisole, sodium salt;4-methoxyphenol;hydroquinone methyl ether;hydroquinone monomethyl ether;Leucodinine B;mequinol;p-hydroxyanisole;para-methoxyphenol

Chemical Property of Mequinol

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Melting Point: 56 °C
• Refractive Index: 1.533
• Boiling Point: 243 °C at 760 mmHg
• PKA: 10.21(at 25℃)
• Flash Point: 120.8 °C
• PSA: 29.46000
• Density: 1.109 g/cm³
• LogP: 1.40080
• Storage Temp.: Refrigerator
• Solubility.: Soluble in acetone, ethyl acetate, ethanol, ether, benzene and c
• Water Solubility.: 40 g/L (25 ºC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 124.052429494
• Heavy Atom Count: 9
• Complexity: 75
• Transport DOT Label: Class 9

Purity/Quality:

99% , ^*data from raw suppliers

4-Hydroxyanisole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 24/25-26-37/39-46

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: COC1=CC=C(C=C1)O
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the skin. This may result in depigmentation.
• Chemical Composition and Structure: Mequinol, also known as 4-methoxyphenol, has the molecular formula C7H8O2. It consists of a phenolic ring with a methoxy group (-OCH3) attached to the aromatic ring at the para position.
• Categories and Type: Mequinol is categorized as a phenolic compound.^[1]
• Medical Uses: Mequinol has been incorporated into wound dressing materials due to its anti-inflammatory and antioxidant properties. It has shown potential in promoting wound healing, particularly in diabetic wounds.^[2]
• Cosmetic Uses: Mequinol is used in skincare products for its ability to inhibit melanogenesis and treat hyperpigmentation.
• Chemical Synthesis: Mequinol is utilized as an intermediate in the synthesis of various organic compounds, including polymerization inhibitors, antioxidants for foods and cosmetics, and pharmaceuticals.^[3]
• References: [1] The component analysis of liquid smoke from rice hulls and its toxicity test on baby hamster kidney cells; [2] Mequinol-loaded carboxymethyl cellulose/chitosan electrospun wound dressing as a potential candidate to treat diabetic wounds; DOI 10.1007/s10570-022-04753-w; [3] Room Temperature Synthesis of Mequinol by Using Ionic Liquids as Homogeneous Recyclable Catalysts

Technology Process of Mequinol

There total 555 articles about Mequinol 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: 74.0%

ethanol (64-17-5) + 4-methoxy-benzaldehyde (123-11-5) → ethyl 4-methoxybenzoate (94-30-4) + 4-methoxy-phenol (150-76-5) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

With dihydrogen peroxide; methyltrioxorhenium(VII); at 50 ℃; for 24h;

DOI:10.1246/cl.1995.127

Reference yield: 51.0%

4-methoxy-benzaldehyde (123-11-5) + isopropyl alcohol (67-63-0,8013-70-5) → 4-methoxy-benzoic acid isopropyl ester (6938-38-1) + 4-methoxy-phenol (150-76-5) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

With dihydrogen peroxide; methyltrioxorhenium(VII); at 50 ℃; for 24h;

DOI:10.1246/cl.1995.127

Reference yield: 50.0%

4-methoxy-benzaldehyde (123-11-5) → 4-methoxy-phenol (150-76-5) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

With disodium hydrogenphosphate; urea-hydrogen peroxide; acetic anhydride; In dichloromethane;

DOI:10.1016/S0040-4039(01)01332-6

upstream raw materials:

tetrahydrofuran

n-butyl magnesium bromide

phosgene

1-methoxy-4-phenoxy-benzene

Downstream raw materials:

4-methoxy-2-(tert-pentylsulfanyl-methyl)-phenol

2-(4-methoxyphenoxy)pyridine

1-(4-methoxyphenoxy)-2,4-dinitrobenzene

2-benzyl-4-methoxyphenol

Refernces

• 1、 Jager, Jan,Engberts, Jan B. F. N.. "Inhibition of Water-Catalyzed Ester Hydrilysis in Hydrophobic Microdomains of Poly(methacrylic acid) Hypercoils". . p. 3331 - 3334. Retrieved 1984.
• 2、 Carvalho, Emilia,Francisco, Ana Paula,Iley, Jim,Rosa, Eduarda. "The mechanism of hydrolysis of aryl ether derivatives of 3-hydroxymethyltriazenes". . p. 2056 - 2063. Retrieved 2005.
• 3、 Zhang, Fangwei,Zhang, Jiali,Guo, Shouwu. "Gold nanoparticles stabilized by graphene quantum dots as catalysts for C–C bond cleavage in β-O-4 lignin model compounds". . p. 105 - 109. Retrieved 2019.
• 4、 Holterman, Herman A. J.,Engberts, Jan B. F. N.. "Isobaric and Isochoric Activation Parameters for the Water-Catalyzed Hydrolysis of p-Methoxyphenyl 2,2-Dichloropropionate in Typically Aqueous Solutions". . p. 6382 - 6384. Retrieved 1982.
• 5、 Sherborne, Grant J.,Adomeit, Sven,Menzel, Robert,Rabeah, Jabor,Brückner, Angelika,Fielding, Mark R.,Willans, Charlotte E.,Nguyen, Bao N.. "Origins of high catalyst loading in copper(i)-catalysed Ullmann-Goldberg C-N coupling reactions". . p. 7203 - 7210. Retrieved 2017.
• 6、 Holland, Herbert L.,Conn, Morgan,Chenchaiah, P. Chinna,Brown, Frances M.. "REMOVAL OF O-AND N-BENZYL GROUPS BY FUNGAL BIOTRANSFORMATION". . p. 6393 - 6394. Retrieved 1988.
• 7、 Viallon, Loik,Reinaud, Olivia,Capdevielle, Patrice,Maumy, Michel. "Synthesis of Tetrahydroazocino- and Dihydroazepino-1,2-Benzoquinones via Amino-Claisen Rearrangement of 4-(2-Vinyl-Azetidino and Aziridino)-1,2-Benzoquinones". . p. 4787 - 4790. Retrieved 1995.
• 8、 Apperloo, Joke J.,Streefland, Lisette,Engberts, Jan B. F. N.,Blandamer, Michael J.. "Pairwise Gibbs energies of interaction involving N-alkyl-2- pyrrolidinones and related compounds in aqueous solution obtained from kinetic medium effects". . p. 411 - 418. Retrieved 2000.
• 9、 Bhatt. "-". . p. 221,222,224. Retrieved 1978.
• 10、 Hashidoko, Yasuyuki,Tahara, Satoshi,Mizutani, Junya. "2-PHENOXYCHROMONES AND A STRUCTURALLY RELATED FLAVONE FROM LEAVES OF ROSA RUGOSA". . p. 3837 - 3838. Retrieved 1991.