Butylparaben

Base Information

• Chemical Name: Butylparaben
• CAS No.: 94-26-8
• Deprecated CAS: 8068-49-3,1350551-41-5
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• Hs Code.: 29182900
• European Community (EC) Number: 202-318-7
• NSC Number: 759303,8475
• UNII: 3QPI1U3FV8
• DSSTox Substance ID: DTXSID3020209
• Nikkaji Number: J2.842H
• Wikipedia: Butylparaben
• Wikidata: Q3302873
• NCI Thesaurus Code: C76701
• RXCUI: 1306937
• Pharos Ligand ID: 5FNSRYGXCR1G
• ChEMBL ID: CHEMBL459008
• Mol file: 94-26-8.mol

Synonyms:Benzoicacid, p-hydroxy-, butyl ester (6CI,8CI);4-(Butoxycarbonyl)phenol;4-Hydroxybenzoic acid butyl ester;Aseptoform Butyl;Butoben;Butyl4-hydroxybenzoate;Butyl Butex;Butyl Tegosept;Butyl chemosept;Butylp-hydroxybenzoate;Butyl parabens;Butyl parasept;Mekkings B;NSC 13164;NSC 8475;Nipabutyl;Preserval B;SPF;Solbrol B;Tegosept Butyl;n-Butyl 4-hydroxybenzoate;n-Butylparaben;p-Hydroxybenzoic acid butyl ester;Butyl paraben;

Chemical Property of Butylparaben

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 67-70 °C(lit.)
• Refractive Index: 1.562
• Boiling Point: 309.2 °C at 760 mmHg
• PKA: pKa 8.5 (Uncertain)
• Flash Point: 129.2 °C
• PSA: 46.53000
• Density: 1.108 g/cm³
• LogP: 2.34910
• Storage Temp.: 0-6°C
• Solubility.: Soluble in DMSO, ethyl acetate, methanol.
• Water Solubility.: <0.1 g/100 mL at 17℃
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 171

Purity/Quality:

99%MIN ^*data from raw suppliers

Butyl4-?Hydroxybenzoate(ButylParaben) ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Preservatives
• Canonical SMILES: CCCCOC(=O)C1=CC=C(C=C1)O
• Recent ClinicalTrials: Sun Protection Factor Assay (316/2016)
• Production method: Butylparaben is derived from the esterification between p-hydroxybenzoic acid and butanol. Butanol and p-hydroxybenzoic acid are heated together for being dissolved, slowly added dropwise of sulfuric acid, continue the refluxing for 8h. After cooling, add 4% sodium carbonate solution, separate the water layer, steam out the butanol, let it cool, filter to obtain the crude product, and then carry out ethanol recrystallization (solubility in ethanol: 200g/100ml).Take sulfuric acid as a catalyst; derive it from the reaction between p-hydroxybenzoic acid and butanol.
• Uses: Butylparaben is used as a preservative in some foods, cosmetics, and drug formulations. It has been added to solutions such as commercially prepared low-ionic strength saline (LISS) solutions and beer to retard microbial growth (Judd et al., 1982; Raducan et al., 1994). Parabens in general are most active against molds and yeasts and, to a lesser extent, bacteria. In comparison to other parabens, butylparaben appears to be the best antifungal agent (HSDB, 2003). preservative in many creams, lotions, ointments and other cosmetics, foods (salad dressings, mayonnaise, spiced sauces, mustard, frozen dairy products, baked products), pharmaceutical preparations and dentifrices. It is active against molds, fungi and yeasts, but less active against bacteria. ICU.
• Description: Butylparaben is an antimicrobial agent used in pharmaceutical suspensions. It is act by inhibiting DNA, RNA, and enzymes (eg, ATPase and phosphotransferase) synthesis. Butylparaben may be used alone or with other parabens, chiefly methylparaben and/or propylparaben, in medications. It is common in many liquid and solid (gel cap) OTC products such as Tylenol, Drixoral, Maalox, and Mylanta. Unfortunately, butylparaben concentrations were seldom identified for OTC or prescription products. No attempt was made to identify butylparaben-containing dietary supplements.

Technology Process of Butylparaben

There total 12 articles about Butylparaben 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%

butan-1-ol (71-36-3) + 4-hydroxy-benzoic acid (99-96-7) → 4-hydroxybenzoic acid, butyl ester (94-26-8)

Guidance literature:

With sulfuric acid; In toluene; Heating;

DOI:10.1021/jo9911138

Reference yield: 91.0%

n-butyl 4-(methoxymethoxy)benzoate (251640-53-6) → 4-hydroxybenzoic acid, butyl ester (94-26-8)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In 1,2-dichloro-ethane; at 40 ℃;

DOI:10.1081/SCC-200039382

Reference yield: 89.9%

→ 4-hydroxybenzoic acid, butyl ester (94-26-8)

Guidance literature:

With benzothiazole hydrogen sulfate; for 4h; Reflux; Green chemistry;

upstream raw materials:

butan-1-ol

4-hydroxy-benzoic acid

carbon dioxide

tetra-n-butylammonium phenolate

Downstream raw materials:

n-butyl 4-n-butoxybenzoate

4-chlorocarbonyloxy-benzoic acid butyl ester

4-(2-hydroxy-ethoxy)-benzoic acid butyl ester

C₁₂H₁₄O₄

Refernces

• 1、 Xia, Wen,Nie, Yu-Mei,Lei, Na,Tao, Zhu,Zhu, Qiang-Jiang,Zhang, Yun-Qian. "A recyclable cucurbit[6]uril-supported silicotungstic acid catalyst used in the esterification reaction". . . Retrieved 2021/05/05.
• 2、 -. "Method for preparing paraben". Paragraph 0037-0040. . Retrieved 2020/03/25.