Propylparaben

Base Information

• Chemical Name: Propylparaben
• CAS No.: 94-13-3
• Deprecated CAS: 59593-07-6,58339-85-8,58339-85-8
• Molecular Formula: C10H12O3
• Molecular Weight: 180.203
• Hs Code.: 29182930
• European Community (EC) Number: 202-307-7,920-388-3
• NSC Number: 23515,8511
• UNII: Z8IX2SC1OH
• DSSTox Substance ID: DTXSID4022527
• Nikkaji Number: J3.943H
• Wikipedia: Propylparaben
• Wikidata: Q511627
• NCI Thesaurus Code: C76730
• RXCUI: 34706
• Metabolomics Workbench ID: 45619
• ChEMBL ID: CHEMBL194014
• Mol file: 94-13-3.mol

Synonyms:3(or 4)-hydroxybenzoic acid propyl ester;4-hydroxybenzoic acid propyl ester;Bayer D 206;Nipazol;p-hydroxybenzoic acid propyl ester;PEPH;propyl 4-hydroxybenzoate;propyl p-hydroxybenzoate;propylparaben;propylparaben, monosodium salt

Chemical Property of Propylparaben

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00093mmHg at 25°C
• Melting Point: 95-98 °C(lit.)
• Refractive Index: 1.5050
• Boiling Point: 294.3 °C at 760 mmHg
• PKA: pKa 8.4 (Uncertain)
• Flash Point: 124.6 °C
• PSA: 46.53000
• Density: 1.134 g/cm³
• LogP: 1.95900
• Storage Temp.: 0-6°C
• Solubility.: ethanol: soluble0.1M, clear, colorless
• Water Solubility.: <0.1 g/100 mL at 12℃
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 180.078644241
• Heavy Atom Count: 13
• Complexity: 160

Purity/Quality:

99%, ^*data from raw suppliers

Propyl paraben ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Preservatives
• Canonical SMILES: CCCOC(=O)C1=CC=C(C=C1)O
• Description: Propylparaben occurs as odorless, tasteless, colorless crystals, or a white crystalline powder. The reported dissociation constant (pKa) of propylparaben is 8.4 at 22°C. Propylparaben has been reported to be very slightly soluble in water, but freely soluble in alcohol and ether. Crystals of propylparaben are translucent and colorless, belonging to the monoclinic system. The melting point of propylparaben is reported to be 95–99°C. Propylparaben is known to be stable in contact with air, but the bulk substance should still be stored in a cool, dry place in a well-closed container.
• Chemical Composition and Structure: Propylparaben is an ester of p-hydroxybenzoic acid (PHBA), specifically the propyl ester.^[1]
• Uses: Used as preservatives in cosmetics to prevent microbial growth and extend shelf life. Parabens, including propylparaben, are utilized in over 22,000 cosmetics as preservatives.^[1]; Propylparaben (PP) is one paraben that has been widely used in personal care products, cosmetics, pharmaceuticals, and food.^[2]; P-hydroxybenzoic esters (parabens) have been used as preservatives for over 70 years. In modern food technology, Methylparaben (MP) and propylparaben (PP) are the most commonly used parabens and are often used together to stop or delay nutritional losses due to microbiological, enzymatic, or chemical changes thus increasing their shelf life. since they have synergistic effects.^[4]
• Regulatory Status: The European Union authorizes the use of PPB in cosmetic products with a maximum concentration of 0.4% (EU Cosmetics Directive 76/768/EEC).^[3]
• Production Methods: Propylparaben and other parabens are typically synthesized through chemical processes, involving the esterification of PHBA with propyl alcohol or other alkyl alcohols.^[1]
• References: [1] Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products (DOI 10.1080/10915810802548359 ); [2] Assessing the Public Health Implications of the Food Preservative Propylparaben: Has This Chemical Been Safely Used for Decades (DOI 10.1007/s40572-020-00300-6 ); [3] Oxidative DNA damage contributes to the toxic activity of propylparaben in mammalian cells (DOI 10.1016/j.mrgentox.2010.07.012 )[1] Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products (DOI 10.1080/10915810802548359 ); [2] Assessing the Public Health Implications of the Food Preservative Propylparaben: Has This Chemical Been Safely Used for Decades (DOI 10.1007/s40572-020-00300-6 ); [4] Simultaneous determination of preservatives (benzoic acid, sorbic acid, methylparaben and propylparaben) in foodstuffs using high-performance liquid chromatography (DOI 10.1016/j.chroma.2004.10.105 )

Technology Process of Propylparaben

There total 12 articles about Propylparaben 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: 95.0%

n-propyl 4-acetoxybenzoate (27739-13-5) → nipasol (94-13-3)

Guidance literature:

With sodium; diphenyldisulfane; In 1-methyl-pyrrolidin-2-one; at 90 ℃; for 0.5h;

DOI:10.1021/jo010611p

Reference yield: 93.8%

propan-1-ol (71-23-8) + 4-hydroxy-benzoic acid (99-96-7) → nipasol (94-13-3)

Guidance literature:

With methanesulfonic acid; choline chloride; Reflux;

Reference yield: 90.0%

n-propyl 4-benzoyloxybenzoate → nipasol (94-13-3)

Guidance literature:

With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 100 ℃; for 3h;

DOI:10.1016/S0040-4020(01)00922-X

upstream raw materials:

propan-1-ol

4-hydroxy-benzoic acid

n-propyl 4-acetoxybenzoate

carbon dioxide

Downstream raw materials:

propyl 4-ethoxybenzoate

3-chloromethyl-4-hydroxy-benzoic acid propyl ester

3,5-dibromo-4-hydroxy-benzoic acid propyl ester

4-hydroxy-3-nitro-benzoic acid propyl ester

Refernces

• 1、 -. "Proline ionic liquid and method for catalyzing synthesis of paraben by proline ionic liquid". Paragraph 0051-0054. . Retrieved 2020/09/16.
• 2、 -. "Method for preparing parabens". Paragraph 0026; 0030-0032; 0048; 0050-0053. . Retrieved 2019/07/01.