Propyl gallate

Base Information

• Chemical Name: Propyl gallate
• CAS No.: 121-79-9
• Deprecated CAS: 56274-95-4
• Molecular Formula: C10H12O5
• Molecular Weight: 212.202
• Hs Code.: 2918.29
• European Community (EC) Number: 204-498-2
• NSC Number: 2626
• UNII: 8D4SNN7V92
• DSSTox Substance ID: DTXSID5021201
• Nikkaji Number: J2.925D
• Wikipedia: Propyl_gallate
• Wikidata: Q608726
• NCI Thesaurus Code: C76728
• RXCUI: 1311134
• Metabolomics Workbench ID: 46229
• ChEMBL ID: CHEMBL7983
• Mol file: 121-79-9.mol

Synonyms:Gallate, Propyl;Propyl Gallate

Chemical Property of Propyl gallate

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder
• Vapor Pressure: 0Pa at 20℃
• Melting Point: 146-149 °C(lit.)
• Refractive Index: 1.5140 (estimate)
• Boiling Point: 448.6 °C at 760 mmHg
• PKA: 8.11(at 25℃)
• Flash Point: 181.3 °C
• PSA: 86.99000
• Density: 1.363 g/cm³
• LogP: 1.37020
• Storage Temp.: 0-6°C
• Solubility.: ethanol: 50 mg/mL
• Water Solubility.: 0.35 g/100 mL (25 ºC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 212.06847348
• Heavy Atom Count: 15
• Complexity: 206

Purity/Quality:

98.0%min ^*data from raw suppliers

Propyl gallate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43-36/37/38
• Safety Statements: 24-37-36-26

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)O)O
• Description: Propyl gallate (also known as propyl 3, 4, 5-trihydroxybenoate) is a kind of ester formed through the condensation of gallic acid and propanol. It appears as a fine white to creamy-white crystalline powder. It has long been used as a kind of antioxidants to be supplied to foods especially animal fats and vegetable oil, being especially effective with polyunsaturated fats. Propyl gallate, as an anti-oxidant, can protect the food and oils from the attack of hydrogen peroxide and oxygen free radicals, having an effect similar to the superoxide dismutase. It can also be applied to ethers, emulsion, waxes, and transformer oil as the antioxidants. It caused contact dermatitis in a baker and in a female confectioner who fried doughnuts, primarily sensitized by her night cream; the margarine probably contained gallates. Propyl gallate is an antioxidant with antimicrobial activity. It is hepatoprotective in vitro and in vivo, preventing CCl4 induced lipoperoxidation and reduction in polysomes in rat liver. Propyl gallate (100 mg/kg, i.p.) increases expression of HIF-1α, EPO, and VEGF mRNA levels and the number of normal neurons in rat brains after 8 minutes of forebrain ischemia. Propyl gallate in combination with potassium sorbate is bactericidal and bacteriostatic against S. aureus strains known to produce enterotoxins in food. Propyl gallate is commonly added to foods to prevent autoxidation and microbial growth.
• Uses: Propyl Gallate is an antioxidant that is the n-propylester of 3,4,5-tri- hydroxybenzoic acid. natural occurrence of propyl gallate has not been reported. it is commercially prepared by esterification of gallic acid with propyl alcohol followed by distillation to remove excess alcohol. propyl gallate is an anti-oxidant with preservative properties. Propyl Gallate is a known inhibitor of Tyrosinase, a polyphenol oxidase, which is an important enzyme in pigment biosynthesis in various organisms. It has also recently been seen to boost biodiesel li pid biosynthesis in cultures. Antioxidant for cosmetics, foods, fats, oils, ethers, emulsions, waxes, transformer oils.

Technology Process of Propyl gallate

There total 10 articles about Propyl gallate 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: 98.0%

propan-1-ol (71-23-8) + 3,4,5-trihydroxybenzoic acid (149-91-7) → Propyl gallate (121-79-9,56274-95-4)

Guidance literature:

With brominated modified sulfonic acid resin; at 100 ℃; for 5h;

Reference yield: 81.0%

→ Propyl gallate (121-79-9,56274-95-4)

Guidance literature:

With sulfuric acid; Reflux;

Reference yield: 75.0%

3,4,5-trihydroxybenzoic acid (149-91-7) + butan-1-ol (71-36-3) → Propyl gallate (121-79-9,56274-95-4)

Guidance literature:

With sulfuric acid; In propan-1-ol; 2-methyl-propan-1-ol; water;

upstream raw materials:

propan-1-ol

3,4,5-trihydroxybenzoic acid

butan-1-ol

methyl galloate

Downstream raw materials:

3,4,5-tris(n-octadecan-1-yloxy)benzoic acid

propan-1-ol

3,4,5-trihydroxybenzoic acid

Propyl 3-[(4-methyl-phenyl)-sulfonyloxy]-4,5-dihydroxy benzoate

Refernces

• 1、 Nie, Guangjun,Zheng, Zhiming,Jin, Wei,Gong, Guohong,Wang, Li. "Development of a tannase biocatalyst based on bio-imprinting for the production of propyl gallate by transesterification in organic media". . p. 32 - 37. Retrieved 2012.
• 2、 Nie, Guangjun,Zhao, Rui,Sun, Wuyue,Gao, Yu,Zhu, Xiangxiang,Zheng, Zhiming,Yue, Wenjin. "Role of cyclic alkyl group in conformational instability of tannase". . p. 78 - 81. Retrieved 2016.
• 3、 Tewari,Schantz,Rekharsky,Goldberg. "Thermodynamics of the hydrolysis of 3,4,5-trihydroxybenzoic acid propyl ester (n-propylgallate) to 3,4,5-trihydroxybenzoic acid (gallic acid) and propan-1-ol in aqueous media and in toluene". . p. 171 - 185. Retrieved 1996.
• 4、 Aithal, Mahesh,Belur, Prasanna D.. "Enhancement of propyl gallate yield in nonaqueous medium using novel cell-associated tannase of bacillus massiliensis". . p. 445 - 455. Retrieved 2013.
• 5、 Bouaziz, Ahlem,Horchani, Habib,Salem, Nadia Ben,Chaari, Ali,Chaabouni, Moncef,Gargouri, Youssef,Sayari, Adel. "Enzymatic propyl gallate synthesis in solvent-free system: Optimization by response surface methodology". . p. 242 - 250. Retrieved 2010.
• 6、 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.
• 7、 -. "A preparation method of electronic grade gallic octyl ester". Paragraph 0023; 0024; 0034; 0035; 0036. . Retrieved 2019/03/31.