Octyl gallate

Base Information

• Chemical Name: Octyl gallate
• CAS No.: 1034-01-1
• Molecular Formula: C15H22O5
• Molecular Weight: 282.337
• Hs Code.: 2918.29
• European Community (EC) Number: 213-853-0
• NSC Number: 97419
• UNII: 079IIA2811
• DSSTox Substance ID: DTXSID4040713
• Nikkaji Number: J12.253J
• Wikipedia: Octyl_gallate
• Wikidata: Q2317929
• Metabolomics Workbench ID: 46022
• ChEMBL ID: CHEMBL277346
• Mol file: 1034-01-1.mol

Synonyms:3,4,5-trihydroxybenzoic acid octyl ester;octyl gallate;octyl gallate dihydrate

Chemical Property of Octyl gallate

Chemical Property:

• Appearance/Colour: white granular
• Vapor Pressure: 6E-10mmHg at 25°C
• Melting Point: 101-104 °C(lit.)
• Refractive Index: 1.552
• Boiling Point: 482.9 °C at 760 mmHg
• PKA: 7.94±0.25(Predicted)
• Flash Point: 177.1 °C
• PSA: 86.99000
• Density: 1.185 g/cm³
• LogP: 3.32070
• Storage Temp.: 0-6°C
• Solubility.: soluble2.5%, clear, colorless (AcOH (MEOH))
• Water Solubility.: 20mg/L(29.99 oC)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 282.14672380
• Heavy Atom Count: 20
• Complexity: 269

Purity/Quality:

99.0% ^*data from raw suppliers

Octyl gallate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCOC(=O)C1=CC(=C(C(=C1)O)O)O
• Description: Octyl gallate is the ester formed by 1-octanol and gallic acid. It can be used as an antioxidant and preservative to be supplemented to the food. It has been demonstrated to be an effective fungicide being capable of inhibiting the growth of S. cerevisiae and Z. bailii as it can inhibit the fluidity of the cell membrane through acting as a nonionic surface-active agent. It is also capable of killing both DNA and RNA viruses with a relatively moderate cytotoxicity. For example, it has the potential to treat influenza. Octyl gallate also has certain bactericidal activity, being capable of treating the infections associated with enterococci. During the 1940s, propyl gallate and several other alkyl gallates were allowed for use in foods in a number of countries. Since gallic acid contains three phenolic hydroxyl groups, it is a rather potent antioxidant; however, the propyl ester has a significant degree of water solubility. As a consequence, propyl gallate tends to partition into any water phase which may be present and to complex with iron salts to give bluish black colors. Also, its relatively poor resistance to heat degradation makes it ineffective for baking and frying applications. The higher alkyl gallates (butyl and octyl) are more fat soluble.
• Uses: Used in treatment of alcohol dependence. Octyl gallate is an antioxidant that is used as a preservation agent in a wide variety of foods, oils, and cosmetics. Octyl gallate is an antioxidant for use in cosmetic and pharmaceutical products and in food products, such as margarine and peanut butter.

Technology Process of Octyl gallate

There total 11 articles about Octyl 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: 96.0%

octanol (111-87-5) + 3,4,5-trihydroxybenzoic acid (149-91-7) → Octyl gallate (1034-01-1)

Guidance literature:

With sulfuric acid; at 100 ℃; for 0.833333h; Microwave irradiation;

DOI:10.1016/j.ejmech.2015.01.033

Reference yield: 94.1%

octanol (111-87-5) + Ethyl gallate (831-61-8) → Octyl gallate (1034-01-1)

Guidance literature:

With tris(pentafluorophenyl)borate; In toluene; Reflux;

Reference yield: 93.9%

octanol (111-87-5) + methyl galloate (99-24-1) → Octyl gallate (1034-01-1)

Guidance literature:

With tris(pentafluorophenyl)borate; In toluene; Solvent; Reflux;

upstream raw materials:

octanol

3,4,5-trihydroxybenzoic acid

3,4,5-trihydroxybenzoyl chloride

Ethyl gallate

Downstream raw materials:

octyl 3-O-(β-D-glucopyranosyluronate)-4,5-dihydroxybenzoate

octyl 3-O-(β-D-glucopyranosyl)-4,5-dihydroxybenzoate

octyl 3-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4,5-dihydroxybenzoate

octyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)-4,5-dihydroxybenzoate

Refernces

• 1、 Morris,Riemenschneider. "-". . p. 500. Retrieved 1946.
• 2、 Zhao, Xiao-Long,Li, Chun-Qing,Song, Xiao-Mei,Yan, Shuang-Mei,Luo, Du-Qiang. "Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo". . p. 38 - 43. Retrieved 2021/02/01.
• 3、 Arsianti, Ade,Astuty, Hendri,Fadilah,Simadibrata, Daniel Martin,Adyasa, Zoya Marie,Amartya, Daniel,Bahtiar, Anton,Tanimoto, Hiroki,Kakiuchi, Kiyomi. "Synthesis and in vitro antimalarial activity of alkyl esters of gallate as a growth inhibitor of plasmodium falciparum". . p. 655 - 662. Retrieved 2018/05/28.