1166-52-5

Basic information

• Product Name: Dodecyl gallate
• Synonyms: N-DODECYL GALLATE;3,4,5-TRIHYDROXYBENZOIC ACID DODECYL ESTER;DODECYL 3,4,5-TRIHYDROXYBENZOATE;DODECYL GALLATE;LAURYL GALLATE;GALLIC ACID LAURYL ESTER;GALLIC ACID N-DODECYL ESTER;GALLIC ACID DODECYL ESTER
• CAS NO: 1166-52-5
• Molecular Formula: C₁₉H₃₀O₅
• Molecular Weight: 338.44
• EINECS: 214-620-6
• Product Categories: Aromatic Esters
• Mol File: 1166-52-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 94-97 °C(lit.)
• Boiling Point: 394.57°C (rough estimate)
• Flash Point: 180.3 °C
• Appearance: white to cream powder
• Density: 1.0677 (rough estimate)
• Vapor Pressure: 1.67E-11mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Very slightly soluble or practically insoluble in water, freely soluble in ethanol (96 per cent), slightly soluble in methylene chloride.
• PKA: 7.93±0.25(Predicted)
• Water Solubility: practically insoluble
• Sensitive: Air Sensitive
• BRN: 2701981
• CAS DataBase Reference: Dodecyl gallate(CAS DataBase Reference)
• NIST Chemistry Reference: Dodecyl gallate(1166-52-5)
• EPA Substance Registry System: Dodecyl gallate(1166-52-5)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 24-37
• RIDADR: 3335
• WGK Germany: 1
• RTECS: DH9100000
• TSCA: Yes
• Hazardous Substances Data: 1166-52-5(Hazardous Substances Data)

Usage

Description

This gallate ester (E 310) is an antioxidant added to foods and cosmetics to prevent oxidation of unsaturated fatty acids. Cases have been reported in workers in the food industry, gallate being contained in margarine. It is also present in washing powder.

Chemical Properties

white to cream powder

Uses

Different sources of media describe the Uses of 1166-52-5 differently. You can refer to the following data:
1. Dodecyl Gallate is an antioxidant used in cream cheese, instant mashed potatoes, margarine, fats, and oils.
2. Dodecyl gallate is an antioxidant in cosmetic and pharmaceutical creams and emulsions, various fats, oils, waxes, and foods, such as margarine.
3. Dodecyl 3,4,5-Trihydroxybenzoate is used in method for stabilizing the pH of an aqueous compound comprising drug.

General Description

Lauryl gallate is a major monomer flavanol found in green tea and shows antioxidant activity in polymers.

Contact allergens

This gallic acid ester (E 310) is an antioxidant added to food and cosmetics to prevent oxidation of unsaturated fatty acids. Cases were reported in workers of the food industry, gallate being contained in margarine, and from washing powder.

Safety Profile

Poison by ingestion and inhalation. Moderately toxic by skin contact. A severe eye irritant. Questionable carcinogen with experimental tumorigenic data. A pesticide. When heated to decomposition it emits very toxic fumes of NOx.

Carcinogenicity

In a 2-year feeding study, with the administration of up to 5 mg/kg of feed to rats, no increase in tumor incidence was noted . In female mice, a dermal injection of dodecyl gallate (100 nmol in 0.2mL acetone) inhibits the formation of skin carcinomas and papillomas induced by the tumor promoter phorbol myristate and the initiator 7,12-dimethylbenz[a]anthracene .

InChI:InChI=1/C19H30O5/c1-2-3-4-5-6-7-8-9-10-11-12-24-19(23)15-13-16(20)18(22)17(21)14-15/h13-14,20-22H,2-12H2,1H3

Upstream product

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 1063201-08-0 dodecyl 3,4,5-tribenzyloxybenzoate 
• 112-53-8 1-dodecyl alcohol 
• 35388-10-4 3,4,5-trihydroxybenzoyl chloride 

Downstream Products

• 1329454-80-9 dodecyl 3-O-(β-D-glucopyranosyl)-4,5-dihydroxybenzoate 
• 1329454-67-2 dodecyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)-4,5-dihydroxybenzoate 

Relevant articles and documents

Inhibitory effect of gallic acid and its esters on 2,2'-azobis(2- amidinopropane)hydrochloride (AAPH)-induced hemolysis and depletion of intracellular glutathione in erythrocytes

The protective effect of gallic acid and its esters, methyl, propyl, and lauryl gallate, against 2,2'-azobis(2-amidinopropane)hydrochloride (AAPH)-induced hemolysis and depletion of intracellular glutathione (GSH) in erythrocytes was studied. The inhibition of hemolysis was dose-dependent, and the esters were significantly more effective than gallic acid. Gallic acid and its esters were compared with regard to their reactivity to free radicals, using the DPPH and AAPH/pyranine free-cell assays, and no significant difference was obtained. Gallic acid and its esters not only failed to inhibit the depletion of intracellular GSH in erythrocytes induced by AAPH but exacerbated it. Similarly, the oxidation of GSH by AAPH or horseradish peroxidase/H 2O2 in cell-free systems was exacerbated by gallic acid or gallates. This property could be involved in the recent findings on pro-apoptotic and pro-oxidant activities of gallates in tumor cells. We provide evidence that lipophilicity and not only radical scavenger potency is an important factor regarding the efficiency of antihemolytic substances.

Synthetic method of dodecyl gallate

The invention relates to a synthesis method of dodecanoyl gallate. The synthesis method comprises the following steps: 1) carrying out a primary reaction to obtain a dodecanoyl gallate crude product and an applied mother liquor; 2) applying the mother liquor to obtain a dodecanoyl gallate crude product; and 3) preparing a dodecanoyl gallate refined product by combining the crude product. The preparation method mainly comprises the following steps: carrying out a primary reaction on anhydrous gallic acid and a dodecanol to obtain a crude product and a mother liquor, carrying out an applying reaction on anhydrous gallic acid, dodecanol and the mother liquor to obtain a dodecanoyl gallate crude product, and finally preparing the refined product from the crude products obtained by the two reactions. The reaction synthesis method is simple, the raw material utilization rate is high, the product purity can reach more than 99%, and the product yield can reach more than 75%.

Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors

Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV. Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties. The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used.