Propyl gallate Chemical Properties
- Melting point:146-149 °C(lit.)
- Boiling point:312.03°C (rough estimate)
- Density 1.210
- FEMA 2947 | PROPYL GALLATE
- refractive index 1.5140 (estimate)
- Flash point:187℃
- storage temp. 0-6°C
- solubility ethanol: 50 mg/mL
- pka8.11(at 25℃)
- form powder
- color White to light beige
- Water Solubility 0.35 g/100 mL (25 ºC)
- Merck 14,7859
- BRN 1877976
- CAS DataBase Reference121-79-9(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzoic acid, 3,4,5-trihydroxy-, propyl ester(121-79-9)
- EPA Substance Registry SystemPropyl gallate (121-79-9)
- Hazard Codes Xn
- Risk Statements 22-43-36/37/38
- Safety Statements 24-37-36-26
- WGK Germany 2
- RTECS LW8400000
- TSCA Yes
- HS Code 29182950
- Hazardous Substances Data121-79-9(Hazardous Substances Data)
- ToxicityLD50 in mice, rats, hamsters, rabbits (g/kg): 1.70-3.50, 2.1-7, 2.48, 2.75 orally; LD50 i.p. in rats: 0.38 g/kg (J. Am. Coll. Toxicol.)
Propyl gallate Usage And Synthesis
- DescriptionPropyl 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.
- DescriptionIt 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.
- Chemical PropertiesPropyl gallate is an odorless powder having a slightly bitter taste. It functions particularly well in stabilizing animal fats and vegetable oils. With a melting point of 148°C, propyl gallate loses its effectiveness during heat processing and is therefore not suitable in frying applications that involve temperatures exceeding 190°C. Propyl gallate chelates iron ions and forms an unappealing, blue–black complex. Hence, it is always used with chelators such as citric acid to eliminate the pro-oxidative iron and copper catalysts. Good synergism is obtained with BHA and BHT; however, application with TBHQ is not permitted. For additional details, refer to Burdock (1997).
- Chemical Propertieswhite to light beige crystalline powder
- Chemical PropertiesPropyl gallate is a white, odorless or almost odorless crystalline powder, with a bitter astringent taste that is not normally noticeable at the concentrations employed as an antioxidant.
- UsesPropyl 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.
- Usespropyl gallate is an anti-oxidant with preservative properties.
- UsesPropyl 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.
- UsesAntioxidant for cosmetics, foods, fats, oils, ethers, emulsions, waxes, transformer oils.
- PreparationProduced commercially by the esterification of gallic acid with propyl alcohol followed by distillation to remove the excess alcohol.
- Production MethodsPropyl gallate is prepared by the esterification of 3,4,5-trihydroxybenzoic acid (gallic acid) with n-propanol. Other alkyl gallates are prepared similarly using an appropriate alcohol of the desired alkyl chain length.
- General DescriptionFine white to creamy-white crystalline powder. Odorless or with a faint odor. Melting point 150°C. Insoluble in water. Slightly bitter taste.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfilePropyl gallate can react with oxidizing agents. Incompatible with strong acids, strong bases and strong reducing agents. Darkens in the presence of iron and iron salts. Contact with metals should be avoided .
- HazardUse in foods restricted to 0.02% of fat con- tent.
- Fire HazardPropyl gallate is combustible.
- Pharmaceutical ApplicationsPropyl gallate has become widely used as an antioxidant in
cosmetics, perfumes, foods, and pharmaceuticals since its use in
preventing autoxidation of oils was first described in 1943.It is
primarily used, in concentrations up to 0.1% w/v, to prevent the
rancidity of oils and fats;it may also be used at concentrations of
0.002% w/v to prevent peroxide formation in ether, and at 0.01%
w/v to prevent the oxidation of paraldehyde. Synergistic effects with
other antioxidants such as butylated hydroxyanisole and butylated hydroxytoluene have been reported. Propyl gallate is also said to
possess some antimicrobial properties;
Studies have shown that, when added to powder blends containing ketorolac, propyl gallate significantly increases the drug stability in the preparation.
Other alkyl gallates are also used as antioxidants and have approximately equivalent antioxidant properties when used in equimolar concentration; however, solubilities vary;
Propyl gallate has also been investigated for its therapeutic properties, mainly in animal studies.
- Contact allergensThis gallate ester (E 311) is an antioxidant frequently used in the food, cosmetic, and pharmaceutical industries to prevent the oxidation of unsaturated fatty acids into rancid-smelling compounds. It causes cosmetic dermatitis mainly from lipsticks and induced contact dermatitis in a baker, and in a female confectioner, primarily sensitized by her night cream, who fried doughnuts the margarine probably containing gallates.
- Safety ProfilePoison by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes.
- ToxicologyPropyl gallate (n-propyl-3,4,5-trihydroxybenzoate) is used in vegetable oils and butter. When 1.2 or 2.3% propyl gallate was added to feed for rats, loss of weight was observed. This may be due to the rats reluctance to eat food that was contaminated with the bitter taste of propyl gallate. When it was given for 10 to 16 months at the 2 to 3% level, 40% of the rats died within the first month and the remainder showed severe growth inhibition. Autopsies of rats indicated kidney damage resulting from the ingestion of propyl gallate. However, no other animal studies show serious problems and further studies indicated that propyl gallate does not cause serious chronic toxicities.
- SafetyIt has been reported, following animal studies, that propyl gallate
has a strong contact sensitization potential.Propyl gallate has
also produced cytogenic effects in CHO-K1 cells.However,
despite this, there have been few reports of adverse reactions to
propyl gallate.Those that have been described include contact
dermatitis, allergic contact dermatitis,and methemoglobinemia
The WHO has set an estimated acceptable daily intake for propyl gallate at up to 1.4 mg/kg body-weight.
(cat, oral): 0.4 g/kg
(mouse, oral): 1.7 g/kg
(rat, oral): 2.1 g/kg
(rat, IP): 0.38 g/kg
- storagePropyl gallate is unstable at high temperatures and is rapidly
destroyed in oils that are used for frying purposes.
The bulk material should be stored in a well-closed, nonmetallic container, protected from light, in a cool, dry place.
- Purification MethodsCrystallise the ester from aqueous EtOH or *C6H6 (m 146-146.5o). [Beilstein 10 III 2078, 10 IV 2003.]
- IncompatibilitiesThe alkyl gallates are incompatible with metals, e.g. sodium, potassium, and iron, forming intensely colored complexes. Complex formation may be prevented, under some circumstances, by the addition of a sequestering agent, typically citric acid. Propyl gallate may also react with oxidizing materials.
- Regulatory StatusGRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM injections; oral, and topical preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Propyl gallate Preparation Products And Raw materials
- 8-(DIETHYLAMINO)OCTYL 3,4,5-TRIMETHOXYBENZOATE HYDROCHLORIDE ISOBUTYL GALLATE DECYL GALLATE Dodecyl gallate Hexadecyl 3,4,5-trihydroxybenzoate MYRISTYL GALLATE Reserpine Octyl gallate 4-Hydroxybenzoic acid 3,5-Dihydroxybenzoic acid Methyl gallate 2,3,4-Trihydroxybenzoic acid PROPYL BENZOATE 3,4-Dihydroxybenzoic acid Propyl acetate Pyrogallol 2'-Hydroxy-3-phenylpropiophenone 2,6-Dihydroxybenzoic acid
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