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Propyl 3,4,5-trihydroxybenzoate is an antioxidant that protects against oxidation by hydrogen peroxide and oxygen free radicals.
Propyl 3,4,5-trihydroxybenzoate has long been used as an antioxidant in foods, especially for animal fats and vegetable oils, being especially effective with polyunsaturated fats.
Propyl 3,4,5-trihydroxybenzoate is used as a food additive under the E number E310.
CAS Number: 121-79-9
EC Number: 204-498-2
Molecular Formula: C10H12O5
Molecular Weight: 196.2 g/mol
Synonyms: Gallic acid propyl ester , PG, Propyl gallate, 98% 100GR, Propyl gallat, Propyl gallate,3,4,5-Trihydroxybenzoic acid propyl ester, Tenox PG, Propyl gallate 3g [121-79-9], Propyl gallate (200 mg)G2D2031.000mg/mg(dr), Propyl gallate (200 mg), Propyl gallate, USP, Propyl gallate SynonyMs: Propyl 3,4,5-trihydroxybenzoate, proply gallate, Propyl 3,4,5-trihydroxybenzoate 3,4,5-Trihydroxybenzoic acid propyl ester Tenox PG, Propyl 3,4,5-trihydroxybenzoate for synthesis, 3,4,5-TRIHYDROXYBENZENE-1-PROPYLCARBOXYLATE, 3,4,5-TRIHYDROXYBENZOIC ACID N-PROPYL ESTER, 3,4,5-TRIHYDROXYBENZOIC ACID PROPYL ESTER, n-propylesterof3,4,5-trihydroxybenzoicacid, Propyl galiate, propyl3,4,5-, Propylester kyseliny gallove, propylesterkyselinygallove, Sustane PG, Tenox PG, tenoxpg, GALLIC ACID N-PROPYL ESTER, GALLIC ACID PROPYL ESTER, FEMA 2947, FEMA 2974, n-Propyl gallate (Ph. Eur.) pure, pharma grade, Propyl gallate 121-79-9 Propyl 3,4,5-trihydroxybenzoate, Propyl 3,4,5-trihydroxybenzoate 121-79-9 Propyl gallate, PROGALLIN P, Propyl gallate, N-Propyl gallate, N-PROPYL 3,4,5-TRIHYDROXYBENZOATE, 3,4,5-trihydroxy-benzoicacipropylester, Benzoicacid,3,4,5-trihydroxy-,propylester, NCI-C50588, nci-c505888, Nipa 49, nipa49, Nipagallin P, nipagallinp, n-Propyl ester of 3,4,5-trihydroxybenzoic acid, L-A-PHOSPHATIDYLCHOLINE, B-OLEOYL,*GAMMA -MYRISTOYL, Propyl gallate, FOR MICROSCOPY, Propyl gallate 98+% FCC, PropylGallate(Antioxidant), PropylGallate-(N-Propyl-3,4,5-Trihydroxybezoate), Propyl gallate ,99%, Ethyl carbamate Solution, 1000ppm, Propyl gailate, Propyl gallate ,98%, Gallic acid propyl, Propyl 3,4,5-trihydroxybenzoate, 3,4,5-Trihydroxy-Benzoic, Propyl gallate USP/NF/FCC, PROPYLGALLATE,FCC, PROPYLGALLATE,NF
Propyl 3,4,5-trihydroxybenzoate is a chemical compound used primarily as an antioxidant.
Propyl 3,4,5-trihydroxybenzoate's primary function is to prevent the oxidation of fats and oils in food products, which helps to extend shelf life and maintain flavor and nutritional quality.
Propyl 3,4,5-trihydroxybenzoates often found in processed foods, cosmetics, and pharmaceuticals.
Propyl 3,4,5-trihydroxybenzoate is an ester formed by the condensation of gallic acid and propanol.
Since 1948, Propyl 3,4,5-trihydroxybenzoate has been added to foods containing oils and fats to prevent oxidation.
As a food additive, Propyl 3,4,5-trihydroxybenzoate is used under the E number E310.
Propyl 3,4,5-trihydroxybenzoate is an antioxidant.
Propyl 3,4,5-trihydroxybenzoate protects against oxidation by hydrogen peroxide and oxygen free radicals.
Propyl 3,4,5-trihydroxybenzoate is a kind of ester formed through the condensation of gallic acid and propanol.
Propyl 3,4,5-trihydroxybenzoate appears as a fine white to creamy-white crystalline powder.
Propyl 3,4,5-trihydroxybenzoate 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 3,4,5-trihydroxybenzoate, 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.
Propyl 3,4,5-trihydroxybenzoate can also be applied to ethers, emulsion, waxes, and transformer oil as the antioxidants.
Propyl 3,4,5-trihydroxybenzoate 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 3,4,5-trihydroxybenzoate is an antioxidant with antimicrobial activity.
Propyl 3,4,5-trihydroxybenzoate is hepatoprotective in vitro and in vivo, preventing CCl4 induced lipoperoxidation and reduction in polysomes in rat liver.
Propyl 3,4,5-trihydroxybenzoate in combination with potassium sorbate is bactericidal and bacteriostatic against S. aureus strains known to produce enterotoxins in food. Propyl 3,4,5-trihydroxybenzoate is commonly added to foods to prevent autoxidation and microbial growth.
Propyl 3,4,5-trihydroxybenzoate appears as fine white to creamy-white crystalline powder.
Propyl 3,4,5-trihydroxybenzoate is odorless or with a faint odor.
Propyl 3,4,5-trihydroxybenzoate's melting point 150°C.
Propyl 3,4,5-trihydroxybenzoate is insoluble in water.
Propyl 3,4,5-trihydroxybenzoate is slightly bitter taste.
Propyl 3,4,5-trihydroxybenzoate is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
Propyl 3,4,5-trihydroxybenzoate is used by professional workers (widespread uses), in formulation or re-packing and at industrial sites.
Propyl 3,4,5-trihydroxybenzoate is the n-propyl ester of gallic acid (3,4,5-trihydroxybenzoic acid).
Propyl 3,4,5-trihydroxybenzoate is soluble in ethanol, ethyl ether, oil, lard, and aqueous solutions of polyethylene glycol (PEG) ethers of cetyl alcohol, but only slightly soluble in water.
Propyl 3,4,5-trihydroxybenzoate currently is used as an antioxidant in a reported 167 cosmetic products at maximum concentrations of 0.1%.
Propyl 3,4,5-trihydroxybenzoate is a generally recognized as safe (GRAS) antioxidant to protect fats, oils, and fat-containing food from rancidity that results from the formation of peroxides.
The biological activity of Propyl 3,4,5-trihydroxybenzoate is consistent with its free-radical scavenging ability, with effects that include antimicrobial activity, enzyme inhibition, inhibition of biosynthetic processes, inhibition of the formation of nitrosamines, anesthesia, inhibition of neuromuscular response to chemicals, ionizing/ultraviolet (UV) radiation protection, chemoprotection, antimutagenesis, anticarcinogenesis and antitumorigenesis, antiteratogenesis, and anticariogenesis.
Propyl 3,4,5-trihydroxybenzoate has being shown to be a hepatoprotector in vitro and in vivo.
Propyl 3,4,5-trihydroxybenzoate is an anti-fade reagent in fluorescence microscopy to reduce photobleaching of fluorescent probes such as rhodamine and fluorescein.
An antioxidant which exhibits antimicrobial activity.
Propyl 3,4,5-trihydroxybenzoate is an antioxidant with antimicrobial activity.
Propyl 3,4,5-trihydroxybenzoate is hepatoprotective in vitro and in vivo, preventing CCl4 induced lipoperoxidation and reduction in polysomes in rat liver.
1,2 Propyl 3,4,5-trihydroxybenzoate (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 3,4,5-trihydroxybenzoate in combination with potassium sorbate is bactericidal and bacteriostatic against S. aureus strains known to produce enterotoxins in food.4 Propyl 3,4,5-trihydroxybenzoate is commonly added to foods to prevent autoxidation and microbial growth.
Propyl 3,4,5-trihydroxybenzoate, C10H12O5, is an ester formed from gallic acid and propanol.
Since 1948, this antioxidant has been added to foods containing oils and fats to prevent oxidation.
As a food additive, Propyl 3,4,5-trihydroxybenzoate is used under the E number E310.
Propyl 3,4,5-trihydroxybenzoate is an important antioxidant for the prevention of rancidity in edible oils and fats.
Gallic acid is 3,4,5-trihydroxybenzoic acid and has the formula (HO)3C6H2·CO2H.
Propyl 3,4,5-trihydroxybenzoate is found in foods, cosmetics, hair products, adhesives, and lubricants.
Propyl 3,4,5-trihydroxybenzoate is used to protect oils and fats from oxidation.
Uses of Propyl 3,4,5-trihydroxybenzoate:
Propyl 3,4,5-trihydroxybenzoate is used to protect oils and fats in products from oxidation; Propyl 3,4,5-trihydroxybenzoate is used in foods, cosmetics, hair products, adhesives, and lubricants.
Propyl 3,4,5-trihydroxybenzoate is used as a triplet state quencher and an antioxidant in fluorescence microscopy.
Propyl 3,4,5-trihydroxybenzoate is used as an antioxidant for foods and cosmetics; especially fats, oils, emulsions, and waxes.
Propyl 3,4,5-trihydroxybenzoate is also used in transformer oils and as a stabilizer for synthetic vitamin A.
Reactive peroxides in povidone often lead to degradation of oxidation-labile drugs.
The antioxidants ascorbic acid, Propyl 3,4,5-trihydroxybenzoate, and sodium sulfite reduced the peroxide concentration in povidone.
Synthetic antioxidants commonly used in food include butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), Propyl 3,4,5-trihydroxybenzoate (PG), and tert-butylhydroquinone (TBHQ).
Industry Uses:
Oxidizing/reducing agents
Consumer Uses:
Cleaning and furnishing care products
Widespread uses by professional workers:
Propyl 3,4,5-trihydroxybenzoate is used in the following products: pH regulators and water treatment products and laboratory chemicals.
Propyl 3,4,5-trihydroxybenzoate is used in the following areas: health services and scientific research and development.
Other release to the environment of Propyl 3,4,5-trihydroxybenzoate is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Uses at industrial sites:
Propyl 3,4,5-trihydroxybenzoate is used in the following products: pH regulators and water treatment products and laboratory chemicals.
Propyl 3,4,5-trihydroxybenzoate is used in the following areas: health services and scientific research and development.
Propyl 3,4,5-trihydroxybenzoate is used for the manufacture of: chemicals and textile, leather or fur.
Release to the environment of Propyl 3,4,5-trihydroxybenzoate can occur from industrial use: as processing aid, as an intermediate step in further manufacturing of another substance (use of intermediates) and in processing aids at industrial sites.
Applications of Propyl 3,4,5-trihydroxybenzoate:
Propyl 3,4,5-trihydroxybenzoate is used as an anti-fade reagent in fluorescence microscopy to reduce photobleaching of fluorescent probes such as rhodamine and fluorescein.
Pharmaceutical Applications:
Propyl 3,4,5-trihydroxybenzoate 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.
Propyl 3,4,5-trihydroxybenzoate is primarily used, in concentrations up to 0.1% w/v, to prevent the rancidity of oils and fats.
Propyl 3,4,5-trihydroxybenzoate 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 3,4,5-trihydroxybenzoate is also said to possess some antimicrobial properties;
Studies have shown that, when added to powder blends containing ketorolac, Propyl 3,4,5-trihydroxybenzoate 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.
Biological effects of Propyl 3,4,5-trihydroxybenzoate:
A 1993 study in fat rodents found little or no effect on carcinogenesis by Propyl 3,4,5-trihydroxybenzoate.
A 2009 study found that Propyl 3,4,5-trihydroxybenzoate acts as an estrogen antagonist.
Biochem/physiol Actions of Propyl 3,4,5-trihydroxybenzoate:
An antioxidant that exhibits antimicrobial activity.
Propyl 3,4,5-trihydroxybenzoate has been reported to be an effective antioxidant-based hepatoprotector, both in vitro and in vivo.
Propyl 3,4,5-trihydroxybenzoate has also been shown to prevent neuronal apoptosis and block the death of neurons exposed to FeSO4/GA as well as partially protect endothelial cells against TNF-induced apoptosis.
Propyl 3,4,5-trihydroxybenzoate has been reported to be an effective antioxidant-based hepatoprotector, both in vitro and in vivo.
Propyl 3,4,5-trihydroxybenzoate has also been shown to prevent neuronal apoptosis and block the death of neurons exposed to FeSO4/GA as well as partially protect endothelial cells against TNF-induced apoptosis.
However, Propyl 3,4,5-trihydroxybenzoate induced single strand breaks in DNA at concentrations higher than 0.25 μM when Propyl 3,4,5-trihydroxybenzoate was combined with copper concentrations at 5 μM and above.
Propyl 3,4,5-trihydroxybenzoate (Gallic acid propyl esterZ, n-Propyl 3,4,5-trihydroxybenzoate) is an antioxidant used in foods especially animal fats and vegetable oils, also in a wide variety of cosmetics and beauty care products.
Propyl 3,4,5-trihydroxybenzoate (PG) could modulate heme oxygenase-1 (HO-1) activation and decrease lung cancer cell survival.
Propyl 3,4,5-trihydroxybenzoate also induces apoptosis in human leukemia cells and HeLa cells by increasing reactive oxygen species (ROS) levels and glutathione (GSH) depletion.
Propyl 3,4,5-trihydroxybenzoate inhibits the expression of MMP-2 and MMP-9 and exerts an antimigration effect on TMZ-treated U87MG cells.
Propyl 3,4,5-trihydroxybenzoate also possesses anti-inflammatory activity via downregulation of the NF-κB pathway.
Propyl 3,4,5-trihydroxybenzoate could reduce the proliferation and augment the chemosensitivity of a THP-1 leukemia cell line via extrinsic and intrinsic apoptotic pathways.
In brain ischemia, Propyl 3,4,5-trihydroxybenzoate inhibits the activity of NF-κB, reduces COX-2 and TNF-alpha G expression, and decreases ischemic-reperfusion injury.
Chemical Properties of Propyl 3,4,5-trihydroxybenzoate:
Propyl 3,4,5-trihydroxybenzoate is an odorless powder having a slightly bitter taste.
Propyl 3,4,5-trihydroxybenzoate functions particularly well in stabilizing animal fats and vegetable oils.
With a melting point of 148°C, Propyl 3,4,5-trihydroxybenzoate loses its effectiveness during heat processing and is therefore not suitable in frying applications that involve temperatures exceeding 190°C.
Propyl 3,4,5-trihydroxybenzoate chelates iron ions and forms an unappealing, blue–black complex.
Hence, Propyl 3,4,5-trihydroxybenzoate 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).
Structure of Propyl 3,4,5-trihydroxybenzoate:
Core Structure:
A benzene ring with three hydroxyl groups (-OH) attached at the 3, 4, and 5 positions.
This gives the ring Propyl 3,4,5-trihydroxybenzoate's characteristic "gallate" structure.
A propyl ester group attached to the benzene ring through a carboxyl group (-COO-).
The ester is formed by the esterification of the carboxyl group with propanol.
Detailed Structure:
The benzene ring is the central structure with hydroxyl groups at the 3, 4, and 5 positions, which are the ortho and para positions relative to each other.
The ester linkage connects the carboxyl group of the benzene ring to a propyl group (a three-carbon chain).
Handling and Storage of Propyl 3,4,5-trihydroxybenzoate:
Handling:
Precautions:
Avoid inhalation, ingestion, and direct contact with skin and eyes.
Use appropriate personal protective equipment (PPE) such as gloves, safety goggles, and lab coats.
Ventilation:
Work in a well-ventilated area or under a fume hood to avoid inhaling dust or vapors.
Hygiene:
Wash hands thoroughly after handling Propyl 3,4,5-trihydroxybenzoate.
Avoid eating, drinking, or smoking in areas where Propyl 3,4,5-trihydroxybenzoate is used.
Storage:
Propyl 3,4,5-trihydroxybenzoate 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.
Conditions:
Store in a cool, dry place away from direct sunlight and sources of heat.
Keep containers tightly closed.
Container:
Use appropriate containers that are compatible with Propyl 3,4,5-trihydroxybenzoate.
Typically, Propyl 3,4,5-trihydroxybenzoate should be stored in airtight, moisture-proof containers.
Separation:
Keep away from strong acids, bases, and oxidizing agents to prevent potential reactions.
Reactivity and Stability of Propyl 3,4,5-trihydroxybenzoate:
Reactivity:
Conditions to Avoid:
Avoid exposure to high temperatures, strong acids, bases, and oxidizing agents.
Propyl 3,4,5-trihydroxybenzoate can decompose under extreme conditions.
Hazardous Reactions:
May react with strong acids and bases, potentially leading to hazardous decomposition products.
Stability:
Stability:
Stable under normal conditions of use and storage.
Decomposition Products:
In case of decomposition, Propyl 3,4,5-trihydroxybenzoate may produce fumes or gases that could be harmful if inhaled.
Ventilation:
Requirement:
Ensure adequate ventilation in areas where Propyl 3,4,5-trihydroxybenzoate is used.
Use local exhaust ventilation or a fume hood if working with large quantities or in a confined space.
First Aid Measures of Propyl 3,4,5-trihydroxybenzoate:
Inhalation:
Move the person to fresh air immediately.
If symptoms persist, seek medical attention.
Skin Contact:
Wash the affected area with plenty of water and soap.
Remove contaminated clothing.
Seek medical attention if irritation persists.
Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes, holding the eyelids open.
Seek medical attention immediately.
Ingestion:
Rinse the mouth with water.
Do not induce vomiting unless directed by a medical professional.
Seek medical attention immediately.
Fire Fighting Measures of Propyl 3,4,5-trihydroxybenzoate:
Suitable Extinguishers:
Use dry chemical powder, foam, or carbon dioxide (CO₂) extinguishers.
Unsuitable Extinguishers:
Avoid using water if Propyl 3,4,5-trihydroxybenzoate can spread the fire or cause hazardous reactions.
Fire Fighting Procedures:
Precautions:
Wear self-contained breathing apparatus and full protective gear.
Use water spray to cool containers exposed to fire and prevent the spread of fire.
Hazardous Combustion Products:
Possible Products:
Combustion may produce hazardous fumes or gases.
Be aware of potential exposure risks during a fire.
Accidental Release Measures of Propyl 3,4,5-trihydroxybenzoate:
Personal Precautions:
Protective Equipment:
Wear appropriate PPE, including gloves, safety goggles, and masks.
Avoid Contact:
Avoid inhaling dust or vapors and prevent contact with skin and eyes.
Containment and Cleanup:
Containment:
Isolate the area and prevent the spread of the spill.
Use barriers or absorbents to contain the material.
Cleanup:
Collect the spilled material using suitable tools and dispose of Propyl 3,4,5-trihydroxybenzoate according to local regulations.
Clean the area thoroughly with an appropriate solvent or detergent.
Disposal:
Regulations:
Follow local regulations for the disposal of chemical waste.
Ensure that disposal methods do not harm the environment.
Exposure Controls/Personal Protective Equipment of Propyl 3,4,5-trihydroxybenzoate:
Exposure Limits:
Standards:
Refer to occupational exposure limits established by regulatory agencies, though Propyl 3,4,5-trihydroxybenzoate typically does not have specific exposure limits.
PPE Recommendations:
Eye Protection:
Safety goggles or face shield.
Skin Protection:
Chemical-resistant gloves and lab coats.
Respiratory Protection:
Use an N95 respirator or higher if there is a risk of inhaling dust or vapors.
Ventilation:
Ensure adequate ventilation or use a fume hood when handling large quantities.
Identifiers of Propyl 3,4,5-trihydroxybenzoate:
CAS Number: 121-79-9
Molecular Formula: C10H12O5
Molecular Weight: 196.2 g/mol
SMILES: CCCC(=O)O[C@H]1Oc2c(C=CC)cc(c2O)O1
InChI: InChI=1S/C10H12O5/c1-2-3-4-13-10(12)8-5-6(11)7(9(8)14)15/h5-7,11-14H,2-4H2,1H3
InChIKey: XWDFUBTNVVIGKP-UHFFFAOYSA-N
EC / List no.: 204-498-2
CAS no.: 121-79-9
Mol. formula: C10H12O5
Properties of Propyl 3,4,5-trihydroxybenzoate:
Physical State: Solid (typically a white to off-white powder)
Melting Point: Approximately 125–129°C (257–264°F)
Boiling Point: Not well-defined, as it decomposes before boiling
Solubility:
In Water: Very low solubility
In Organic Solvents: Soluble in ethanol, acetone, and other organic solvents
Density: Approximately 1.29 g/cm³
Odor: Generally odorless
pH: Neutral to slightly acidic in solution
Chemical Stability: Stable under normal conditions of use and storage. However, Propyl 3,4,5-trihydroxybenzoate can decompose under high temperatures or in the presence of strong acids or bases.
Reactivity: Propyl 3,4,5-trihydroxybenzoate is relatively stable but can undergo hydrolysis under acidic or basic conditions.
Appearance: White to off-white crystalline powder
Specifications of Propyl 3,4,5-trihydroxybenzoate:
Purity:
Minimum Purity: Often required to be at least 98% or higher by weight.
Test Method: Typically determined by high-performance liquid chromatography (HPLC) or similar analytical techniques.
Appearance:
Color: White to off-white crystalline powder.
Odor: Odorless or with a faint characteristic odor.
Melting Point:
Range: Approximately 125–129°C (257–264°F).
Loss on Drying:
Maximum Limit:
Usually less than 1% to ensure that the substance is not excessively hygroscopic.
Heavy Metals:
Maximum Limit:
Typically less than 10 ppm (parts per million) or as specified by regulatory standards to ensure safety.
Arsenic:
Maximum Limit:
Usually less than 1 ppm.
Assay:
Minimum:
Should meet the assay requirements of 98% or higher as determined by specific analytical methods.
Residue on Ignition:
Maximum Limit:
Often less than 0.1% to ensure purity.
Acidity/Alkalinity:
Should be neutral or slightly acidic.
Names of Propyl 3,4,5-trihydroxybenzoate:
IUPAC Names:
3,4,5-trihydroxy-2-propyl-benzoate
3,4,5-Trihydroxybenzoic acid propyl ester, Propyl gallate, Gallic acid propyl ester
n-Propilo 3,4,5 Trihidroxi Benzoato
n-Propyl 3,4,5-trihydroxybenzoate
n-Propylgallate
Propyl 3,4,5 trihydroxybenzoate
Propyl 3,4,5-trihydroxybenzoate
propyl 3,4,5-trihydroxybenzoate
Propyl 3,4,5-trihydroxybenzoate
Propyl gallate
Propyl-3,4,5-trihydroxybenzoat
propyl-3,4,5-trihydroxybenzoate
