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121-79-9

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Identification

Name
Propyl gallate
CAS
121-79-9
Synonyms
3,4,5-TRIHYDROXYBENZENE-1-PROPYLCARBOXYLATE
3,4,5-TRIHYDROXYBENZOIC ACID N-PROPYL ESTER
3,4,5-TRIHYDROXYBENZOIC ACID PROPYL ESTER
FEMA 2947
FEMA 2974
GALLIC ACID N-PROPYL ESTER
GALLIC ACID PROPYL ESTER
N-PROPYL 3,4,5-TRIHYDROXYBENZOATE
N-PROPYL GALLATE
PROGALLIN P
PROPYL GALLATE
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
EINECS(EC#)
204-498-2
Molecular Formula
C10H12O5
MDL Number
MFCD00002196
Molecular Weight
212.2
MOL File
121-79-9.mol

Chemical Properties

Appearance
white to light beige crystalline powder
Melting point 
146-149 °C(lit.)

mp 
146-149 °C(lit.)

Boiling point 
312.03°C (rough estimate)
density 
1.210
refractive index 
1.5140 (estimate)
FEMA 
2947
Fp 
187℃
storage temp. 
0-6°C
solubility 
ethanol: 50 mg/mL

form 
powder

pka
8.11(at 25℃)
color 
White to light beige
Water Solubility 
0.35 g/100 mL (25 ºC)
Detection Methods
HPLC,NMR
Merck 
14,7859
BRN 
1877976
Contact allergens
This 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.
InChIKey
ZTHYODDOHIVTJV-UHFFFAOYSA-N
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.
Uses
propyl gallate is an anti-oxidant with preservative properties.
CAS DataBase Reference
121-79-9(CAS DataBase Reference)
NIST Chemistry Reference
Benzoic acid, 3,4,5-trihydroxy-, propyl ester(121-79-9)
EPA Substance Registry System
Propyl gallate (121-79-9)

Hazard Information

Chemical Properties
white to light beige crystalline powder
Uses
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.
Uses
Antioxidant for cosmetics, foods, fats, oils, ethers, emulsions, waxes, transformer oils.
General Description
Fine white to creamy-white crystalline powder. Odorless or with a faint odor. Melting point 150°C. Insoluble in water. Slightly bitter taste.
Reactivity Profile
PROPYL GALLATE(121-79-9) 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 .
Air & Water Reactions
Insoluble in water.
Hazard
Use in foods restricted to 0.02% of fat con- tent.
Fire Hazard
This chemical is combustible.
Production Methods
Propyl 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.
Preparation
Produced commercially by the esterification of gallic acid with propyl alcohol followed by distillation to remove the excess alcohol.
Pharmaceutical Applications
Propyl 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.
Biochem/physiol Actions
An antioxidant that exhibits antimicrobial activity. Propyl gallate has been reported to be an effective antioxidant-based hepatoprotector, both in vitro and in vivo. It 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.
Toxicology
Propyl 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.
Safety
It 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 in neonates.
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
storage
Propyl 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 Methods
Crystallise the ester from aqueous EtOH or *C6H6 (m 146-146.5o). [Beilstein 10 III 2078, 10 IV 2003.]
Incompatibilities
The 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 Status
GRAS 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.

Safety Data

Hazard Codes 
Xn
Risk Statements 
R22:Harmful if swallowed.
R43:May cause sensitization by skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements 
S24:Avoid contact with skin .
S37:Wear suitable gloves .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
WGK Germany 
2

RTECS 
LW8400000

TSCA 
Yes
HS Code 
29182950
Safety Profile
Poison 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.
Hazardous Substances Data
121-79-9(Hazardous Substances Data)
Toxicity
LD50 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.)

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

Questions And Answer

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.
References
https://pubchem.ncbi.nlm.nih.gov/compound/propyl_gallate#section=Top
https://en.wikipedia.org/wiki/Propyl_gallate
http://www.hmdb.ca/metabolites/HMDB33835

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