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121-79-9

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121-79-9 Usage

Description

Different sources of media describe the Description of 121-79-9 differently. You can refer to the following data:
1. 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.
2. It 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.
3. Propyl gallate is an antioxidant with antimicrobial activity. It is hepatoprotective in vitro and in vivo, preventing CCl4 induced lipoperoxidation and reduction in polysomes in rat liver. Propyl gallate (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 gallate in combination with potassium sorbate is bactericidal and bacteriostatic against S. aureus strains known to produce enterotoxins in food. Propyl gallate is commonly added to foods to prevent autoxidation and microbial growth.

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

Chemical Properties

Different sources of media describe the Chemical Properties of 121-79-9 differently. You can refer to the following data:
1. Propyl 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).
2. white to light beige crystalline powder
3. Propyl 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.

Uses

Different sources of media describe the Uses of 121-79-9 differently. You can refer to the following data:
1. 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.
2. propyl gallate is an anti-oxidant with preservative properties.
3. 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.
4. Antioxidant for cosmetics, foods, fats, oils, ethers, emulsions, waxes, transformer oils.

Preparation

Produced commercially by the esterification of gallic acid with propyl alcohol followed by distillation to remove the excess alcohol.

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.

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.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Propyl 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 .

Hazard

Use in foods restricted to 0.02% of fat con- tent.

Fire Hazard

Propyl gallate is combustible.

Flammability and Explosibility

Notclassified

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.

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.

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 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.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 121-79-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 121-79:
(5*1)+(4*2)+(3*1)+(2*7)+(1*9)=39
39 % 10 = 9
So 121-79-9 is a valid CAS Registry Number.
InChI:InChI:1S/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3

121-79-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (G0018)  Propyl Gallate  >98.0%(T)

  • 121-79-9

  • 25g

  • 180.00CNY

  • Detail
  • TCI America

  • (G0018)  Propyl Gallate  >98.0%(T)

  • 121-79-9

  • 500g

  • 1,390.00CNY

  • Detail
  • Alfa Aesar

  • (A10877)  n-Propyl 3,4,5-trihydroxybenzoate, 98%   

  • 121-79-9

  • 5g

  • 159.0CNY

  • Detail
  • Alfa Aesar

  • (A10877)  n-Propyl 3,4,5-trihydroxybenzoate, 98%   

  • 121-79-9

  • 100g

  • 295.0CNY

  • Detail
  • Alfa Aesar

  • (A10877)  n-Propyl 3,4,5-trihydroxybenzoate, 98%   

  • 121-79-9

  • 500g

  • 1404.0CNY

  • Detail
  • Alfa Aesar

  • (A10877)  n-Propyl 3,4,5-trihydroxybenzoate, 98%   

  • 121-79-9

  • 2500g

  • 3758.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1118)    pharmaceutical secondary standard; traceable to USP and PhEur

  • 121-79-9

  • PHR1118-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (P3640000)  Propylgallate  European Pharmacopoeia (EP) Reference Standard

  • 121-79-9

  • P3640000

  • 1,880.19CNY

  • Detail
  • USP

  • (1576800)  Propylgallate  United States Pharmacopeia (USP) Reference Standard

  • 121-79-9

  • 1576800-200MG

  • 4,662.45CNY

  • Detail
  • Sigma

  • (P3130)  Propylgallate  powder

  • 121-79-9

  • P3130-100G

  • 604.89CNY

  • Detail
  • Sigma

  • (P3130)  Propylgallate  powder

  • 121-79-9

  • P3130-500G

  • 2,203.11CNY

  • Detail
  • Sigma-Aldrich

  • (48710)  Propylgallate  antioxidant, ≥98.0% (HPLC)

  • 121-79-9

  • 48710-100G-F

  • 643.50CNY

  • Detail

121-79-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Propyl gallate

1.2 Other means of identification

Product number -
Other names nipa49

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:121-79-9 SDS

121-79-9Synthetic route

propan-1-ol
71-23-8

propan-1-ol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Propyl gallate
121-79-9

Propyl gallate

Conditions
ConditionsYield
With brominated modified sulfonic acid resin at 100℃; for 5h;98%
With toluene-4-sulfonic acid at 107℃; under 9308.91 Torr; for 0.133333h; Temperature; Wavelength; Sealed tube; Microwave irradiation;94%
With thionyl chloride at 35 - 65℃; for 1h;91.6%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

butan-1-ol
71-36-3

butan-1-ol

Propyl gallate
121-79-9

Propyl gallate

Conditions
ConditionsYield
With sulfuric acid In propan-1-ol; 2-methyl-propan-1-ol; water75%
propan-1-ol
71-23-8

propan-1-ol

methyl galloate
99-24-1

methyl galloate

A

Propyl gallate
121-79-9

Propyl gallate

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With tannase from Lactobacillus plantarum immobilised on glyoxyl-agarose at 25℃; pH=5; aq. acetate buffer; Enzymatic reaction;A 55%
B n/a
propan-1-ol
71-23-8

propan-1-ol

3,4,5-trihydroxybenzoate

3,4,5-trihydroxybenzoate

Propyl gallate
121-79-9

Propyl gallate

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; tannase; phosphoric acid; water at 20 - 35℃; for 24h; Equilibrium constant; Thermodynamic data; ΔrHmo, ΔrGmo, ΔrSmo, other reagents: CH3COONa, CH3COOH; NaOH, 2-(N-morpholino)ethanesulfonic acid; various pH, other reaction time;
propan-1-ol
71-23-8

propan-1-ol

1,3,6-tri-O-galloyl-β-D-glucose
18483-17-5, 23140-70-7, 135029-93-5

1,3,6-tri-O-galloyl-β-D-glucose

A

Propyl gallate
121-79-9

Propyl gallate

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With tannase from Lactobacillus plantarum immobilised on glyoxyl-agarose at 25℃; pH=5; aq. acetate buffer; Enzymatic reaction;
propan-1-ol
71-23-8

propan-1-ol

tannic acid
5424-20-4

tannic acid

Propyl gallate
121-79-9

Propyl gallate

Conditions
ConditionsYield
With bio-imprinted tannase immobilized on ceolite In hexane; water at 40℃; for 24h; Enzymatic reaction;
With tannase from Aspergillus oryzae In hexane; water at 40℃; Kinetics; Microbiological reaction; Enzymatic reaction;
Stage #1: tannic acid With Aspergillus oryzae tannase at 20℃; for 0.0833333h; pH=6.0;
Stage #2: propan-1-ol With D-Mannose; magnesium sulfate In hexane at 40℃; for 24h; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;
With immobilized tannase In hexane; water at 40℃; for 24h; Solvent;
propan-1-ol
71-23-8

propan-1-ol

tannic acid

tannic acid

Propyl gallate
121-79-9

Propyl gallate

Conditions
ConditionsYield
With Aspergillus fumigatus CAS-21 tannase In aq. buffer at 30℃; pH=6; Enzymatic reaction;
Propyl gallate
121-79-9

Propyl gallate

methyl iodide
74-88-4

methyl iodide

3,4,5-trimethoxybenzoic acid propyl ester
6178-45-6

3,4,5-trimethoxybenzoic acid propyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone for 48h; Williamson ether synthesis; Reflux;100%
Propyl gallate
121-79-9

Propyl gallate

benzyl chloride
100-44-7

benzyl chloride

propyl 3,4,5-tris(benzyloxy)benzoate

propyl 3,4,5-tris(benzyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 5h;99%
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux;73%
Propyl gallate
121-79-9

Propyl gallate

3-(perfluorooctyl)propyl iodide
200112-75-0

3-(perfluorooctyl)propyl iodide

propyl 3,4,5-tris(1H,1H,2H,2H,3H,3H-perfluoroundecan-1-yloxy)benzoate

propyl 3,4,5-tris(1H,1H,2H,2H,3H,3H-perfluoroundecan-1-yloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In acetone Inert atmosphere; Reflux;98%
methyl hydrogen fumarate
2756-87-8

methyl hydrogen fumarate

Propyl gallate
121-79-9

Propyl gallate

C15H16O8

C15H16O8

Conditions
ConditionsYield
With sulfuric acid In toluene for 5h; Reflux;98%
Propyl gallate
121-79-9

Propyl gallate

2,2,2-trichloroethoxysulfuryl 2-methyl-3-methylimidazolium triflate
1185733-70-3

2,2,2-trichloroethoxysulfuryl 2-methyl-3-methylimidazolium triflate

C16H15Cl9O14S3
1313434-35-3

C16H15Cl9O14S3

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.266667h;96%
Propyl gallate
121-79-9

Propyl gallate

1-Bromooctadecane
112-89-0

1-Bromooctadecane

propyl 3,4,5-tris(octadecyloxy)benzoate
1167983-67-6

propyl 3,4,5-tris(octadecyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In tetrahydrofuran; acetonitrile at 85℃; for 6h;93%
With potassium carbonate
Propyl gallate
121-79-9

Propyl gallate

<2H9>trimethylsulphoxonium iodide
23726-00-3

<2H9>trimethylsulphoxonium iodide

propyl 3,4,5-tris(methoxy-d3)benzoate

propyl 3,4,5-tris(methoxy-d3)benzoate

Conditions
ConditionsYield
With potassium carbonate at 65℃; for 18h; Sealed tube;92.1%
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

Propyl gallate
121-79-9

Propyl gallate

C20H20BO10*Na(1+)

C20H20BO10*Na(1+)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;92%
1-Bromotetradecane
112-71-0

1-Bromotetradecane

Propyl gallate
121-79-9

Propyl gallate

3,4,5-tristetradecyloxybenzoic acid propyl ester
402912-75-8

3,4,5-tristetradecyloxybenzoic acid propyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 4h; Reflux;90%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;80%
With potassium carbonate In acetone for 48h; Williamson ether synthesis; Reflux;69%
With potassium carbonate In dimethyl sulfoxide; acetone for 10h; Heating;
With potassium carbonate In N,N-dimethyl-formamide at 90℃;
octanol
111-87-5

octanol

Propyl gallate
121-79-9

Propyl gallate

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In 5,5-dimethyl-1,3-cyclohexadiene Reflux;89.9%
Propyl gallate
121-79-9

Propyl gallate

N-(hydroxymethyl)acetamide
625-51-4

N-(hydroxymethyl)acetamide

C13H17NO6

C13H17NO6

Conditions
ConditionsYield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;89.68%
Propyl gallate
121-79-9

Propyl gallate

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

C14H17NO6

C14H17NO6

Conditions
ConditionsYield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;85.92%
Propyl gallate
121-79-9

Propyl gallate

1-dodecylbromide
143-15-7

1-dodecylbromide

propyl 3,4,5-tris(n-dodecan-1-yloxy)benzoate
1228276-91-2

propyl 3,4,5-tris(n-dodecan-1-yloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 20h; Williamson Ether Synthesis;84%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;80%
With potassium carbonate
With potassium carbonate In N,N-dimethyl-formamide at 90℃;
Propyl gallate
121-79-9

Propyl gallate

methyl iodide
74-88-4

methyl iodide

4-methoxypropylgallate

4-methoxypropylgallate

Conditions
ConditionsYield
Stage #1: Propyl gallate With lithium carbonate In N,N-dimethyl-formamide at 50℃; for 0.5h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide Inert atmosphere;
83%
Ru(bis(diphenylphosphino)methane)2Cl2

Ru(bis(diphenylphosphino)methane)2Cl2

Propyl gallate
121-79-9

Propyl gallate

[Ru(propyl 3,4,5-trihydroxybenzoate)(1,1-bis(diphenylphosphino)methane)2]

[Ru(propyl 3,4,5-trihydroxybenzoate)(1,1-bis(diphenylphosphino)methane)2]

Conditions
ConditionsYield
With triethylamine In dichloromethane for 24h; Inert atmosphere;83%
1-iodo-10-undecene
7766-49-6

1-iodo-10-undecene

Propyl gallate
121-79-9

Propyl gallate

3,4,5-tris(10-undecenyloxy)benzoic acid n-propyl ester
894104-86-0

3,4,5-tris(10-undecenyloxy)benzoic acid n-propyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 48h; Heating;82%
Propyl gallate
121-79-9

Propyl gallate

ellagic acid
476-66-4

ellagic acid

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In sulfuric acid at 80℃; for 12h; Solvent; Reagent/catalyst;82%
triethyl borate
150-46-9

triethyl borate

Propyl gallate
121-79-9

Propyl gallate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

Propyl 3-[(4-methyl-phenyl)-sulfonyloxy]-4,5-dihydroxy benzoate
143259-85-2

Propyl 3-[(4-methyl-phenyl)-sulfonyloxy]-4,5-dihydroxy benzoate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; dichloromethane81.7%
Propyl gallate
121-79-9

Propyl gallate

hexadecanyl bromide
112-82-3

hexadecanyl bromide

C58H108O5
1228276-92-3

C58H108O5

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;79%
With potassium carbonate In N,N-dimethyl-formamide at 90℃;
Propyl gallate
121-79-9

Propyl gallate

benzyl bromide
100-39-0

benzyl bromide

4-benzyloxy-3,5-dihydroxy-benzoic acid propyl ester

4-benzyloxy-3,5-dihydroxy-benzoic acid propyl ester

Conditions
ConditionsYield
With potassium hydrogencarbonate In acetonitrile at 20℃; for 16h; Inert atmosphere; Cooling with ice;73.1%
Propyl gallate
121-79-9

Propyl gallate

glycerol
56-81-5

glycerol

1-O-Galloylglycerol
59634-75-2, 87087-60-3

1-O-Galloylglycerol

Conditions
ConditionsYield
With lipozyme 435 at 55℃; for 120h; Temperature; Enzymatic reaction;69.1%
With recombinantlipase B from C. antarctica, expressed in Aspergillusniger, and immobilized on a macroporous hydrophobic resin In neat (no solvent) at 50℃; for 120h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time; Green chemistry; Enzymatic reaction;67.1%
cis-dichlorobis(triphenylphosphine)platinum(II)
10199-34-5, 14056-88-3, 15604-36-1

cis-dichlorobis(triphenylphosphine)platinum(II)

Propyl gallate
121-79-9

Propyl gallate

[Pt(propyl 3,4,5-trihydroxybenzoate)(triphenylphosphine)2]

[Pt(propyl 3,4,5-trihydroxybenzoate)(triphenylphosphine)2]

Conditions
ConditionsYield
With triethylamine In methanol for 24h; Reflux; Inert atmosphere;67%
Propyl gallate
121-79-9

Propyl gallate

2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate
62921-74-8

2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate

C31H54O14

C31H54O14

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In butanone for 26h; Reflux; Inert atmosphere;65.8%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

Propyl gallate
121-79-9

Propyl gallate

diphenyltin(IV) dichloride
1135-99-5

diphenyltin(IV) dichloride

C34H28N2O5Sn

C34H28N2O5Sn

Conditions
ConditionsYield
Stage #1: Propyl gallate; diphenyltin(IV) dichloride In methanol at 20℃; for 4h;
Stage #2: 1,10-Phenanthroline In methanol at 80℃; for 4h;
58%
bromoundecane
693-67-4

bromoundecane

Propyl gallate
121-79-9

Propyl gallate

propyl 3,4,5-tris(undecyloxy)benzoate
1238341-42-8

propyl 3,4,5-tris(undecyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone for 72h; Inert atmosphere; Reflux;50%
2-Chloro-N-(hydroxymethyl)acetamide
2832-19-1

2-Chloro-N-(hydroxymethyl)acetamide

Propyl gallate
121-79-9

Propyl gallate

C13H16ClNO6

C13H16ClNO6

Conditions
ConditionsYield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;43.18%

121-79-9Related news

Application of Propyl gallate (cas 121-79-9) alleviates pericarp browning in harvested longan fruit by modulating metabolisms of respiration and energy09/07/2019

Effects of propyl gallate on metabolisms of respiration and energy of harvested ‘Fuyan’ longans and its relationship to pericarp browning were investigated. Compared to control longans, propyl gallate could reduce ascorbic acid oxidase (AAO) activity, lower cytochrome C oxidase (CCO) activity ...detailed

Propyl gallate (cas 121-79-9) induces cell death and inhibits invasion of human trophoblasts by blocking the AKT and mitogen-activated protein kinase pathways09/06/2019

Propyl gallate (PG) is an antioxidant widely used in food additives, cosmetics, adhesives, and lubricants. PG protects the oils in food products from reacting with hydrogen peroxide and oxygen free radicals, thus preventing spoilage. It is known to have both protective and cytotoxic effects on v...detailed

Adsorption mechanism of Propyl gallate (cas 121-79-9) as a flotation collector on scheelite: A combined experimental and computational study09/05/2019

In this study, propyl gallate (propyl 3,4,5-trihydroxybenzoate; PG) was introduced as a collector for scheelite. The adsorption mechanism on the scheelite surface was investigated by computational and experimental methods, including first principle calculations and Fourier transform infrared (FT...detailed

121-79-9Relevant articles and documents

Characterization of Aspergillus fumigatus CAS-21 tannase with potential for propyl gallate synthesis and treatment of tannery effluent from leather industry

Cavalcanti, Rayza Morganna Farias,Jorge, Jo?o Atílio,Guimar?es, Luis Henrique Souza

, (2018)

One of the tannase isoforms produced by the fungus Aspergillus fumigatus CAS-21 under submerged fermentation (SbmF) was purified 4.9-fold with a 10.2% recovery. The glycoprotein (39.1% carbohydrate content) showed an estimated molecular mass of 60?kDa. Optimum temperature and pH for its activity were 30–40?°C and 5.0, respectively. It showed a half-life (t50) of 60?min at 45 and 50?°C, and it was stable at pH 5.0 and 6.0 for 3?h. The tannase activity was insensitive to most salts used, but it reduced in the presence of Fe2(SO4)3 and FeCl3. On contrary, in presence of SDS, Triton-X100, and urea the enzyme activity increased. The Km value indicated high affinity for propyl gallate (3.61?mmol L?1) when compared with tannic acid (6.38?mmol L?1) and methyl gallate (6.28?mmol L?1), but the best Kcat (362.24?s?1) and Kcat/Km (56.78?s?1 mmol?1 L) were obtained for tannic acid. The purified tannase reduced 89 and 25% of tannin content of the leather tannery effluent generated by manual and mechanical processing, respectively, after 2-h treatment. The total phenolic content was also reduced. Additionally, the enzyme produced propyl gallate, indicating its ability to do the transesterification reaction. Thus, A. fumigatus CAS-21 tannase presents interesting properties, especially the ability to degrade tannery effluent, highlighting its potential in biotechnological applications.

Enhancement of transesterification-catalyzing capability of bio-imprinted tannase in organic solvents by cryogenic protection and immobilization

Nie, Guangjun,Chen, Zhen,Zheng, Zhiming,Jin, Wei,Gong, Guohong,Wang, Li,Yue, Wenjin

, p. 1 - 6 (2013)

Improvement of transesterification-catalyzing capability of bio-imprinted tannase is a crucial question of whether to be efficiently utilized in organic media. As for biotransformation of tannic acid to propyl gallate, bio-imprinting technique can dramatically enhance the transesterification-catalyzing capability of tannase. In this work, both cryogenic protection and immobilization were utilized to further improve its apparent catalytic capability in organic media. The results show that Triton-X-100, mannose, and magnesium ion all have a positive effect on cryogenic protection of the tannase. Particularly, combinational application of the three cryoprotectants increases its catalytic performance by 2.7-fold factor. Also, immobilization further elevates its catalytic capability by 2.1 folds. Noteworthily, the coupling application of immobilization and cryo-protection can cause the conversion rate of substrate of the bio-imprinted tannase to increase to a promising 70%. Consequently, it will be helpful to fully utilize tannase in organic phase.

Self-assembled tetramethyl cucurbit[6]uril-polyoxometalate nanocubes as efficient and recyclable catalysts for the preparation of propyl gallate

Li, Shuang,Xia, Wen,Zhang, Yunqian,Tao, Zhu

, p. 11895 - 11900 (2020)

The development of cucurbit[n]urils-polyoxometalate (Q[n]-POM) hybrids with the same microshape and nanoscale features is highly desirable, yet remains a great challenge. Herein, we design and synthesize a class of Q[n]-POM hybrids and tetramethyl cucurbit[6]uril-phosphomolybdic acid (TMeQ[6]-PMA) nanocubes (NCs) via a facile one-step self-assembly method, as heterogeneous acid catalysts for greatly boosting the catalysts in term of activity and stability for the esterification of gallic acid and n-propanol to propyl gallate (PG). The Fourier transform infrared (FTIR) spectroscopy reveals that the self-assembled mechanism of TMeQ[6]-PMA NCs based on the outer-surface interaction of Q[n]s. The temperature programmed desorption experiments with ammonia and FTIR analysis of the pre-adsorbed pyridine results confirm that the coexistence of medium and strong acid sites and a larger number of Lewis acid sites other than Br?nsted acidic sites on the catalyst surface. These new features make the as-prepared TMeQ[6]-PMA NCs exhibit a high PG conversion (95.6percent) and excellent stability, which epresents a better catalytic performance than other reported catalysts.

Synthesis of propyl gallate from tannic acid catalyzed by tannase from Aspergillus oryzae: Process optimization of transesterification in anhydrous media

Nie, Guangjun,Liu, Hui,Chen, Zhen,Wang, Peng,Zhao, Genhai,Zheng, Zhiming

, p. 102 - 108 (2012)

Improving the catalytic capability of enzyme is an important challenge of biocatalysis in organic medium. Optimization of organic reaction system and reaction mode can elevate the catalytic ability. In order to enhance the catalytic efficiency of tannase-catalyzed transesterification from tannic acid, process parameters of the reaction and reaction mode were optimized further to improve the conversion rate of substrate. The result showed that with hexane as solvent, a conversion rate of substrate, 75%, was achieved at 40 °C in 20 mL reaction mixture composed of 0.75% water and 7.5% n-propanol, and that semicontinuous catalysis was the most favorable for production of propyl gallate, its average production rate was 2.5-fold that of batch catalysis. By SCC, a noted computative conversion rate of approximate, 90%, was obtained. Thus, it is expected that this study may present an efficient and ecofriendly method for industrial production of PG.

Potentiation of vasoconstrictor response and inhibition of endothelium-dependent vasorelaxation by gallic acid in rat aorta

Sanae, Fujiko,Miyaichi, Yukinori,Hayashi, Hisao

, p. 690 - 693 (2002)

In the isolated rat thoracic aorta, gallic acid potentiated the vasoconstrictor response to phenylephrine. The potentiation produced by gallic acid was absent in endothelium-denuded arteries. The potentiation was abolished by NG-nitro-L-arginine methyl ester, an inhibitor of nitric oxide synthesis, and slightly attenuated by an addition of L-arginine, while indomethacin or BQ610 had no effect. The potentiation of response to phenylephrine was not found for structural modifications of gallic acid, except for caffeic acid. Gallic acid also inhibited vasorelaxation induced by acetylcholine, sodium nitroprusside or prostacyclin, especially that by acetylcholine. The effect on vasorelaxation induced by acetylcholine was decreased by esterification of the carboxy group of gallic acid, and in the absence or by the methylation of the o-dihydroxy group. Caffeic acid inhibited the vasorelaxation, though the effect was smaller than that of gallic acid. These findings indicate that gallic acid produces a potentiation of contractile response and inhibition of vasorelaxant responses, probably through inactivation of nitric oxide (NO), in which endothelially produced NO is principally involved, and that the modification of functional groups of the gallic acid molecule abolishes the potentiation of contractile response and attenuates the inhibition of vasorelaxant responses.

Synthesis of propyl gallate by transesterification of tannic acid in aqueous media catalysed by immobilised derivatives of tannase from Lactobacillus plantarum

Fernandez-Lorente, Gloria,Bolivar, Juan Manuel,Rocha-Martin, Javier,Curiel, Jose A.,Mu?oz, Rosario,De Las Rivas, Blanca,Carrascosa, Alfonso V.,Guisan, Jose M.

, p. 214 - 217 (2011)

Immobilised derivatives of tannase from Lactobacillus plantarum were able to catalyse the transesterification of tannic acid by using moderate concentrations of 1-propanol in aqueous media. Transesterification of tannic acid was very similar to transesterification of methyl gallate. The synthetic yield depended on the pH and concentration of 1-propanol, although it did not vary much when using 30% or 50% 1-propanol. Synthetic yields of 45% were obtained with 30% of 1-propanol at pH 5.0. The product was chromatographically pure, and the reaction by-product was 55% pure gallic acid. On the other hand, immobilised tannase was fairly stable under optimal reaction conditions.

Polyhydroxybenzoic acid derivatives as potential new antimalarial agents

Degotte, Gilles,Francotte, Pierre,Pirotte, Bernard,Frédérich, Michel

, (2021/08/07)

With more than 200 million cases and 400,000 related deaths, malaria remains one of the deadliest infectious diseases of 2021. Unfortunately, despite the availability of efficient treatments, we have observed an increase in people infected with malaria since 2015 (from 211 million in 2015 to 229 million in 2019). This trend could partially be due to the development of resistance to all the current drugs. Therefore, there is an urgent need for new alternatives. We have, thus, selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect. Only gallic acid derivatives showed a noticeable potential for further developments. Indeed, they showed a selective inhibitory effect on Plasmodium (IC50 ~20 μM, SI > 5) often associated with interesting water solubility. Moreover, this has confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect. Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) has, for the first time, been recognized as a potential lead for future research because of its marked inhibitory activity against Plasmodium falciparum and its significant hydrosolubility (3.72 mM).

Method of preparing high-purity propyl gallate by stepwise catalysis

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Paragraph 0033-0072, (2019/03/31)

The invention provides a method of preparing high-purity propyl gallate by stepwise catalysis. The method comprises the step of subjecting gallic acid and n-propanol as raw materials to reaction underthe catalytic action of perchloric acid and sulfamic acid or under the catalytic action of p-toluenesulfonic acid and sulfamic acid to obtain propyl gallate. Testing shows that propyl gallate synthesized via the method meets the quality requirements in pharmacopoeia 2015 version, and is up to 99.9% and above in purity, with no gallic acid impurity peak detected.

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