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121-79-9

Basic Information
CAS No.: 121-79-9
Name: Propyl gallate
Molecular Structure:
Molecular Structure of 121-79-9 (Propyl gallate)
Formula: C10H12O5
Molecular Weight: 212.20
Synonyms: Tenox PG;Nipagallin P;Benzoic acid,3,4,5-trihydroxy-,esters,propyl ester;n-Propyl 3,4,5-trihydroxybenzoate;3,4, 5-Trihydroxybenzoic acid, propyl ester;Benzoic acid, 3,4, 5-trihydroxy-, propyl ester;Progallin P;Propyl 3,4,5-trihydroxybenzoate;n-Propyl ester of 3,4,5-trihydroxybenzoic acid;Nipa 49;Nipanox S 1;Gallic acid, propyl ester;3,4,5-Trihydroxybenzene-1-propylcarboxylate;n-Propyl gallate;Propyl Gallate BP/EP;Propyl Gallate (Tech.);propyl gallate;propyl 3,4,5-trihydroxybenzoate;
EINECS: 204-498-2
Density: 1.363 g/cm3
Melting Point: 146-149 °C(lit.)
Boiling Point: 448.6 °C at 760 mmHg
Flash Point: 181.3 °C
Solubility: ethanol: 50 mg/mL
Appearance: white to light beige crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-43
Safety: 24-37
Transport Information:
PSA: 86.99000
LogP: 1.37020
Synthetic route
71-23-8

propan-1-ol

149-91-7

3,4,5-trihydroxybenzoic acid

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%
149-91-7

3,4,5-trihydroxybenzoic acid

71-36-3

butan-1-ol

121-79-9

Propyl gallate

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

propan-1-ol

99-24-1

methyl galloate

A

121-79-9

Propyl gallate

B

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
71-23-8

propan-1-ol

3,4,5-trihydroxybenzoate

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;
71-23-8

propan-1-ol

18483-17-5, 23140-70-7, 135029-93-5

1,3,6-tri-O-galloyl-β-D-glucose

A

121-79-9

Propyl gallate

B

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;
71-23-8

propan-1-ol

5424-20-4

tannic acid

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;
71-23-8

propan-1-ol

tannic acid

tannic acid

121-79-9

Propyl gallate

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

Propyl gallate

74-88-4

methyl iodide

6178-45-6

3,4,5-trimethoxybenzoic acid propyl ester

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

Propyl gallate

100-44-7

benzyl chloride

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%
121-79-9

Propyl gallate

200112-75-0

3-(perfluorooctyl)propyl iodide

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%
2756-87-8

methyl hydrogen fumarate

121-79-9

Propyl gallate

C15H16O8

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

Propyl gallate

1185733-70-3

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

1313434-35-3

C16H15Cl9O14S3

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

Propyl gallate

112-89-0

1-Bromooctadecane

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
121-79-9

Propyl gallate

23726-00-3

<2H9>trimethylsulphoxonium iodide

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

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

sodium tetrahydroborate

121-79-9

Propyl gallate

C20H20BO10*Na(1+)

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

1-Bromotetradecane

121-79-9

Propyl gallate

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℃;
111-87-5

octanol

121-79-9

Propyl gallate

1034-01-1

Octyl gallate

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

Propyl gallate

625-51-4

N-(hydroxymethyl)acetamide

C13H17NO6

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

Propyl gallate

924-42-5

N-Methylolacrylamid

C14H17NO6

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

Propyl gallate

143-15-7

1-dodecylbromide

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℃;
121-79-9

Propyl gallate

74-88-4

methyl iodide

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

121-79-9

Propyl gallate

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

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

1-iodo-10-undecene

121-79-9

Propyl gallate

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%
121-79-9

Propyl gallate

476-66-4

ellagic acid

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

triethyl borate

121-79-9

Propyl gallate

98-59-9

p-toluenesulfonyl chloride

143259-85-2

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

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

Propyl gallate

112-82-3

hexadecanyl bromide

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℃;
121-79-9

Propyl gallate

100-39-0

benzyl bromide

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%
121-79-9

Propyl gallate

56-81-5

glycerol

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%
10199-34-5, 14056-88-3, 15604-36-1

cis-dichlorobis(triphenylphosphine)platinum(II)

121-79-9

Propyl gallate

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

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

Propyl gallate

62921-74-8

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

C31H54O14

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

1,10-Phenanthroline

121-79-9

Propyl gallate

1135-99-5

diphenyltin(IV) dichloride

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%
693-67-4

bromoundecane

121-79-9

Propyl gallate

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%
2832-19-1

2-Chloro-N-(hydroxymethyl)acetamide

121-79-9

Propyl gallate

C13H16ClNO6

Conditions
ConditionsYield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;43.18%
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    CAS NO:121-79-9 Chemical Name: Propyl 3,4,5-trihydroxybenzoate Structural formula: Molecular formula & Molecular weight:C10H12O5;212.21 Appearance: white to milky white crystalline granules Quality index: in accordance with the nation

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Chemistry

Molecular Structure of Propyl gallate (CAS NO.121-79-9):

IUPAC Name: propyl 3,4,5-trihydroxybenzoate
Molecular Formula: C10H12O5
Formula Weight: 212.2
H bond acceptors: 5
H bond donors: 3
Freely Rotating Bonds: 7
Polar Surface Area: 53.99Å2
Index of Refraction: 1.595
Molar Refractivity: 52.93 cm3
Molar Volume: 155.6 cm3
Surface Tension: 62 dyne/cm
Density: 1.363 g/cm3
Flash Point: 181.3 °C
Enthalpy of Vaporization: 73.43 kJ/mol
Boiling Point: 448.6 °C at 760 mmHg
Vapour Pressure: 1.16E-08 mmHg at 25°C
Melting point: 146-149 °C(lit.)
Storage temp: 0-6°C
Solubility: ethanol: 50 mg/mL
Form: powder
Water Solubility: 0.35 g/100 mL (25 oC)
InChI
InChI=1/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3
Smiles
c1(cc(c(O)c(c1)O)O)C(OCCC)=O

Toxicity Data With Reference

1.    

mmo-sat 200 µg/plate

    SYSWAE    Shiyan Shengwa Xuebao. Journal of Experimental Biology. (Guozi Shudian, China Publications Center, P.O. Box 399, Peking, Peoples Republic of China) V.1- 1953- 12 (1979),41.
2.    

cyt-ham:fbr 40 mg/L

    ESKHA5    Eisei Shikenjo Hokoku. Bulletin of the National Hygiene Sciences. 96 (1978),55.
3.    

orl-rat LD50:2100 mg/kg

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB245-441 .
4.    

ipr-rat LD50:380 mg/kg

    FOTEAO    Food Technology. 2 (1948),308.
5.    

orl-mus LD50:1700 mg/kg

    JAOCA7    Journal of the American Oil Chemists Society. 54 (1977),239.
6.    

orl-cat LD50:400 mg/kg

    14CYAT    Industrial Hygiene and Toxicology. 2 (1963),1897.

Consensus Reports

NTP Carcinogenesis Bioassay (feed); No Evidence: mouse, rat NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-240 ,1982. . Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 22-43-36/37/38 (Harmful if swallowed; May cause sensitization by skin contact; Irritating to the eyes; Irritating to the respiratory system; Irritating to the skin)
Safety Statements: 24-37-36-26 (Avoid contact with skin; Wear suitable gloves; Wear suitable protective clothing; In case of contact with eyes, rinse immediately with plenty of water and seek medical advice)
WGK Germany: 2
RTECS: LW8400000
HS Code: 29182950
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.

Specification

  Propyl gallate , with CAS number of 121-79-9, can be called 3,4,5-Trihydroxybenzene-1-propylcarboxylate ; Propyl Gallate BP/EP ; propyl gallate;propyl 3,4,5-trihydroxybenzoate ; n-Propyl ester of 3,4,5-trihydroxybenzoic acid ; Benzoic acid, 3,4, 5-trihydroxy-, propyl ester ; 3,4, 5-Trihydroxybenzoic acid, propyl ester . It is a white to light beige crystalline powder. Propyl gallate (CAS NO.121-79-9) is used as a triplet quencher in fluorescence microscopy. It is used as food and feed additives, and in foods, cosmetics, hair products, adhesives, and lubricants. n-PROPYL GALLATE is used to protect oils and fats in products from oxidation.