Dodecyl gallate

Names

[ Name ]:
Dodecyl gallate

[Synonym ]:
3,4,5-trihydroxy-benzoic acid dodecyl ester
Nipagallin LA
3mg/kg
dodecyl3,4,5
Benzoic acid, 3,4,5-trihydroxy-, dodecyl ester
Dodecyl gallate
E312
MFCD00002195
Lauryl gallate
Gallic acid, lauryl ester
lauryl 3,4,5-trihydroxybenzoate
Dodecyl 3,4,5-trihydroxybenzoate
Gallic acid, dodecyl ester (8CI)
Gallic acid n-dodecyl ester
Gallic Acid Lauryl Ester
n-dodecyl gallate
Progallin LA
Gallic acid, dodecyl ester
Gallic Acid Dodecyl Ester
EINECS 214-620-6

Biological Activity

[Description]:

Dodecyl gallate (Lauryl gallate) has been widely used as an antioxidant in food manufacturing, as well as in the pharmaceutical and cosmetic industries. Dodecyl gallate also is active against a highly relevant animal virus such as African swine fever virus (ASFV)[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Others >> Others

[In Vitro]

Dodecyl gallate (Lauryl gallate) is an ester derivative of gallic acid, a natural plant phenolic compound. Dodecyl gallate (Lauryl gallate) protects cells from oxidative stress, in a process associated with radical scavenging, inhibition of enzymes involved in lipid peroxidation, and increasing expression of antioxidant genes. Due to its hydrophobic properties, Dodecyl gallate can disrupt biomembranes and cause protein inactivation[1].

[References]

[1]. Patricia de León, et al. Inhibition of Porcine Viruses by Different Cell-Targeted Antiviral Drugs. Front Microbiol. 2019 Aug 14;10:1853.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
521.7±45.0 °C at 760 mmHg

[ Melting Point ]:
94-97 °C(lit.)

[ Molecular Formula ]:
C₁₉H₃₀O₅

[ Molecular Weight ]:
338.439

[ Flash Point ]:
180.3±22.2 °C

[ Exact Mass ]:
338.209320

[ PSA ]:
86.99000

[ LogP ]:
7.38

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.535

[ Storage condition ]:
0-6°C

[ Water Solubility ]:
practically insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DH9100000

CHEMICAL NAME :: Benzoic acid, 3,4,5-trihydroxy-, dodecyl ester

CAS REGISTRY NUMBER :: 1166-52-5

BEILSTEIN REFERENCE NO. :: 2701981

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C19-H30-O5

MOLECULAR WEIGHT :: 338.49

WISWESSER LINE NOTATION :: QR BQ CQ EVO12

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FAONAU FAO Nutrition Meetings Report Series. (Rome, Italy) No.?-57, 1948-77. Discontinued. Volume(issue)/page/year: 38A,22,1965 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 135 gm/kg/32W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 28,304,1951

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 75 gm/kg/10D-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Related to Chronic Data - death

REFERENCE :: JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 28,304,1951

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H317

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R43

[ Safety Phrases ]:
S24-S37

[ RIDADR ]:
3335

[ WGK Germany ]:
1

[ RTECS ]:
DH9100000

[ HS Code ]:
29182950

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918290000

[ Summary ]:
HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

Articles

Apolar Radical Initiated Conjugated Autoxidizable Triene (ApoCAT) Assay: Effects of Oxidant Locations on Antioxidant Capacities and Interactions.

J. Agric. Food Chem. 63 , 7546-55, (2015)

Development of an antioxidant assay explaining antioxidant behaviors in complex food systems has been a challenging topic for food scientists. This research aimed to investigate antioxidant capacities...

Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.

Bioorg. Med. Chem. Lett. 19 , 1793-6, (2009)

The antifungal activity of a complete series of 15 n-alkyl gallates and six analogues acting against a representative panel of opportunistic pathogenic fungi was studied in order to analyze their role...

The sensitizing capacity of the antioxidants propyl, octyl, and dodecyl gallate and some related gallic acid esters.

Contact Dermatitis 26(4) , 253-8, (1992)

8 alkyl gallates, including the widely used antioxidants propyl, octyl, and dodecyl (= lauryl) gallate, have been subjected to experimental sensitization in guinea pigs. Using a modern sensitization p...