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Lauryl gallate

Alias: Progallin LA; Nipagallin LA; Dodecyl gallate; Lauryl gallate; 1166-52-5; Dodecyl 3,4,5-trihydroxybenzoate; Nipagallin LA; Progallin LA; BENZOIC ACID, 3,4,5-TRIHYDROXY-, DODECYL ESTER; n-Dodecyl gallate; Lauryl gallate
Cat No.:V23803 Purity: ≥98%
Dodecyl gallate (Lauryl gallate) is extensively used as an antioxidant in food manufacturing and the pharmaceutical and cosmetic industries.
Lauryl gallate
Lauryl gallate Chemical Structure CAS No.: 1166-52-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Dodecyl gallate (Lauryl gallate) is extensively used as an antioxidant in food manufacturing and the pharmaceutical and cosmetic industries. Dodecyl gallate is also active against animal viruses, like African swine fever virus (ASFV).
Biological Activity I Assay Protocols (From Reference)
Targets
Antioxidant; Antiviral; food additive; natural product
ln Vitro
Lauryl gallate (lauryl gallate) is a natural plant phenolic chemical that is an ester derivative of gallic acid. Lauryl gallate (lauryl gallate) inhibits lipid peroxidase, increases the expression of antioxidant genes, and scavenges free radicals to shield cells from oxidative stress. Lauryl gallate can cause protein inactivation and damage biofilms because of its hydrophobic properties [1].
ln Vivo
Lauryl gallate (antioxidant food additive E-312) prevents the formation of dimethylbenzanthracene-induced skin tumours in mice, and kills, selectively, tumoral cells on established tumours. This results in total remission, after topical application of the compound on the tumoral mass, without affecting the surrounding tissue.[2]
Animal Protocol
Prevention of tumour formation[2]
Thirty-two IRC mice were individualised and subdivided into four groups (four females and four males per group), as shown in Table 1 . The induction of the tumours was performed following the protocol described (Segal et al, 1978) with a slight modification. The solvent used was a mixture of dimethylsulphoxide and glycerol (1 : 1), in which all the compounds were soluble. After a single application of 25 μg of 7,12-dimethylbenz[a]anthracene (DMBA) in a volume of 20 μl, and 15 days without treatment, a solution of 5 μg of phorbol-12-myristate-13-acetate (PMA) with different doses of lauryl gallate (LG) was applied topically three times per week. The doses of lauryl gallate (LG) were 0 (controls), 2.5, 10 and 50 μg in a volume of 20 μl per application. After 6–7 weeks of treatment, tumours appeared on 90% of the control mice, and the behaviour of lauryl gallate (LG) was evaluated as shown in Table 1.
Regression of established tumours[2]
Twenty-four individualised mice were treated with a single application of 25 μg of DMBA, and after 15 days with no application of compounds, 5 μg of PMA was applied three times a week (6–7 weeks) until the tumour appeared. The mice were subdivided into three different groups (LG 100, LG 250 and LG 500, four males and four females per group), depending on the treatment dose after tumour formation. The volume per application was 20 μl, which was sufficient to cover the whole tumour surface and was applied three times a week for a period of 8 weeks.
Toxicity/Toxicokinetics
rat LD50 oral 5 gm/kg KIDNEY, URETER, AND BLADDER: OTHER CHANGES Voeding., 16(683), 1955
rat LD50 intraperitoneal 100 mg/kg FAO Nutrition Meetings Report Series., 38A(22), 1965
pig LD50 oral >6 gm/kg KIDNEY, URETER, AND BLADDER: OTHER CHANGES Voeding., 16(683), 1955
References

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

[2]. Tumoricidal activity of lauryl gallate towards chemically induced skin tumours in mice. Br J Cancer . 2003 Mar 24;88(6):940-3.

Additional Infomation
Dodecyl gallate is a gallate ester.
Dodecyl gallate has been reported in Alchornea glandulosa with data available.
Dodecyl gallate is an antioxidant used in foods especially oil, fats, cheeses and mashed potato. Dodecyl gallate is a permitted for use in margarine in USA. Possesses same antioxidant effects as propyl gallate but incr. alkyl chain length gives rise to greater fat solubility.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H30O5
Molecular Weight
338.44
Exact Mass
338.209
Elemental Analysis
C, 67.43; H, 8.94; O, 23.64
CAS #
1166-52-5
PubChem CID
14425
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
521.7±45.0 °C at 760 mmHg
Melting Point
94-97 °C(lit.)
Flash Point
180.3±22.2 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.535
LogP
7.38
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
13
Heavy Atom Count
24
Complexity
322
Defined Atom Stereocenter Count
0
InChi Key
RPWFJAMTCNSJKK-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H30O5/c1-2-3-4-5-6-7-8-9-10-11-12-24-19(23)15-13-16(20)18(22)17(21)14-15/h13-14,20-22H,2-12H2,1H3
Chemical Name
dodecyl 3,4,5-trihydroxybenzoate
Synonyms
Progallin LA; Nipagallin LA; Dodecyl gallate; Lauryl gallate; 1166-52-5; Dodecyl 3,4,5-trihydroxybenzoate; Nipagallin LA; Progallin LA; BENZOIC ACID, 3,4,5-TRIHYDROXY-, DODECYL ESTER; n-Dodecyl gallate; Lauryl gallate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~738.68 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9547 mL 14.7737 mL 29.5473 mL
5 mM 0.5909 mL 2.9547 mL 5.9095 mL
10 mM 0.2955 mL 1.4774 mL 2.9547 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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