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MedKoo Cat#: 598465 | Name: Lauryl gallate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lauryl gallate is the ester of dodecanol and gallic acid. As a food additive it is used under the E number E312 as an antioxidant and preservative.

Chemical Structure

Lauryl gallate
Lauryl gallate
CAS#1166-52-5

Theoretical Analysis

MedKoo Cat#: 598465

Name: Lauryl gallate

CAS#: 1166-52-5

Chemical Formula: C19H30O5

Exact Mass: 338.2093

Molecular Weight: 338.44

Elemental Analysis: C, 67.43; H, 8.94; O, 23.64

Price and Availability

Size Price Availability Quantity
25g USD 250.00 2 Weeks
100g USD 550.00 2 Weeks
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Related CAS #
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Synonym
Lauryl gallate; Nipagallin LA; Progallin LA; NSC 133463; NSC-133463; NSC133463;
IUPAC/Chemical Name
dodecyl 3,4,5-trihydroxybenzoate
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
SMILES Code
O=C(OCCCCCCCCCCCC)C1=CC(O)=C(O)C(O)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Dodecyl gallate (Lauryl gallate) has been widely used as an antioxidant in food manufacturing, as well as in the pharmaceutical and cosmetic industries.
In vitro activity:
The results confirm the antiviral action in cultured cells of LG (lauryl gallate) against African swine fever virus (ASFV), foot and mouth disease virus (FMDV), vesicular stomatitis virus (VSV), and swine vesicular disease virus (SVDV), as well as the inhibitory effect of VPA and CRL on ASFV infection. Reference: Front Microbiol. 2019 Aug 14;10:1853. https://pubmed.ncbi.nlm.nih.gov/31474954/
In vivo activity:
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. Reference: Br J Cancer. 2003 Mar 24;88(6):940-3. https://pubmed.ncbi.nlm.nih.gov/12644834/
Solvent mg/mL mM
Solubility
DMF 30.0 88.64
DMSO 140.0 413.66
Ethanol 30.0 88.64
Ethanol:PBS (pH 7.2) (1:2) 0.3 0.89
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 338.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. de León P, Bustos MJ, Torres E, Cañas-Arranz R, Sobrino F, Carrascosa AL. Inhibition of Porcine Viruses by Different Cell-Targeted Antiviral Drugs. Front Microbiol. 2019 Aug 14;10:1853. doi: 10.3389/fmicb.2019.01853. PMID: 31474954; PMCID: PMC6702965. 2. Kubo I, Fujita Ki, Nihei Ki, Masuoka N. Non-antibiotic antibacterial activity of dodecyl gallate. Bioorg Med Chem. 2003 Feb 20;11(4):573-80. doi: 10.1016/s0968-0896(02)00436-4. PMID: 12538022. 3. Ortega E, Sadaba MC, Ortiz AI, Cespon C, Rocamora A, Escolano JM, Roy G, Villar LM, Gonzalez-Porque P. Tumoricidal activity of lauryl gallate towards chemically induced skin tumours in mice. Br J Cancer. 2003 Mar 24;88(6):940-3. doi: 10.1038/sj.bjc.6600805. PMID: 12644834; PMCID: PMC2377081.
In vitro protocol:
1. de León P, Bustos MJ, Torres E, Cañas-Arranz R, Sobrino F, Carrascosa AL. Inhibition of Porcine Viruses by Different Cell-Targeted Antiviral Drugs. Front Microbiol. 2019 Aug 14;10:1853. doi: 10.3389/fmicb.2019.01853. PMID: 31474954; PMCID: PMC6702965. 2. Kubo I, Fujita Ki, Nihei Ki, Masuoka N. Non-antibiotic antibacterial activity of dodecyl gallate. Bioorg Med Chem. 2003 Feb 20;11(4):573-80. doi: 10.1016/s0968-0896(02)00436-4. PMID: 12538022.
In vivo protocol:
1. Ortega E, Sadaba MC, Ortiz AI, Cespon C, Rocamora A, Escolano JM, Roy G, Villar LM, Gonzalez-Porque P. Tumoricidal activity of lauryl gallate towards chemically induced skin tumours in mice. Br J Cancer. 2003 Mar 24;88(6):940-3. doi: 10.1038/sj.bjc.6600805. PMID: 12644834; PMCID: PMC2377081.
1: Feuser PE, Arévalo JM, Junior EL, Rossi GR, da Silva Trindade E, Rocha ME, Jacques AV, Ricci-Júnior E, Santos-Silva MC, Sayer C, de Araújo PH. Increased cellular uptake of lauryl gallate loaded in superparamagnetic poly(methyl methacrylate) nanoparticles due to surface modification with folic acid. J Mater Sci Mater Med. 2016 Dec;27(12):185. Epub 2016 Oct 27. PubMed PMID: 27787810. 2: Jurak M, Miñones J Jr. Interactions of lauryl gallate with phospholipid components of biological membranes. Biochim Biophys Acta. 2016 Aug;1858(8):1821-32. doi: 10.1016/j.bbamem.2016.04.012. Epub 2016 Apr 24. PubMed PMID: 27117642. 3: Teng CL, Han SM, Wu WC, Hsueh CM, Tsai JR, Hwang WL, Hsu SL. Mechanistic aspects of lauryl gallate-induced differentiation and apoptosis in human acute myeloid leukemia cells. Food Chem Toxicol. 2014 Sep;71:197-206. doi: 10.1016/j.fct.2014.06.019. Epub 2014 Jun 30. PubMed PMID: 24994563. 4: Jurak M. Effect of Lauryl Gallate on Wetting Properties of Organized Thin Phospholipid Films on Mica. J Phys Chem B. 2016 Jul 14;120(27):6657-66. doi: 10.1021/acs.jpcb.6b02434. Epub 2016 Jun 30. PubMed PMID: 27332889. 5: Reynaud C, Tapin-Lingua S, Elegir G, Petit-Conil M, Baumberger S. Hydrophobic properties conferred to Kraft pulp by a laccase-catalysed treatment with lauryl gallate. J Biotechnol. 2013 Sep 10;167(3):302-8. doi: 10.1016/j.jbiotec.2013.07.014. Epub 2013 Jul 19. PubMed PMID: 23876480. 6: Calcabrini A, García-Martínez JM, González L, Tendero MJ, Ortuño MT, Crateri P, Lopez-Rivas A, Arancia G, González-Porqué P, Martín-Pérez J. Inhibition of proliferation and induction of apoptosis in human breast cancer cells by lauryl gallate. Carcinogenesis. 2006 Aug;27(8):1699-712. Epub 2006 Apr 19. PubMed PMID: 16624827. 7: Hurtado C, Bustos MJ, Sabina P, Nogal ML, Granja AG, González ME, Gónzalez-Porqué P, Revilla Y, Carrascosa AL. Antiviral activity of lauryl gallate against animal viruses. Antivir Ther. 2008;13(7):909-17. PubMed PMID: 19043925. 8: Roy G, Lombardía M, Palacios C, Serrano A, Cespón C, Ortega E, Eiras P, Lujan S, Revilla Y, Gonzalez-Porqué P. Mechanistic aspects of the induction of apoptosis by lauryl gallate in the murine B-cell lymphoma line Wehi 231. Arch Biochem Biophys. 2000 Nov 15;383(2):206-14. PubMed PMID: 11185555. 9: Ortega E, Sadaba MC, Ortiz AI, Cespon C, Rocamora A, Escolano JM, Roy G, Villar LM, Gonzalez-Porque P. Tumoricidal activity of lauryl gallate towards chemically induced skin tumours in mice. Br J Cancer. 2003 Mar 24;88(6):940-3. PubMed PMID: 12644834; PubMed Central PMCID: PMC2377081. 10: Palacios C, Cespón C, Martín De La Vega C, Roy G, Serrano A, Salinas M, González-Porqué P. Lauryl gallate inhibits the activity of protein tyrosine kinase c-Src purified from human platelets. J Enzyme Inhib. 2001 Dec;16(6):527-33. PubMed PMID: 12164392. 11: Cheng CH, Cheng YP, Chang IL, Chen HY, Wu CC, Hsieh CP. Dodecyl gallate induces apoptosis by upregulating the caspase-dependent apoptotic pathway and inhibiting the expression of anti-apoptotic Bcl-2 family proteins in human osteosarcoma cells. Mol Med Rep. 2016 Feb;13(2):1495-500. doi: 10.3892/mmr.2015.4717. Epub 2015 Dec 24. PubMed PMID: 26707422; PubMed Central PMCID: PMC4732860. 12: Gamboni SE, Palmer AM, Nixon RL. Allergic contact stomatitis to dodecyl gallate? A review of the relevance of positive patch test results to gallates. Australas J Dermatol. 2013 Aug;54(3):213-7. doi: 10.1111/j.1440-0960.2012.00941.x. Epub 2012 Sep 4. PubMed PMID: 22943875. 13: Hausen BM, Beyer W. The sensitizing capacity of the antioxidants propyl, octyl, and dodecyl gallate and some related gallic acid esters. Contact Dermatitis. 1992 Apr;26(4):253-8. Review. PubMed PMID: 1395563. 14: Raccagni AA, Frattagli M, Baldari U, Righini MG. Lauryl gallate hand dermatitis in a cheese counter assistant. Contact Dermatitis. 1997 Oct;37(4):182. PubMed PMID: 9385516. 15: Kubo I, Masuoka N, Xiao P, Haraguchi H. Antioxidant activity of dodecyl gallate. J Agric Food Chem. 2002 Jun 5;50(12):3533-9. PubMed PMID: 12033824. 16: Kubo I, Fujita Ki, Nihei Ki, Masuoka N. Non-antibiotic antibacterial activity of dodecyl gallate. Bioorg Med Chem. 2003 Feb 20;11(4):573-80. PubMed PMID: 12538022. 17: Garcia-Ubasart J, Colom JF, Vila C, Gómez Hernández N, Blanca Roncero M, Vidal T. A new procedure for the hydrophobization of cellulose fibre using laccase and a hydrophobic phenolic compound. Bioresour Technol. 2012 May;112:341-4. doi: 10.1016/j.biortech.2012.02.075. Epub 2012 Feb 25. PubMed PMID: 22440576. 18: van der Meeren HL. Dodecyl gallate, permitted in food, is a strong sensitizer. Contact Dermatitis. 1987 May;16(5):260-2. PubMed PMID: 2957151. 19: Fujita K, Kubo I. Plasma membrane injury induced by nonyl gallate in Saccharomyces cerevisiae. J Appl Microbiol. 2002;92(6):1035-42. PubMed PMID: 12010543. 20: Hossain KhM, González MD, Lozano GR, Tzanov T. Multifunctional modification of wool using an enzymatic process in aqueous-organic media. J Biotechnol. 2009 Apr 20;141(1-2):58-63. doi: 10.1016/j.jbiotec.2009.02.011. Epub 2009 Feb 27. PubMed PMID: 19428731.