Dodecyl Gallate
(Synonyms: 没食子酸月桂酯,Lauryl gallate) 目录号 : GC47258
A derivative of gallic acid with diverse biological activities
Cas No.:1166-52-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Dodecyl gallate is a derivative of the antioxidant gallic acid that has diverse biological activities, including antioxidant, antiproliferative, and antibacterial properties.1,2,3 It inhibits proliferation of a variety of cancer cells, including WEHI-231 mouse B cell lymphoma, Daudi human lymphoma, and HT-29 human colon cancer cells (IC50s = 0.8, 1.4, and 17.0 µM, respectively).1 It induces apoptosis of WEHI-231 cells but not L-929 mouse fibroblasts. Dodecyl gallate decreases peroxidation of ox brain phospholipid liposomes by 71 and 76% when used at concentrations of 12 and 50 µM, respectively, and scavenges trichloromethyl peroxyl radicals at 0.05% w/v.2 It is active against a variety of Gram-positive bacteria, including B. subtilis (MIC = 25 µg/ml), as well as M. luteus, S. aureus, and methicillin-resistant S. aureus (MRSA; MICs = 12.5 µg/ml for all), and acts by inhibiting the bacterial membrane respiratory chain.3
1.Serrano, A., Palacios, C., Roy, G., et al.Derivatives of gallic acid induce apoptosis in tumoral cell lines and inhibit lymphocyte proliferationArch. Biochem. Biophys.350(1)49-54(1998) 2.Aruoma, O.I., Murcia, A., Butler, J., et al.Evaluation of the antioxidant and prooxidant actions of gallic acid and its derivativesJ. Agric. Food Chem.41(11)1880-1885(1993) 3.Kubo, I., Fujita, K.-i., Nihei, K.-i., et al.Non-antibiotic antibacterial activity of dodecyl gallateBioorg. Med. Chem.11(4)573-580(2003)
| Cas No. | 1166-52-5 | SDF | |
| 别名 | 没食子酸月桂酯,Lauryl gallate | ||
| Canonical SMILES | O=C(C1=CC(O)=C(C(O)=C1)O)OCCCCCCCCCCCC | ||
| 分子式 | C19H30O5 | 分子量 | 338.4 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,Ethanol:PBS (pH 7.2) (1:2): 0.3 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.9551 mL | 14.7754 mL | 29.5508 mL |
| 5 mM | 0.591 mL | 2.9551 mL | 5.9102 mL |
| 10 mM | 0.2955 mL | 1.4775 mL | 2.9551 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
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.PMID:1395563DOI:10.1111/j.1600-0536.1992.tb00238.x.
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 procedure, the results showed that all gallates are moderate to strong contact sensitizers: dodecyl (= lauryl) gallate was found to be the strongest. A characteristic correlation between side chain length and mean response was observed, giving a maximum of sensitization at a length of 12 carbon atoms (Dodecyl Gallate). A literature review revealed that the frequency of reports of allergic contact dermatitis from antioxidants of the gallate type has increased in the last 4 years. In most cases, the moderate sensitizer propyl gallate was the source of sensitization.
Antioxidant activity of Dodecyl Gallate
J Agric Food Chem 2002 Jun 5;50(12):3533-9.PMID:12033824DOI:10.1021/jf011250h.
Dodecyl (C12) gallate exhibits both potent chain-breaking and preventive antioxidant activity. The pyrogallol moiety is responsible for both activities. Dodecyl (lauryl) gallate prevents generation of superoxide radicals by xanthine oxidase, and this activity comes from its ability to inhibit the enzyme. The inhibition kinetics analyzed by Lineweaver-Burk plots found that dodecylgallate is a noncompetitive inhibitor for the generation of superoxide anion. Dodecyl Gallate also inhibits formation of uric acid. The inhibition kinetics analyzed by Lineweaver-Burk plots found that Dodecyl Gallate is a competitive inhibitor for this oxidation. Mitochondrial lipid peroxidation induced by Fe(III)-adenosine 5'-diphosphate/reduced nicotinamide adenine dinucleotide was inhibited by Dodecyl Gallate while its parent compound, gallic acid, did not show this inhibitory activity. Dodecyl Gallate protected mitochondrial functions and human red blood cells against oxidative stresses, but gallic acid showed little effect. The hydrophobic dodecyl group is largely associated with the preventive antioxidative activity.
Dodecyl Gallate, permitted in food, is a strong sensitizer
Contact Dermatitis 1987 May;16(5):260-2.PMID:2957151DOI:10.1111/j.1600-0536.1987.tb01449.x.
Additives are now an established part of our packaged food. Some, like colouring agents and flavouring compounds are hardly necessary or even redundant. Others, mainly antimicrobials and antioxidants, are very important. Antioxidants are not only added to food, but also to cosmetics, pharmaceuticals and industrial products. Dodecyl Gallate belongs with propyl- and octyl-gallate to the synthetic esters of gallic acid. These lipid-soluble phenols are very effective antioxidants. We found contact allergy in 4 of 10 workers having only limited contact with Dodecyl Gallate in the very low concentration of 0.05%. It is important to recognize its strong sensitizing capacity. Workers working with Dodecyl Gallate should avoid direct skin contact.
Wear Analysis of Tibial Inserts Made of Highly Cross-Linked Polyethylene Supplemented with Dodecyl Gallate before and after Accelerated Aging
Polymers (Basel) 2022 Dec 3;14(23):5281.PMID:36501675DOI:10.3390/polym14235281.
The wear of the tibial insert is one of the primary factors leading to the failure of total knee arthroplasty. As materials age, their wear performance often degrades. Supplementing highly cross-linked polyethylene (HXLPE) with Dodecyl Gallate (DG) can improve the oxidation stability of tibial inserts for use in total knee arthroplasty (TKA). This study aimed to evaluate the wear resistance of HXLPE supplemented with DG (HXLPE-DG) tibial inserts before and after accelerated aging. HXLPE-DG tibial inserts were subjected to wear testing of up to 5 million loading cycles according to ISO 14243, and the resulting wear particles were analyzed according to ISO 17853. The wear rate, number, size, and shape of the wear particles were analyzed. The average wear rate of the unaged samples was 4.39 ± 0.75 mg/million cycles and was 3.22 ± 1.49 mg/million cycles for the aged samples. The unaged tibial inserts generated about 2.80 × 107 particles/mL following the wear test, but this was considerably lower for the aged samples at about 1.35 × 107 particles/mL. The average equivalent circle diameter (ECD) of the wear particles from the unaged samples was 0.13 μm (max: 0.80 μm; min: 0.04 μm), and it was 0.14 μm (max: 0.66 μm; min: 0.06 μm) from the aged samples. Moreover, 22.1% of the wear particles from the unaged samples had an aspect ratio (AR) of >4 (slender shape), while this was 15.4% for the aged samples. HXLPE-DG improves the wear performance of the material over time. HXLPE-DG is a novel material that has been demonstrated to have antiaging properties and high wear resistance, making it a promising candidate for use in TKA. Nevertheless, the results are preliminary and will be clarified in further studies.
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.PMID:26707422DOI:10.3892/mmr.2015.4717.
Dodecyl Gallate (DG) is a gallic acid ester that has been shown to inhibit tumor growth. The aim of this study was to investigate the mechanism by which DG induces antiproliferative and apoptotic effects in MG-63 human osteosarcoma cells. Dose- and time-dependent cytotoxic effects of DG were determined using an MTT assay. The results showed that the half-maximal inhibitory concentration (IC50) of DG in MG-63 cells was 31.15 µM at 24 h, 10.66 µM at 48 h, and 9.06 µM at 72 h. Flow cytometric analysis demonstrated that exposure to 20 and 40 µM DG resulted in an increase in the sub-G1 phase population and in S-phase cell cycle arrest. Furthermore, western blot analysis of apoptosis-related protein expression revealed an increase in the activation of caspases 8 and 3, cleavage of poly (ADPribose) polymerase (PARP), and disruption of mitochondrial membrane permeability was measured by flow cytometry. An increase in the Bax/Bcl-2 ratio and a decrease in the expression of inhibitor of apoptosis protein (IAP) family members, namely X-linked inhibitor of apoptosis protein and survivin, were also observed following DG treatment. These data provide insight into the molecular mechanisms governing the ability of DG to induce apoptosis in human osteosarcoma cells in vitro.