Gallotannin | CAS#5424-20-4 | Inhibitor

MedKoo Cat#: 112108 | Name: Gallotannin

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Description:

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

Gallotannin has antioxidant, anti-inflammatory, antiviral, and antiproliferative biological activities and inhibits the intracellular production of reactive oxygen species (ROS) and DNA damage induced by phorbol 12-myristate 13-acetate in human polymorphonuclear neutrophils (PMNs). It also inhibits the proliferation of MDA-MB-231 and MCF-7 human breast cancer cells (IC50s = 2.5 and 4 μM, respectively).

Chemical Structure

Gallotannin

CAS#5424-20-4

Theoretical Analysis

MedKoo Cat#: 112108

Name: Gallotannin

CAS#: 5424-20-4

Chemical Formula: C76H52O46

Exact Mass: 1700.1730

Molecular Weight: 1701.21

Elemental Analysis: C, 53.66; H, 3.08; O, 43.26

Price and Availability

Size	Price	Availability	Quantity
10g	USD 250.00	2 Weeks
25g	USD 450.00	2 Weeks

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Related CAS #

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Synonym

Gallotannin; Tannic Acid; Glycerite; Chinese gallotannin; Gallotannic acid

IUPAC/Chemical Name

(2S,3R,4S,5R,6R)-6-(((3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoyl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrakis(3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoate)

InChi Key

LRBQNJMCXXYXIU-PPKXGCFTSA-N

InChi Code

InChI=1S/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2/t52-,63-,64+,65-,76+/m1/s1

SMILES Code

OC1=C(O)C(O)=CC(C(OC2=CC(C(OC[C@@H]3[C@@H](OC(C4=CC(O)=C(O)C(OC(C5=CC(O)=C(O)C(O)=C5)=O)=C4)=O)[C@H](OC(C6=CC(O)=C(O)C(OC(C7=CC(O)=C(O)C(O)=C7)=O)=C6)=O)[C@@H](OC(C8=CC(O)=C(O)C(OC(C9=CC(O)=C(O)C(O)=C9)=O)=C8)=O)[C@H](OC(C%10=CC(O)=C(O)C(OC(C%11=CC(O)=C(O)C(O)=C%11)=O)=C%10)=O)O3)=O)=CC(O)=C2O)=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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	5.88
	PBS (pH:7.2)	0.3	0.18

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 1,701.21 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.

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

1: Barnes RC, Kim H, Fang C, Bennett W, Nemec M, Sirven MA, Suchodolski JS, Deutz N, Britton RA, Mertens-Talcott SU, Talcott ST. Body Mass Index as a Determinant of Systemic Exposure to Gallotannin Metabolites during 6-Week Consumption of Mango (Mangifera indica L.) and Modulation of Intestinal Microbiota in Lean and Obese Individuals. Mol Nutr Food Res. 2019 Jan;63(2):e1800512. doi: 10.1002/mnfr.201800512. Epub 2018 Nov 28. PMID: 30427574. 2: Ryeom GGM, Bang WJ, Kim YB, Lee GE. Gallotannin Improves the Photoaged- Related Proteins by Extracellular Signal-Regulated Kinases/c-Jun N-Terminal Kinases Signaling Pathway in Human Epidermal Keratinocyte Cells. J Med Food. 2018 Aug;21(8):785-792. doi: 10.1089/jmf.2017.4096. Epub 2018 Jul 13. PMID: 30004816. 3: Houssein M, Abi Saab W, Khalil M, Khalife H, Fatfat M. Cell Death by Gallotannin Is Associated with Inhibition of the JAK/STAT Pathway in Human Colon Cancer Cells. Curr Ther Res Clin Exp. 2020 Jun 13;92:100589. doi: 10.1016/j.curtheres.2020.100589. PMID: 32714471; PMCID: PMC7378856. 4: Yue LM, Lee J, Zheng L, Park YD, Ye ZM, Yang JM. Computational prediction integrating the inhibition kinetics of gallotannin on α-glucosidase. Int J Biol Macromol. 2017 Oct;103:829-838. doi: 10.1016/j.ijbiomac.2017.05.106. Epub 2017 May 21. PMID: 28539267. 5: Kang MJ, Kim JE, Park JW, Choi HJ, Bae SJ, Choi SI, Hong JT, Hwang DY. Effects of Gallotannin-Enriched Extract of Galla Rhois on the Activation of Apoptosis, Cell Cycle Arrest, and Inhibition of Migration Ability in LLC1 Cells and LLC1 Tumors. Pathol Oncol Res. 2021 Apr 30;27:588084. doi: 10.3389/pore.2021.588084. PMID: 34257536; PMCID: PMC8262247. 6: Kim J, Yhim WB, Park JW, Lee SH, Kim TY, Cha SH, Kim HS, Jang HL, Cho M, Park Y, Cho S. Gallotannin-Capped Gold Nanoparticles: Green Synthesis and Enhanced Morphology of AFM Images. J Nanosci Nanotechnol. 2016 Jun;16(6):5991-8. doi: 10.1166/jnn.2016.10965. PMID: 27427661. 7: Kwon HY, Kim JH, Kim B, Srivastava SK, Kim SH. Regulation of SIRT1/AMPK axis is critically involved in gallotannin-induced senescence and impaired autophagy leading to cell death in hepatocellular carcinoma cells. Arch Toxicol. 2018 Jan;92(1):241-257. doi: 10.1007/s00204-017-2021-y. Epub 2017 Jul 4. Erratum in: Arch Toxicol. 2018 Sep;92(9):2979. PMID: 28676953. 8: Wei K, He H, Li H, Wang L, Ruan L, Pang D, Cheng H. Gallotannin 1,2,6-tri-O- galloyl-β-d-glucopyranose: Its availability and changing patterns in tea (Camellia sinensis). Food Chem. 2019 Oct 30;296:40-46. doi: 10.1016/j.foodchem.2019.05.144. Epub 2019 May 22. PMID: 31202304. 9: Go J, Kim JE, Koh EK, Song SH, Kang HG, Lee YH, Kim HD, Hong JT, Hwang DY. Hepatoprotective Effect of Gallotannin-enriched Extract Isolated from Gall on Hydrogen Peroxide-induced Cytotoxicity in HepG2 Cells. Pharmacogn Mag. 2017 Jul;13(Suppl 2):S294-S300. doi: 10.4103/pm.pm_424_15. Epub 2017 Jul 11. PMID: 28808395; PMCID: PMC5538169. 10: Kantapan J, Paksee S, Duangya A, Sangthong P, Roytrakul S, Krobthong S, Suttana W, Dechsupa N. A radiosensitizer, gallotannin-rich extract from Bouea macrophylla seeds, inhibits radiation-induced epithelial-mesenchymal transition in breast cancer cells. BMC Complement Med Ther. 2021 Jul 3;21(1):189. doi: 10.1186/s12906-021-03363-6. PMID: 34217266; PMCID: PMC8254241. 11: Mun JG, Han YH, Jeon HD, Yoon DH, Lee YG, Hong SH, Kee JY. Inhibitory Effect of Gallotannin on Lung Metastasis of Metastatic Colorectal Cancer Cells by Inducing Apoptosis, Cell Cycle Arrest and Autophagy. Am J Chin Med. 2021;49(6):1535-1555. doi: 10.1142/S0192415X21500725. Epub 2021 Jul 10. PMID: 34247563. 12: Niemetz R, Gross GG. Enzymology of gallotannin and ellagitannin biosynthesis. Phytochemistry. 2005 Sep;66(17):2001-11. doi: 10.1016/j.phytochem.2005.01.009. PMID: 16153405. 13: A Youness R, Kamel R, A Elkasabgy N, Shao P, A Farag M. Recent Advances in Tannic Acid (Gallotannin) Anticancer Activities and Drug Delivery Systems for Efficacy Improvement; A Comprehensive Review. Molecules. 2021 Mar 9;26(5):1486. doi: 10.3390/molecules26051486. PMID: 33803294; PMCID: PMC7967207. 14: Han HJ, Kwon HY, Sohn EJ, Ko H, Kim B, Jung K, Lew JH, Kim SH. Suppression of E-cadherin mediates gallotannin induced apoptosis in Hep G2 hepatocelluar carcinoma cells. Int J Biol Sci. 2014 Apr 25;10(5):490-9. doi: 10.7150/ijbs.7495. PMID: 24795530; PMCID: PMC4007362. 15: Kantapan J, Dechsupa N, Tippanya D, Nobnop W, Chitapanarux I. Gallotannin from Bouea macrophylla Seed Extract Suppresses Cancer Stem-like Cells and Radiosensitizes Head and Neck Cancer. Int J Mol Sci. 2021 Aug 26;22(17):9253. doi: 10.3390/ijms22179253. PMID: 34502158; PMCID: PMC8431567. 16: Ahmed B, Syed A, Ali K, Elgorban AM, Khan A, Lee J, Al-Shwaiman HA. Synthesis of gallotannin capped iron oxide nanoparticles and their broad spectrum biological applications. RSC Adv. 2021 Mar 8;11(17):9880-9893. doi: 10.1039/d1ra00220a. PMID: 35423492; PMCID: PMC8695504. 17: Kamarudin NA, Nik Salleh NNH, Tan SC. Gallotannin-Enriched Fraction from Quercus infectoria Galls as an Antioxidant and Inhibitory Agent against Human Glioblastoma Multiforme. Plants (Basel). 2021 Nov 25;10(12):2581. doi: 10.3390/plants10122581. PMID: 34961052; PMCID: PMC8708140. 18: Savelyev N, Baykuzina P, Dokudovskaya S, Lavrik O, Rubtsova M, Dontsova O. Comprehensive analysis of telomerase inhibition by gallotannin. Oncotarget. 2018 Apr 10;9(27):18712-18719. doi: 10.18632/oncotarget.24642. PMID: 29721155; PMCID: PMC5922349. 19: Machida S, Sugaya M, Saito H, Uchiyama T. Synthesis and Evaluation of Gallotannin Derivatives as Antioxidants and α-Glucosidase Inhibitors. Chem Pharm Bull (Tokyo). 2021;69(12):1209-1212. doi: 10.1248/cpb.c21-00566. PMID: 34853289.