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MedKoo Cat#: 584381 | Name: Eckol

Description:

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

Eckol inhibits ultraviolet B-induced cell damage in human keratinocytes via a decrease in oxidative stress.

Chemical Structure

Eckol
Eckol
CAS#88798-74-7

Theoretical Analysis

MedKoo Cat#: 584381

Name: Eckol

CAS#: 88798-74-7

Chemical Formula: C18H12O9

Exact Mass: 372.0481

Molecular Weight: 372.29

Elemental Analysis: C, 58.07; H, 3.25; O, 38.68

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Eckol
IUPAC/Chemical Name
1-(3,5-Dihydroxyphenoxy)-2,4,7,9-tetrahydroxydibenzo-1,4-dioxin
InChi Key
PCZZRBGISTUIOA-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H12O9/c19-7-1-8(20)3-10(2-7)25-16-12(23)6-13(24)17-18(16)27-15-11(22)4-9(21)5-14(15)26-17/h1-6,19-24H
SMILES Code
OC1=C2OC3=C(OC4=CC(O)=CC(O)=C4)C(O)=CC(O)=C3OC2=CC(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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 372.29 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
1: Aremu AO, Masondo NA, Rengasamy KR, Amoo SO, Gruz J, Bíba O, Šubrtová M, Pěnčík A, Novák O, Doležal K, Van Staden J. Physiological role of phenolic biostimulants isolated from brown seaweed Ecklonia maxima on plant growth and development. Planta. 2015 Jun;241(6):1313-24. doi: 10.1007/s00425-015-2256-x. Epub 2015 Feb 12. PubMed PMID: 25672504. 2: Piao MJ, Lee NH, Chae S, Hyun JW. Eckol inhibits ultraviolet B-induced cell damage in human keratinocytes via a decrease in oxidative stress. Biol Pharm Bull. 2012;35(6):873-80. PubMed PMID: 22687478. 3: Moon C, Kim SH, Kim JC, Hyun JW, Lee NH, Park JW, Shin T. Protective effect of phlorotannin components phloroglucinol and eckol on radiation-induced intestinal injury in mice. Phytother Res. 2008 Feb;22(2):238-42. PubMed PMID: 17886227. 4: Kim TH, Lee T, Ku SK, Bae JS. Vascular barrier protective effects of eckol and its derivatives. Bioorg Med Chem Lett. 2012 Jun 1;22(11):3710-2. doi: 10.1016/j.bmcl.2012.04.026. Epub 2012 Apr 12. PubMed PMID: 22543027. 5: Lee MS, Shin T, Utsuki T, Choi JS, Byun DS, Kim HR. Isolation and identification of phlorotannins from Ecklonia stolonifera with antioxidant and hepatoprotective properties in tacrine-treated HepG2 cells. J Agric Food Chem. 2012 May 30;60(21):5340-9. doi: 10.1021/jf300157w. Epub 2012 May 21. PubMed PMID: 22587607. 6: Kim TH, Ku SK, Bae JS. Antithrombotic and profibrinolytic activities of eckol and dieckol. J Cell Biochem. 2012 Sep;113(9):2877-83. doi: 10.1002/jcb.24163. PubMed PMID: 22511271. 7: Choi JG, Kang OH, Brice OO, Lee YS, Chae HS, Oh YC, Sohn DH, Park H, Choi HG, Kim SG, Shin DW, Kwon DY. Antibacterial activity of Ecklonia cava against methicillin-resistant Staphylococcus aureus and Salmonella spp. Foodborne Pathog Dis. 2010 Apr;7(4):435-41. doi: 10.1089/fpd.2009.0434. PubMed PMID: 20001325. 8: Kim TH, Ku SK, Lee T, Bae JS. Vascular barrier protective effects of phlorotannins on HMGB1-mediated proinflammatory responses in vitro and in vivo. Food Chem Toxicol. 2012 Jun;50(6):2188-95. doi: 10.1016/j.fct.2012.03.082. Epub 2012 Apr 13. PubMed PMID: 22504532. 9: Joe MJ, Kim SN, Choi HY, Shin WS, Park GM, Kang DW, Kim YK. The inhibitory effects of eckol and dieckol from Ecklonia stolonifera on the expression of matrix metalloproteinase-1 in human dermal fibroblasts. Biol Pharm Bull. 2006 Aug;29(8):1735-9. PubMed PMID: 16880634. 10: Jun YJ, Lee M, Shin T, Yoon N, Kim JH, Kim HR. eckol enhances heme oxygenase-1 expression through activation of Nrf2/JNK pathway in HepG2 cells. Molecules. 2014 Sep 29;19(10):15638-52. doi: 10.3390/molecules191015638. PubMed PMID: 25268719. 11: Yoon NY, Kim HR, Chung HY, Choi JS. Anti-hyperlipidemic effect of an edible brown algae, Ecklonia stolonifera, and its constituents on poloxamer 407-induced hyperlipidemic and cholesterol-fed rats. Arch Pharm Res. 2008 Dec;31(12):1564-71. doi: 10.1007/s12272-001-2152-8. Epub 2008 Dec 20. PubMed PMID: 19099225. 12: Fukuyama Y, Kodama M, Miura I, Kinzyo Z, Kido M, Mori H, Nakayama Y, Takahashi M. Structure of an anti-plasmin inhibitor, eckol, isolated from the brown alga Ecklonia kurome Okamura and inhibitory activities of its derivatives on plasma plasmin inhibitors. Chem Pharm Bull (Tokyo). 1989 Feb;37(2):349-53. PubMed PMID: 2525966. 13: Jung HA, Jung HJ, Jeong HY, Kwon HJ, Ali MY, Choi JS. Phlorotannins isolated from the edible brown alga Ecklonia stolonifera exert anti-adipogenic activity on 3T3-L1 adipocytes by downregulating C/EBPα and PPARγ. Fitoterapia. 2014 Jan;92:260-9. doi: 10.1016/j.fitote.2013.12.003. Epub 2013 Dec 12. PubMed PMID: 24334103. 14: Park E, Lee NH, Joo HG, Jee Y. Modulation of apoptosis of eckol against ionizing radiation in mice. Biochem Biophys Res Commun. 2008 Aug 8;372(4):792-7. doi: 10.1016/j.bbrc.2008.05.140. Epub 2008 Jun 2. PubMed PMID: 18522802. 15: Eom SH, Lee MS, Lee EW, Kim YM, Kim TH. Pancreatic lipase inhibitory activity of phlorotannins isolated from Eisenia bicyclis. Phytother Res. 2013 Jan;27(1):148-51. doi: 10.1002/ptr.4694. Epub 2012 Apr 4. PubMed PMID: 22473750. 16: Kang KA, Lee KH, Chae S, Zhang R, Jung MS, Lee Y, Kim SY, Kim HS, Joo HG, Park JW, Ham YM, Lee NH, Hyun JW. Eckol isolated from Ecklonia cava attenuates oxidative stress induced cell damage in lung fibroblast cells. FEBS Lett. 2005 Nov 21;579(28):6295-304. Epub 2005 Oct 19. PubMed PMID: 16253238. 17: Moon HE, Islam N, Ahn BR, Chowdhury SS, Sohn HS, Jung HA, Choi JS. Protein tyrosine phosphatase 1B and α-glucosidase inhibitory Phlorotannins from edible brown algae, Ecklonia stolonifera and Eisenia bicyclis. Biosci Biotechnol Biochem. 2011;75(8):1472-80. Epub 2011 Aug 7. PubMed PMID: 21821954. 18: Kang MC, Cha SH, Wijesinghe WA, Kang SM, Lee SH, Kim EA, Song CB, Jeon YJ. Protective effect of marine algae phlorotannins against AAPH-induced oxidative stress in zebrafish embryo. Food Chem. 2013 Jun 1;138(2-3):950-5. doi: 10.1016/j.foodchem.2012.11.005. Epub 2012 Nov 12. PubMed PMID: 23411200. 19: Jung HA, Kim JI, Choung SY, Choi JS. Protective effect of the edible brown alga Ecklonia stolonifera on doxorubicin-induced hepatotoxicity in primary rat hepatocytes. J Pharm Pharmacol. 2014 Aug;66(8):1180-8. doi: 10.1111/jphp.12241. Epub 2014 Mar 13. PubMed PMID: 24628384. 20: Glombitza KW, Vogels HP. Antibiotics from Algae. XXXV. Phlorotannins from Ecklonia maxima1. Planta Med. 1985 Aug;51(4):308-12. PubMed PMID: 17340520.