Dioxinodehydroeckol | CAS#639514-05-9 | Phlorotannin

MedKoo Cat#: 463407 | Name: Dioxinodehydroeckol

Description:

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

Eckstolonol (Dioxinodehydroeckol) is a phlorotannin found in the edible brown algae arame (Eisenia bicyclis) and turuarame (Ecklonia stolonifera).

Chemical Structure

Dioxinodehydroeckol

CAS#639514-05-9

Theoretical Analysis

MedKoo Cat#: 463407

Name: Dioxinodehydroeckol

CAS#: 639514-05-9

Chemical Formula: C18H10O9

Exact Mass: 370.0325

Molecular Weight: 370.27

Elemental Analysis: C, 58.39; H, 2.72; O, 38.89

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Dioxinodehydroeckol; Eckstolonol;

IUPAC/Chemical Name

Benzo(1,2-b:3,4-b')bis(1,4)benzodioxin-1,3,6,9,11-pentol

InChi Key

LBHQACSAGWCMAB-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H10O9/c19-6-1-8(21)14-11(3-6)26-17-13(24-14)5-10(23)16-18(17)27-15-9(22)2-7(20)4-12(15)25-16/h1-5,19-23H

SMILES Code

Oc1cc2c(Oc3c4c(Oc5c(O4)cc(O)cc5O)cc(O)c3O2)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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 370.27 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: Seong SH, Paudel P, Jung HA, Choi JS. Identifying Phlorofucofuroeckol-A as a Dual Inhibitor of Amyloid-β25-35 Self-Aggregation and Insulin Glycation: Elucidation of the Molecular Mechanism of Action. Mar Drugs. 2019 Oct 23;17(11):600. doi: 10.3390/md17110600. PMID: 31652867; PMCID: PMC6891666. 2: Xi M, Dragsted LO. Biomarkers of seaweed intake. Genes Nutr. 2019 Aug 14;14:24. doi: 10.1186/s12263-019-0648-4. PMID: 31428206; PMCID: PMC6694598. 3: Baldrick FR, McFadden K, Ibars M, Sung C, Moffatt T, Megarry K, Thomas K, Mitchell P, Wallace JMW, Pourshahidi LK, Ternan NG, Corona G, Spencer J, Yaqoob P, Hotchkiss S, Campbell R, Moreno-Rojas JM, Cuevas FJ, Pereira-Caro G, Rowland I, Gill CIR. Impact of a (poly)phenol-rich extract from the brown algae Ascophyllum nodosum on DNA damage and antioxidant activity in an overweight or obese population: a randomized controlled trial. Am J Clin Nutr. 2018 Oct 1;108(4):688-700. doi: 10.1093/ajcn/nqy147. PMID: 30321272. 4: Ahn BN, Karadeniz F, Kong CS, Nam KH, Jang MS, Seo Y, Kim HS. Dioxinodehydroeckol Enhances the Differentiation of Osteoblasts by Regulating the Expression of Phospho-Smad1/5/8. Mar Drugs. 2016 Sep 14;14(9):168. doi: 10.3390/md14090168. PMID: 27649211; PMCID: PMC5039539. 5: Ryu B, Ahn BN, Kang KH, Kim YS, Li YX, Kong CS, Kim SK, Kim DG. Dioxinodehydroeckol protects human keratinocyte cells from UVB-induced apoptosis modulated by related genes Bax/Bcl-2 and caspase pathway. J Photochem Photobiol B. 2015 Dec;153:352-7. doi: 10.1016/j.jphotobiol.2015.10.018. Epub 2015 Oct 25. PMID: 26529485. 6: 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. PMID: 24628384. 7: 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. PMID: 24334103. 8: Bak SS, Ahn BN, Kim JA, Shin SH, Kim JC, Kim MK, Sung YK, Kim SK. Ecklonia cava promotes hair growth. Clin Exp Dermatol. 2013 Dec;38(8):904-10. doi: 10.1111/ced.12120. PMID: 24252083. 9: Jung HA, Jin SE, Ahn BR, Lee CM, Choi JS. Anti-inflammatory activity of edible brown alga Eisenia bicyclis and its constituents fucosterol and phlorotannins in LPS-stimulated RAW264.7 macrophages. Food Chem Toxicol. 2013 Sep;59:199-206. doi: 10.1016/j.fct.2013.05.061. Epub 2013 Jun 14. PMID: 23774261. 10: Eom SH, Lee DS, Kang YM, Son KT, Jeon YJ, Kim YM. Application of yeast Candida utilis to ferment Eisenia bicyclis for enhanced antibacterial effect. Appl Biochem Biotechnol. 2013 Oct;171(3):569-82. doi: 10.1007/s12010-013-0288-x. Epub 2013 May 23. PMID: 23700145. 11: Kang YM, Eom SH, Kim YM. Protective effect of phlorotannins from Eisenia bicyclis against lipopolysaccharide-stimulated inflammation in HepG2 cells. Environ Toxicol Pharmacol. 2013 May;35(3):395-401. doi: 10.1016/j.etap.2013.01.009. Epub 2013 Jan 30. PMID: 23454824. 12: Ahn BR, Moon HE, Kim HR, Jung HA, Choi JS. Neuroprotective effect of edible brown alga Eisenia bicyclis on amyloid beta peptide-induced toxicity in PC12 cells. Arch Pharm Res. 2012 Nov;35(11):1989-98. doi: 10.1007/s12272-012-1116-5. Epub 2012 Dec 4. PMID: 23212641. 13: Lee MS, Yoon HD, Kim JI, Choi JS, Byun DS, Kim HR. Dioxinodehydroeckol inhibits melanin synthesis through PI3K/Akt signalling pathway in α-melanocyte- stimulating hormone-treated B16F10 cells. Exp Dermatol. 2012 Jun;21(6):471-3. doi: 10.1111/j.1600-0625.2012.01508.x. PMID: 22621193. 14: Eom SH, Lee SH, Yoon NY, Jung WK, Jeon YJ, Kim SK, Lee MS, Kim YM. α-Glucosidase- and α-amylase-inhibitory activities of phlorotannins from Eisenia bicyclis. J Sci Food Agric. 2012 Aug 15;92(10):2084-90. doi: 10.1002/jsfa.5585. Epub 2012 Jan 23. PMID: 22271637. 15: 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. doi: 10.1271/bbb.110137. Epub 2011 Aug 7. PMID: 21821954. 16: Jung HA, Oh SH, Choi JS. Molecular docking studies of phlorotannins from Eisenia bicyclis with BACE1 inhibitory activity. Bioorg Med Chem Lett. 2010 Jun 1;20(11):3211-5. doi: 10.1016/j.bmcl.2010.04.093. Epub 2010 Apr 24. PMID: 20462757. 17: Kim SK, Kong CS. Anti-adipogenic effect of dioxinodehydroeckol via AMPK activation in 3T3-L1 adipocytes. Chem Biol Interact. 2010 Jun 7;186(1):24-9. doi: 10.1016/j.cbi.2010.04.003. Epub 2010 Apr 10. PMID: 20385110. 18: Shim SY, Choi JS, Byun DS. Inhibitory effects of phloroglucinol derivatives isolated from Ecklonia stolonifera on Fc(epsilon)RI expression. Bioorg Med Chem. 2009 Jul 1;17(13):4734-9. doi: 10.1016/j.bmc.2009.04.050. Epub 2009 May 3. PMID: 19443227. 19: Kong CS, Kim JA, Yoon NY, Kim SK. Induction of apoptosis by phloroglucinol derivative from Ecklonia Cava in MCF-7 human breast cancer cells. Food Chem Toxicol. 2009 Jul;47(7):1653-8. doi: 10.1016/j.fct.2009.04.013. Epub 2009 Apr 22. PMID: 19393283. 20: Yoon NY, Eom TK, Kim MM, Kim SK. Inhibitory effect of phlorotannins isolated from Ecklonia cava on mushroom tyrosinase activity and melanin formation in mouse B16F10 melanoma cells. J Agric Food Chem. 2009 May 27;57(10):4124-9. doi: 10.1021/jf900006f. Epub 2009 Apr 10. PMID: 19361156.