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MedKoo Cat#: 145702 | Name: Dieckol

Description:

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

Dieckol is a bioactive compound found in Ecklonia cava, a type of brown seaweed commonly found in coastal areas of Korea and Japan. It is known for its potent antioxidant, anti-inflammatory, and anti-cancer properties. Dieckol has been studied for its potential health benefits, including protecting cells from oxidative stress, reducing inflammation, and possibly supporting cardiovascular health.

Chemical Structure

Dieckol
CAS#88095-77-6

Theoretical Analysis

MedKoo Cat#: 145702

Name: Dieckol

CAS#: 88095-77-6

Chemical Formula: C36H22O18

Exact Mass: 742.0800

Molecular Weight: 742.55

Elemental Analysis: C, 58.23; H, 2.99; O, 38.78

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
Dieckol;
IUPAC/Chemical Name
4-(4-((6-(3,5-dihydroxyphenoxy)-4,7,9-trihydroxydibenzo[b,e][1,4]dioxin-2-yl)oxy)-3,5-dihydroxyphenoxy)dibenzo[b,e][1,4]dioxine-1,3,6,8-tetraol
InChi Key
DRZQFGYIIYNNEC-UHFFFAOYSA-N
InChi Code
1S/C36H22O18/c37-12-1-13(38)3-15(2-12)49-31-22(44)10-25(47)34-35(31)54-30-21(43)8-17(9-27(30)52-34)48-28-19(41)6-16(7-20(28)42)50-32-23(45)11-24(46)33-36(32)53-29-18(40)4-14(39)5-26(29)51-33/h1-11,37-47H
SMILES Code
OC1=CC(OC2=C(O)C=C(O)C3=C2OC4=C(O3)C=C(OC5=C(O)C=C(OC6=C(O)C=C(O)C7=C6OC8=C(O7)C=C(O)C=C8O)C=C5O)C=C4O)=CC(O)=C1
Appearance
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 742.55 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: Rajan DK, Mohan K, Zhang S, Ganesan AR. Dieckol: a brown algal phlorotannin with biological potential. Biomed Pharmacother. 2021 Oct;142:111988. doi: 10.1016/j.biopha.2021.111988. Epub 2021 Aug 7. PMID: 34371307. 2: Li H, Oh SH, Shin HC, Suh MW. Intratympanic Administration of Dieckol Prevents Ototoxic Hearing Loss. Mar Drugs. 2022 Sep 30;20(10):622. doi: 10.3390/md20100622. PMID: 36286446; PMCID: PMC9604621. 3: Jo MH, Kim YT, Park SJ. Dieckol Inhibits Autophagic Flux and Induces Apoptotic Cell Death in A375 Human Melanoma Cells via Lysosomal Dysfunction and Mitochondrial Membrane Impairment. Int J Mol Sci. 2022 Nov 16;23(22):14149. doi: 10.3390/ijms232214149. PMID: 36430634; PMCID: PMC9696613. 4: Heo SY, Jeong MS, Lee HS, Park WS, Choi IW, Yi M, Jung WK. Dieckol induces cell cycle arrest by down-regulating CDK2/cyclin E in response to p21/p53 activation in human tracheal fibroblasts. Cell Biochem Funct. 2022 Jan;40(1):71-78. doi: 10.1002/cbf.3675. Epub 2021 Oct 27. PMID: 34708431. 5: Li Z, Wang Y, Zhao J, Zhang H. Dieckol attenuates the nociception and inflammatory responses in different nociceptive and inflammatory induced mice model. Saudi J Biol Sci. 2021 Sep;28(9):4891-4899. doi: 10.1016/j.sjbs.2021.06.021. Epub 2021 Jun 13. PMID: 34466063; PMCID: PMC8381058. 6: Kwack MH, Ha NG, Lee WJ. Dieckol Inhibits the Effects of Particulate Matter 10 on Sebocytes, Outer Root Sheath Cells, and Cutibacterium Acnes-Pretreated Mice. Ann Dermatol. 2022 Jun;34(3):182-190. doi: 10.5021/ad.2022.34.3.182. Epub 2022 May 20. PMID: 35721332; PMCID: PMC9171178. 7: Kim JM, Chung KS, Yoon YS, Jang SY, Heo SW, Park G, Jang YP, Ahn HS, Shin YK, Lee SH, Lee KT. Dieckol Isolated from Eisenia bicyclis Ameliorates Wrinkling and Improves Skin Hydration via MAPK/AP-1 and TGF-β/Smad Signaling Pathways in UVB-Irradiated Hairless Mice. Mar Drugs. 2022 Dec 14;20(12):779. doi: 10.3390/md20120779. PMID: 36547926; PMCID: PMC9785544. 8: Yoon JH, Lee N, Youn K, Jo MR, Kim HR, Lee DS, Ho CT, Jun M. Dieckol Ameliorates Aβ Production via PI3K/Akt/GSK-3β Regulated APP Processing in SweAPP N2a Cell. Mar Drugs. 2021 Mar 15;19(3):152. doi: 10.3390/md19030152. PMID: 33804171; PMCID: PMC8001366. 9: Wang CH, Li XF, Jin LF, Zhao Y, Zhu GJ, Shen WZ. Dieckol inhibits non-small- cell lung cancer cell proliferation and migration by regulating the PI3K/AKT signaling pathway. J Biochem Mol Toxicol. 2019 Aug;33(8):e22346. doi: 10.1002/jbt.22346. Epub 2019 Jul 10. PMID: 31291034; PMCID: PMC6771741. 10: Byun KA, Oh S, Son M, Oh SE, Park CH, Son KH, Byun K. Dieckol-Attenuated High-Fat Diet Induced Muscle Atrophy by Modulating Muscular Deposition of Lipid Droplets. Nutrients. 2021 Sep 10;13(9):3160. doi: 10.3390/nu13093160. PMID: 34579038; PMCID: PMC8467349. 11: Zhang S, Ren H, Sun H, Cao S. Dieckol exerts anticancer activity in human osteosarcoma (MG-63) cells through the inhibition of PI3K/AKT/mTOR signaling pathway. Saudi J Biol Sci. 2021 Sep;28(9):4908-4915. doi: 10.1016/j.sjbs.2021.07.019. Epub 2021 Jul 12. PMID: 34466065; PMCID: PMC8381078. 12: Wang H, Yang L, Chao J. Antiosteoporosis and bone protective effect of dieckol against glucocorticoid-induced osteoporosis in rats. Front Endocrinol (Lausanne). 2022 Aug 19;13:932488. doi: 10.3389/fendo.2022.932488. PMID: 36060953; PMCID: PMC9437630. 13: Yoon M, Kim JS, Seo S, Lee K, Um MY, Lee J, Jung J, Cho S. Dieckol, a Major Marine Polyphenol, Enhances Non-Rapid Eye Movement Sleep in Mice via the GABAA-Benzodiazepine Receptor. Front Pharmacol. 2020 Apr 17;11:494. doi: 10.3389/fphar.2020.00494. PMID: 32362829; PMCID: PMC7181965. 14: Sugiura Y, Usui M, Katsuzaki H, Imai K, Tanaka R, Matsushita T, Miyata M. Dieckol isolated from a brown alga, Eisenia nipponica, suppresses ear swelling from allergic inflammation in mouse. J Food Biochem. 2021 Apr;45(4):e13659. doi: 10.1111/jfbc.13659. Epub 2021 Feb 17. PMID: 33595108. 15: Kwon S, Jung JH, Cho S, Moon KD, Lee J. Dieckol is a natural positive allosteric modulator of GABAA-benzodiazepine receptors and enhances inhibitory synaptic activity in cultured neurons. Nutr Neurosci. 2021 Nov;24(11):835-842. doi: 10.1080/1028415X.2019.1681089. Epub 2019 Oct 25. PMID: 31650903. 16: Irfan M, Kwon TH, Kwon HW, Rhee MH. Pharmacological actions of dieckol on modulation of platelet functions and thrombus formation via integrin αIIbβ3 and cAMP signaling. Pharmacol Res. 2022 Mar;177:106088. doi: 10.1016/j.phrs.2022.106088. Epub 2022 Jan 14. PMID: 35038555. 17: Xiao W, Liu H, Lei Y, Gao H, Alahmadi TA, Peng H, Chen W. Chemopreventive effect of dieckol against 7,12-dimethylbenz(a)anthracene induced skin carcinogenesis model by modulatory influence on biochemical and antioxidant biomarkers. Environ Toxicol. 2021 May;36(5):800-810. doi: 10.1002/tox.23082. Epub 2020 Dec 21. PMID: 33347706. 18: Shin HC, Kim Y, Choi J, Kang HB, Han SY, Park K, Hwang HJ. Regioselective Synthesis of 6-O-Acetyl Dieckol and Its Selective Cytotoxicity against Non-Small-Cell Lung Cancer Cells. Mar Drugs. 2022 Oct 29;20(11):683. doi: 10.3390/md20110683. PMID: 36355006; PMCID: PMC9695823. 19: Ahn JH, Yang YI, Lee KT, Choi JH. Dieckol, isolated from the edible brown algae Ecklonia cava, induces apoptosis of ovarian cancer cells and inhibits tumor xenograft growth. J Cancer Res Clin Oncol. 2015 Feb;141(2):255-68. doi: 10.1007/s00432-014-1819-8. Epub 2014 Sep 13. PMID: 25216701. 20: Lee MS, Lee B, Park KE, Utsuki T, Shin T, Oh CW, Kim HR. Dieckol enhances the expression of antioxidant and detoxifying enzymes by the activation of Nrf2-MAPK signalling pathway in HepG2 cells. Food Chem. 2015 May 1;174:538-46. doi: 10.1016/j.foodchem.2014.11.090. Epub 2014 Nov 22. Erratum in: Food Chem. 2016 Jul 1;202:521. PMID: 25529716.