Ellagic Acid | CAS#476-66-4 | HDAC modulator

MedKoo Cat#: 540115 | Name: Ellagic Acid

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Description:

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

Ellagic Acid is an HDAC modulator found in fruit. It displays a variety of activities, including suppressing neovascular and angiogenesis, preventing airway hyperresponsiveness in allergy models, inhibiting cellular proliferation and inducing apoptosis in pancreatic adenocarcinoma cells, and limiting proliferation of Plasmodium and Rhinovirus.

Chemical Structure

Ellagic Acid

CAS#476-66-4

Theoretical Analysis

MedKoo Cat#: 540115

Name: Ellagic Acid

CAS#: 476-66-4

Chemical Formula: C14H6O8

Exact Mass: 302.0063

Molecular Weight: 302.19

Elemental Analysis: C, 55.64; H, 2.00; O, 42.35

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 weeks
10g	USD 450.00	2 weeks

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Related CAS #

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Synonym

Alizarine Yellow; Benzoaric acid; Lagistase; Eleagic acid; Elagostasine; Gallogen; TBBD;

IUPAC/Chemical Name

2,3,7,8-tetrahydroxychromeno[5,4,3-cde]chromene-5,10-dione

InChi Key

AFSDNFLWKVMVRB-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H

SMILES Code

O=C1C2=CC(O)=C(O)C(O3)=C2C4=C(C3=O)C=C(O)C(O)=C4O1

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ellagic acid acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM.

In vitro activity:

EA (Ellagic acid) was dissolved in dimethyl sulfoxide (DMSO) and added to the serum-free medium, ensuring that the final concentration of DMSO was below 1%. EA suppressed the secretion of VLDL (apoB) at the 50 µM concentration compared to the secretion in the untreated control using ELISA (Figure 3a). Reference: Molecules. 2021 Jul; 26(13): 3885. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8271888/

In vivo activity:

EA (Ellagic acid) (25, 50, 100 mg/kg) significantly prevented (day 21; p < 0.05, p < 0.001, p < 0.001) 3-NP induced increase of latency to traverse the narrow beam in relation to rats that received 3-NP alone (Fig. 2a). Daily treatment of rats with EA (50 and 100 mg/kg) prevented (day 21; p < 0.001) the 3-NP triggered paw slips relative to rats that received 3-NP only (Fig. 2b). EA at dose 25 mg/kg also lowered (day 7, 14, p < 0.01) the number of paw slips in 3-NP administered rats (Fig. 2b). The present results indicated that 3-NP induced characteristic features of Huntington’s disease (motor and hind-limb impairment) in rats were significantly attenuated by EA pre-treatment. Reference: Naunyn Schmiedebergs Arch Pharmacol. 2021 Jun 1. https://pubmed.ncbi.nlm.nih.gov/34061228/

	Solvent	mg/mL	mM
Solubility
	DMSO	1.4	4.50

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 302.19 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

Formulation protocol:

1. Ieda A, Wada M, Moriyasu Y, Okuno Y, Zaima N, Moriyama T. Ellagic Acid Suppresses ApoB Secretion and Enhances ApoA-1 Secretion from Human Hepatoma Cells, HepG2. Molecules. 2021 Jun 25;26(13):3885. doi: 10.3390/molecules26133885. PMID: 34202121; PMCID: PMC8271888. 2. Kumar S, Kumar R, Kumari M, Kumari R, Saha S, Bhavesh NS, Maiti TK. Ellagic Acid Inhibits α-Synuclein Aggregation at Multiple Stages and Reduces Its Cytotoxicity. ACS Chem Neurosci. 2021 Jun 2;12(11):1919-1930. doi: 10.1021/acschemneuro.1c00001. Epub 2021 May 20. PMID: 34015214. 3. Sharma P, Kumar M, Bansal N. Ellagic acid prevents 3-nitropropionic acid induced symptoms of Huntington's disease. Naunyn Schmiedebergs Arch Pharmacol. 2021 Jun 1. doi: 10.1007/s00210-021-02106-1. Epub ahead of print. PMID: 34061228. 4. Park WY, Park J, Ahn KS, Kwak HJ, Um JY. Ellagic acid induces beige remodeling of white adipose tissue by controlling mitochondrial dynamics and SIRT3. FASEB J. 2021 Jun;35(6):e21548. doi: 10.1096/fj.202002491R. PMID: 33956354.

In vitro protocol:

In vivo protocol:

1. Sharma P, Kumar M, Bansal N. Ellagic acid prevents 3-nitropropionic acid induced symptoms of Huntington's disease. Naunyn Schmiedebergs Arch Pharmacol. 2021 Jun 1. doi: 10.1007/s00210-021-02106-1. Epub ahead of print. PMID: 34061228. 2. Park WY, Park J, Ahn KS, Kwak HJ, Um JY. Ellagic acid induces beige remodeling of white adipose tissue by controlling mitochondrial dynamics and SIRT3. FASEB J. 2021 Jun;35(6):e21548. doi: 10.1096/fj.202002491R. PMID: 33956354.

1: Gopalakrishnan L, Ramana LN, Sethuraman S, Krishnan UM. Ellagic acid encapsulated chitosan nanoparticles as anti-hemorrhagic agent. Carbohydr Polym. 2014 Oct 13;111:215-21. doi: 10.1016/j.carbpol.2014.03.093. Epub 2014 Apr 6. PubMed PMID: 25037345. 2: Gu L, Deng WS, Liu Y, Jiang CH, Sun LC, Sun XF, Xu Q, Zhou H. Ellagic acid protects Lipopolysaccharide/D-galactosamine-induced acute hepatic injury in mice. Int Immunopharmacol. 2014 Oct;22(2):341-5. doi: 10.1016/j.intimp.2014.07.005. Epub 2014 Jul 16. PubMed PMID: 25038320. 3: Galano A, Francisco Marquez M, Pérez-González A. Ellagic acid: an unusually versatile protector against oxidative stress. Chem Res Toxicol. 2014 May 19;27(5):904-18. doi: 10.1021/tx500065y. Epub 2014 Apr 14. PubMed PMID: 24697747. 4: El-Shitany NA, El-Bastawissy EA, El-desoky K. Ellagic acid protects against carrageenan-induced acute inflammation through inhibition of nuclear factor kappa B, inducible cyclooxygenase and proinflammatory cytokines and enhancement of interleukin-10 via an antioxidant mechanism. Int Immunopharmacol. 2014 Apr;19(2):290-9. doi: 10.1016/j.intimp.2014.02.004. Epub 2014 Feb 15. PubMed PMID: 24534771. 5: Ahad A, Ganai AA, Mujeeb M, Siddiqui WA. Ellagic acid, an NF-κB inhibitor, ameliorates renal function in experimental diabetic nephropathy. Chem Biol Interact. 2014 Aug 5;219:64-75. doi: 10.1016/j.cbi.2014.05.011. Epub 2014 May 28. PubMed PMID: 24877639. 6: Mansouri MT, Naghizadeh B, Ghorbanzadeh B. Ellagic acid enhances morphine analgesia and attenuates the development of morphine tolerance and dependence in mice. Eur J Pharmacol. 2014 Oct 15;741:272-80. doi: 10.1016/j.ejphar.2014.08.024. Epub 2014 Aug 30. PubMed PMID: 25179576. 7: Zhang T, Chen HS, Wang LF, Bai MH, Wang YC, Jiang XF, Liu M. Ellagic acid exerts anti-proliferation effects via modulation of Tgf-β/Smad3 signaling in MCF-7 breast cancer cells. Asian Pac J Cancer Prev. 2014;15(1):273-6. PubMed PMID: 24528038. 8: Mishra S, Vinayak M. Role of ellagic acid in regulation of apoptosis by modulating novel and atypical PKC in lymphoma bearing mice. BMC Complement Altern Med. 2015 Aug 15;15:281. doi: 10.1186/s12906-015-0810-5. PubMed PMID: 26276710; PubMed Central PMCID: PMC4536603. 9: Park SW, Kwon MJ, Yoo JY, Choi HJ, Ahn YJ. Antiviral activity and possible mode of action of ellagic acid identified in Lagerstroemia speciosa leaves toward human rhinoviruses. BMC Complement Altern Med. 2014 May 26;14:171. doi: 10.1186/1472-6882-14-171. PubMed PMID: 24885569; PubMed Central PMCID: PMC4052798. 10: Ho CC, Huang AC, Yu CS, Lien JC, Wu SH, Huang YP, Huang HY, Kuo JH, Liao WY, Yang JS, Chen PY, Chung JG. Ellagic acid induces apoptosis in TSGH8301 human bladder cancer cells through the endoplasmic reticulum stress- and mitochondria-dependent signaling pathways. Environ Toxicol. 2014 Nov;29(11):1262-74. doi: 10.1002/tox.21857. Epub 2013 Mar 30. PubMed PMID: 23554011. 11: Zhou ZH, Liu MZ, Wang MH, Qu W, Sun JB, Liang JY, Wu FH. A new ellagic acid derivative from Polygonum runcinatum. Nat Prod Res. 2015;29(9):795-9. doi: 10.1080/14786419.2014.986727. Epub 2015 Jan 6. PubMed PMID: 25560313. 12: Alfredsson CF, Ding M, Liang QL, Sundström BE, Nånberg E. Ellagic acid induces a dose- and time-dependent depolarization of mitochondria and activation of caspase-9 and -3 in human neuroblastoma cells. Biomed Pharmacother. 2014 Feb;68(1):129-35. doi: 10.1016/j.biopha.2013.08.010. Epub 2013 Aug 30. PubMed PMID: 24051122. 13: García-Niño WR, Zazueta C. Ellagic acid: Pharmacological activities and molecular mechanisms involved in liver protection. Pharmacol Res. 2015 Jul;97:84-103. doi: 10.1016/j.phrs.2015.04.008. Epub 2015 May 2. Review. PubMed PMID: 25941011. 14: Allahverdi TD, Allahverdi E, Yayla S, Deprem T, Merhan O, Vural S. The comparison of the effects of ellagic acid and diclofenac sodium on intra-abdominal adhesion: an in vivo study in the rat model. Int Surg. 2014 Sep-Oct;99(5):543-50. doi: 10.9738/INTSURG-D-14-00065.1. PubMed PMID: 25216418; PubMed Central PMCID: PMC4253921. 15: Yan L, Yin P, Ma C, Liu Y. Method development and validation for pharmacokinetic and tissue distributions of ellagic acid using ultrahigh performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Molecules. 2014 Nov 18;19(11):18923-35. doi: 10.3390/molecules191118923. PubMed PMID: 25412040. 16: Mişe Yonar S, Yonar ME, Yöntürk Y, Pala A. Effect of ellagic acid on some haematological, immunological and antioxidant parameters of rainbow trout (Oncorhynchus mykiss). J Anim Physiol Anim Nutr (Berl). 2014 Oct;98(5):936-41. doi: 10.1111/jpn.12162. Epub 2014 Jan 9. PubMed PMID: 24401136. 17: Dubey A, Park DW, Kwon JE, Jeong YJ, Kim T, Kim I, Kang SC, Chi KW. Investigation of the biological and anti-cancer properties of ellagic acid-encapsulated nano-sized metalla-cages. Int J Nanomedicine. 2015 Sep 2;10 Spec Iss:227-40. doi: 10.2147/IJN.S88289. eCollection 2015. PubMed PMID: 26366074; PubMed Central PMCID: PMC4562765. 18: Wubshet SG, Moresco HH, Tahtah Y, Brighente IM, Staerk D. High-resolution bioactivity profiling combined with HPLC-HRMS-SPE-NMR: α-Glucosidase inhibitors and acetylated ellagic acid rhamnosides from Myrcia palustris DC. (Myrtaceae). Phytochemistry. 2015 Aug;116:246-52. doi: 10.1016/j.phytochem.2015.04.004. Epub 2015 Apr 30. PubMed PMID: 25935545. 19: Ortiz-Ruiz CV, Berna J, Tudela J, Varon R, Garcia-Canovas F. Action of ellagic acid on the melanin biosynthesis pathway. J Dermatol Sci. 2016 May;82(2):115-22. doi: 10.1016/j.jdermsci.2016.02.004. Epub 2016 Feb 12. PubMed PMID: 26899308. 20: Girish C, Shweta O, Raj V, Balakrishnan S, Varghese RG. Ellagic acid modulates sodium valproate induced reproductive toxicity in male Wistar rats. Indian J Physiol Pharmacol. 2014 Oct-Dec;58(4):416-22. PubMed PMID: 26215011.