Ellagic acid

Modify Date: 2024-01-02 17:17:49

Ellagic acid Structure
Ellagic acid structure
 Common Name Ellagic acid
CAS Number 476-66-4 Molecular Weight 302.193
Density 2.1±0.1 g/cm3 Boiling Point 796.5±60.0 °C at 760 mmHg
Molecular Formula C14H6O8 Melting Point ≥350 °C
MSDS Chinese USA Flash Point 310.1±26.4 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Ellagic acid


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

 Names

Name ellagic acid
Synonym More Synonyms

 Ellagic acid Biological Activity

Description Ellagic acid is a natural antioxidant, and acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM.
Related Catalog
Target

CK2:40 nM (IC50)

In Vitro Ellagic acid is a potent CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM. Ellagic acid also blocks other kinases such as LYN, PKA, SYK, GSK3, FGR and CK1, with IC50s of 2.9, 3.5, 4.3, 7.5, 9.4 and 13.0 μM, respectively, and shows no obvious effects on DYRK1a, CSK, NPM-ALK, RET and FLT3 (IC50s > 40 μM). Ellagic acid (5-100 μM) shows inhibitory activities against Karpas299, SUDHL1, SR786, and FE-PD cell lines[1]. Ellagic acid (10 μM) exhibits cytotoxic effects on MCF-7 cells after treatment of radiation. Ellagic acid (10 μM) in combination with Irradiation (IR) significantly abridges the capacity of MCF-7 cells to form colonies equated with individual treatments. Ellagic acid with IR also induces cell apoptosis, and facilitates the upregulation of pro-apopttotic Bax and downregulation of Bcl-2 in MCF-7 cells[3].
In Vivo Ellagic acid (EA; 10 mg/kg/day; p.o., 14 days) strongly decreases MDA brain content by 17%, and reduces the levels of brain TNF-α by 42% in rats. Ellagic acid markedly increases the reduced brain contents of 5-HT (39%), dopamine (DA, 71%), and norepinephrine (NE, 77%). Ellagic acid (10 mg/kg, p.o., 14 days) causes decreased histopathological changes induced by Doxorubicin in rats[2].
Kinase Assay CK2 and CK1 phosphorylation assays are carried out at 37°C in the presence of increasing amounts of each inhibitor (Ellagic acid) in a final volume of 25 µL containing 50 mM, Tris-HCl pH 7.5, 100 mM NaCl, 12 mM MgCl2, 0.02 mM [33P-ATP] (500-1000 cpm/pmol), unless otherwise indicated. The phosphorylatable substrates are the synthetic peptide substrate RRRADDSDDDDD (100 µM) and RRKHAAIGDDDDAYSITA (200 µM) for CK2 and CK1, respectively. Reaction started with the addition of the kinase and is stopped after 10 min. by addition of 5 µL of 0.5 M orthophosphoric acid before spotting aliquots onto phosphocellulose filters. Filters are washed in 75 mM phosphoric acid substrate following SDS-PAGE of the radiolabeled samples. DYRK1A, assayed on the peptide RRRFRPASPLRGPPK, and tyrosine kinase activities are determined[1].
Cell Assay ALCL cell viability is measured by MTT assay. Briefly, 0.1 × 105 cells are seeded onto 96-well microculture plates 12 hrs before adding ellagic acid. The cells are grown in 200 µL of complete RPMI-1640 medium, under standard tissue-culture conditions, in the presence or absence of the drug (Ellagic acid) for 48 hours. Twenty µL of MTT solution (5 mg/mL) are then added to the cell suspension for 4h. The intracellular formazan crystals are dissolved with 150 µL of DMSO and optical density, measured on a spectrophotometer at 540 nm, represents the mean (± SD) of triplicate cultures[1].
Animal Admin Fifty male adult Sprague-Dawley rats are divided randomly into five groups as follow: Group (1) receives corn oil orally as a vehicle and served as normal control. Group (2) receives doxorubicin (DOX) injection (5 mg/kg, i.p.) twice a week for 14 days. Group (3) receives Ellagic acid (10 mg/kg, p.o.; daily) for 14 days and DOX (5 mg/kg, i.p.) twice a week for 14 days. Group (4) receives rosmarinic acid (RA; 75 mg/kg, p.o.; daily) for 14 days and DOX (5 mg/kg, i.p.) twice a week for 14 days. Group (5) receives Ellagic acid (10 mg/kg, p.o.; daily) with RA (75 mg/kg, p.o.; daily) for 14 days and DOX injection (5 mg/kg, i.p.) twice a week for 14 days[2].
References

[1]. Cozza G, et al. Identification of ellagic acid as potent inhibitor of protein kinase CK2: a successful example of a virtual screening application. J Med Chem. 2006 Apr 20;49(8):2363-6.

[2]. Rizk HA, et al. Prophylactic effects of ellagic acid and rosmarinic acid on doxorubicin-induced neurotoxicity in rats. J Biochem Mol Toxicol. 2017 Dec;31(12).

[3]. Ahire V, et al. Ellagic Acid Enhances Apoptotic Sensitivity of Breast Cancer Cells to γ-Radiation. Nutr Cancer. 2017 Aug-Sep;69(6):904-910.

 Chemical & Physical Properties

Density 2.1±0.1 g/cm3
Boiling Point 796.5±60.0 °C at 760 mmHg
Melting Point ≥350 °C
Molecular Formula C14H6O8
Molecular Weight 302.193
Flash Point 310.1±26.4 °C
Exact Mass 302.006256
PSA 141.34000
LogP 0.52
Vapour Pressure 0.0±2.9 mmHg at 25°C
Index of Refraction 1.895
Storage condition Store at RT
Stability Stable. Combustible. Incompatible with strong oxidizing agents.
Water Solubility 1 M NaOH: 10 mg/mL, dark green | <0.1 g/100 mL at 21 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DJ2620000
CHEMICAL NAME :
(1)Benzopyrano(5,4,3-cde)(1)benzopyran-5,10-dione, 2,3,7,8-tetrahydroxy-
CAS REGISTRY NUMBER :
476-66-4
BEILSTEIN REFERENCE NO. :
0047549
LAST UPDATED :
199706
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C14-H6-O8
MOLECULAR WEIGHT :
302.20

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
1208 mg/kg
SEX/DURATION :
female 16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow)
REFERENCE :
AMBPBZ Acta Pathologica et Microbiologica Scandinavica, Section A: Pathology. (Copenhagen, Denmark) V.78-89, 1970-81. For publisher information, see ACPADQ. Volume(issue)/page/year: 79,487,1971 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - E0173 No. of Facilities: 42 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 350 (estimated) No. of Female Employees: 285 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi:Irritant
Risk Phrases R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS DJ2620000

 Synthetic Route

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 Synonyms

lagistase
2,3,7,8-Tetrahydroxychromeno[5,4,3-cde]chromene-5,10-dione
Ellagic acid
Elllagic Acid
elagostasine
MFCD00006914
EINECS 207-508-3
eleagicacid
Ellagic
BENZOARIC ACID
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