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Ellagic acid(CAS No. 476-66-4)

Ellagic acid C14H6O8 (cas 476-66-4) Molecular Structure

476-66-4 Structure

Identification and Related Records

【Name】
Ellagic acid
【CAS Registry number】
476-66-4
【Synonyms】
Alizarinyellow
Alizarine Yellow
Benzoaric acid
C.I. 55005
C.I. 75270
Elagostasine
【EINECS(EC#)】
207-508-3
【Molecular Formula】
C14H6O8 (Products with the same molecular formula)
【Molecular Weight】
302.19264
【Inchi】
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
【InChIKey】
AFSDNFLWKVMVRB-UHFFFAOYSA-N
【Canonical SMILES】
C1=C2C3=C(C(=C1O)O)OC(=O)C4=CC(=C(C(=C43)OC2=O)O)O
【MOL File】
476-66-4.mol

Chemical and Physical Properties

【Appearance】
gray to slightly beige crystalline powder
【Density】
1.667
【Melting Point】
>360℃
【Boiling Point】
796.5°Cat760mmHg
【Vapour】
2.32E-26mmHg at 25°C
【Refractive Index】
1.894
【Flash Point】
310.1°C
【Water】
slightly soluble
【Solubilities】
slightly soluble
【Color/Form】
tan to gray
【Stability】
Stable. Combustible. Incompatible with strong oxidizing agents.
【Storage temp】
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.
【Spectral properties】
UV max (ethanol): 366, 255 nm (log epsilon 3.93, 4.60)
【Computed Properties】
Molecular Weight:302.19264 [g/mol]
Molecular Formula:C14H6O8
XLogP3-AA:1.1
H-Bond Donor:4
H-Bond Acceptor:8
Rotatable Bond Count:0
Tautomer Count:127
Exact Mass:302.006267
MonoIsotopic Mass:302.006267
Topological Polar Surface Area:134
Heavy Atom Count:22
Formal Charge:0
Complexity:475
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:4
Feature 3D Ring Count:4
Effective Rotor Count:0
Conformer Sampling RMSD:0.6
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S36
【Safety】

Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating vapors.
Safety Information for Ellagic acid (CAS NO.476-66-4)
Hazard Codes:?IrritantXi
Risk Statements:?36/37/38?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements:?26-36/37?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37: Wear suitable protective clothing and gloves.
WGK Germany:?3
RTECS:?DJ2620000
F: 8-10-23

【Sensitive】
Air & Light Sensitive
【Specification】

cream to light yellow crystalline solid
Safety Statements:26-36-36/37
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
36/37:Wear suitable protective clothing and gloves
【Octanol/Water Partition Coefficient】
log Kow = -2.05 (est)
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Prepd by sodium persulfate oxidation of gallic acid or by acid hydrolysis of crude tannin from walnuts.
Isolation from the kino of Eucalyptus maculata Hook and E. Hemipholia F. Muell., Myrtaceae
【Usage】

Astringent.

Biomedical Effects and Toxicity

【Biological Activity】
Selective, ATP-competitive inhibitor of casein kinase 2 (CK2) (IC 50 values are 40, 2900, 3500, 4300 and 9400 nM for CK2, Lyn, PKA, Syk? and FGR respectively). Exhibits antioxidant, antitumor and anticarcinogenic activity and also inhibits glutathione S-transferase.
【Therapeutic Uses】
/EXPL THER/ Italian researchers found that ellagic acid seemed to reduce the side effects of chemotherapy in men with advanced prostate cancer, although it did not help slow disease progression or improve survival.
/EXPL THER/ Ellagic acid seems to have some anti-cancer properties. It can act as an antioxidant, and has been found to cause apoptosis (cell death) in cancer cells in the lab. In other lab studies, ellagic acid seems to reduce the effect of estrogen in promoting growth of breast cancer cells in tissue cultures. There are also reports that it may help the liver to break down or remove some cancer-causing substances from the blood. Some supporters have claimed these results mean that ellagic acid can prevent or treat cancer in humans. This has not been proven. Unfortunately, many substances showing promise against cancer in lab and animal studies have not been found to be useful in people. Ellagic acid has also been said to reduce heart disease, birth defects, liver problems, and to promote wound healing. The available scientific research does not support these claims at this time.
/EXPL THER/ ... Ellagic acid (EA) at a dose of 4 g/kg diet inhibited multiplicity of tumors induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in A/J mice by 54%. This inhibition was dose related between 0.06 and 4.0 g/kg diet ... [Boukharta M et al; Nutr Cancer 18(2):181-9 (1992)]
【Biomedical Effects and Toxicity】
The present study was initiated to determine ... the distribution of (14)C-ellagic acid (EA) and (3)H-N-methyl-N-nitrosourea (MNU) in the rat whole embryo culture model system ... (14)C-EA (50 uM for 2 hr, known embryoprotective concentration; no MNU added) was used to demonstrate access of EA to the embryo within the 2 hr exposure period. The majority of EA (99.5%) remained in the media while tissue concentrations of 57.0 and 47.9 pmol/mg were attained in the yolk sacs and embryos, respectively. [Frank AA et al; Teratology 47(4):275-80 (1993)] PubMed Abstract
Ellagic acid (EA), derived from fruit ellagitannins, is known to be antimutagenic and anticarcinogenic in various animal tumor models. In this study, EA at a dose of 4 g/kg diet inhibited multiplicity of tumors induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in A/J mice by 54%. This inhibition was dose related between 0.06 and 4.0 g/kg diet. In contrast, two related compounds, esculin and esculetin, had no effect on lung tumorigenesis. The biodistribution of ellagic acid (EA) /in A/J mice/ was studied as a function of dose and time after gavage of EA. The levels of EA in the lung were directly proportional to the dose of EA between 0.2 and 2.0 mmol. The maximum level of EA, corresponding to 21.3 nmol/g, was observed 30 minutes after gavage with 2.0 mmol of EA/kg body wt, which corresponds to only 70 ppm of the administered dose. The levels in liver tissues were 10-fold lower and reached a maximum 30 minutes after gavage. At this interval, the blood level of EA was 1 nmol/mL. The inclusion of EA in cyclodextrin doubles the level of EA in lung tissues. These results demonstrate that EA localizes preferentially in lung tissues ... [Boukharta M et al; Nutr Cancer 18(2):181-9 (1992)] PubMed Abstract
... Ellagic acid (EA), a dietary antioxidant associated with poor biopharmaceutical properties, was encapsulated into poly(lactide-co-glycolide) (PLGA) and polycaprolactone (PCL) nanoparticles to improve oral bioavailability ... The antioxidant potential of the didodecyldimethyl ammonium bromide (DMAB)-stabilized nanoparticulate formulations was evaluated against cyclosporine A (CyA)-induced nephrotoxicity in rats ... From in situ permeation studies in rats, it was evident that intestinal uptake of EA as DMAB-stabilized nanoparticles was significantly higher as compared to the sodium carboxymethyl cellulose suspension and the polyvinyl alcohol (PVA)-stabilized particles. EA and EA nanoparticles were able to prevent the CyA-induced nephrotoxicity in rats as evident by biochemical parameters as well as kidney histopathology. [Sonaje K et al; Pharm Res 24(5):899-908 (2007)] PubMed Abstract

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