Ellagic acid - dilactone of hexahydroxydiphenic acid, refers to low molecular weight phenolic compounds , belongs to phenolcarboxylic acids . In bound form, it is a component of ellagotanins - tannins of the hydrolyzable group.
Ellagic acid | |
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Are common | |
| Systematic name | 2,3,7,8-tetrahydroxy [1] benzopyrano [5,4,3-cde] [1] benzopyran-5,10-dione |
| Chem. formula | C₁₄H₆O₈ |
| Rat formula | C 14 H 6 O 8 ! - rational formula (displays the structure of the substance) -> |
Physical properties | |
| Molar mass | 302.193 g / mol |
| Density | 1,667 g / cm³ |
Thermal properties | |
| T. melt. | 450 ℃ (with decomposition) |
Chemical properties | |
| Solubility in water | <0.1 g / 100 ml |
| Solubility in 1 M NaOH | 1 g / 100 ml |
Classification | |
| CAS Number | |
| PubChem | |
| ChemSpider | |
| EINECS Number | 207-508-3 |
| Chebi | 4775 |
| Drugbank | |
Smiles | |
C1 = C2C3 = C (C (= C1O) O) OC (= O) C4 = CC (= C (C (= C43) OC2 = O) O) O | |
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 | |
Security | |
| R phrases | R36 / 37/38 |
| S-phrases | S26 , S37 |
| H phrases | H315 , H319 , H335 |
| P-phrases | P261 , P305 + P351 + P338 , P302 + P352 , P321 , P405 , P501 |
| GHS icons |  |
| Data is provided for standard conditions (25 ℃, 100 kPa) , unless otherwise indicated. | |
Distribution
It is found in more than 700 species of higher plants. Practically not found in the Coniferous and Fern- shaped departments, in the Monocotyledonous class. The presence in plants may have taxonomic significance, for example, in the family Rosaceae is found only in plants of the subfamily Pink [1] .
Possible plant sources of production may be plants of the genus alder , birch , walnut , chestnut , oak [1] .
Production and biosynthesis
Gallic acid methyl ester in a solution of ammonia self-oxidizes to hexahydroxydiphenic acid, which, as a result of intramolecular transesterification, turns into ellagic acid [2] .
In nature, ellagic acid is similarly synthesized from corinagin tannin . Ellagic acid can also be formed due to aerobic oxidation of hebulinic acid or hydrolysis of hebulagic acid [1] .
It is formed when brewing Puer tea as a result of pyrolysis of strictinin ( English Strictinin ) along with gallic acid [3] .
Biological properties and application
Ellagic acid has pronounced cardioprotective activity. So, at a dose of 0.5 and 1 mg / kg, it exceeds the effectiveness of vitamin E at a dose of 50 mg / kg [1] .
Ellagic acid has a hypotensive effect, has antioxidant activity (per person), and plays a role in the mechanism of the inflammatory reaction. Also found its antitumor, antimutagenic, anticarcinogenic, enzyme inhibitory and reparative activity [1] .
Like other phenolic compounds, ellagic acid is a potential toxin that can inhibit the growth of pathogenic fungi and the multiplication of viruses in the macroorganism. There is evidence of an increase in the concentration of ellagic acid in some fungal infections of plants [1] .
In an individual state, it is characterized by low solubility in conventional solvents and even in such universal ones as pyridine and dimethyl sulfoxide , which to some extent interferes with its use in medicine, however, methods have been proposed for preparing its water-soluble derivatives (the formation of salts with alkalis, amino acids, etc.) [1 ] .
Based on ellagic acid and its derivatives, cosmetics for external use with whitening and photoprotective effects have been developed [1] .
Literature
- Hvorost, O. P. Ellagic acid, prevalence in the plant world and aspects of biological action / O. P. Hvorost, V. V. Maly, A. G. Serbin ... [et al. ] // Pharmacist: Journal .. - 1998. - Issue. 22. - S. 36−37.
- Fizer, Louis. Organic chemistry. Advanced course = Advanced organic chemistry: [trans. from English ]: in 2 t. / Louis Fizer, Mary Fizer. - M .: Chemistry, 1966. - T. 2. - 15 000 copies.
Notes
- ↑ 1 2 3 4 5 6 7 8 Brushwood et al., 1998 .
- ↑ Fizer, 1966 , p. 347.
- ↑ Chen, GH Significant elevation of antiviral activity of strictinin from Pu'er tea after thermal degradation to ellagic acid and gallic acid: [ eng. ] / GH Chen, YL Lin, WL Hsu ... [ et al. ] // Journal of Food and drug analysis. - 2015. - Vol. 23, no. 1 (March). - P. 116−123. - DOI : 10.1016 / j.jfda.2014.07.07.007 . - PMID 28911434 .