Gallic acid
|
|
| Names |
| IUPAC name
3,4,5-Trihydroxybenzoic acid
|
Other names
Gallic acid
Gallate
3,4,5-Trihydroxybenzoate |
| Identifiers |
|
CAS Number
|
149-91-7 Y
5995-86-8 (monohydrate) N |
| ChEBI |
CHEBI:30778 Y |
| ChEMBL |
ChEMBL288114 Y |
| ChemSpider |
361 Y |
| EC Number |
205-749-9 |
|
IUPHAR/BPS
|
5549 |
| Jmol interactive 3D |
Image |
| KEGG |
C01424 Y |
| PubChem |
370 |
| RTECS number |
LW7525000 |
| UNII |
632XD903SP Y |
InChI
-
InChI=1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12) Y
Key: LNTHITQWFMADLM-UHFFFAOYSA-N Y
-
InChI=1/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
Key: LNTHITQWFMADLM-UHFFFAOYAN
|
|
|
| Properties |
|
Chemical formula
|
C7H6O5 |
| Molar mass |
170.12 g/mol |
| Appearance |
White, yellowish-white, or
pale fawn-colored crystals. |
| Density |
1.694 g/cm3 (anhydrous) |
| Melting point |
260 °C (500 °F; 533 K) |
|
Solubility in water
|
1.19 g/100 mL, 20°C (anhydrous)
1.5 g/100 mL, 20 °C (monohydrate) |
| Solubility |
soluble in alcohol, ether, glycerol, acetone
negligible in benzene, chloroform, petroleum ether |
| log P |
0.70 |
| Acidity (pKa) |
COOH: 4.5, OH: 10. |
| Hazards |
| Main hazards |
Irritant |
| Safety data sheet |
External MSDS |
| NFPA 704 |
|
| Lethal dose or concentration (LD, LC): |
|
LD50 (Median dose)
|
5000 mg/kg (rabbit, oral) |
| Related compounds |
|
Related
|
phenols,
carboxylic acids |
|
Related compounds
|
Benzoic acid, Phenol, Pyrogallol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
| N verify (what is YN ?) |
| Infobox references |
|
|
Gallic acid is a trihydroxybenzoic acid, a type of phenolic acid, a type of organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants.[1] The chemical formula is C6H2(OH)3COOH. Gallic acid is found both free and as part of hydrolyzable tannins. The gallic acid groups are usually bonded to form dimers such as ellagic acid. Hydrolysable tannins break down on hydrolysis to give gallic acid and glucose or ellagic acid and glucose, known as gallotannins and ellagitannins respectively.[2]
Gallic acid forms intermolecular esters (depsides) such as digallic and trigallic acid, and cyclic ether-esters (depsidones).[3]
Gallic acid is commonly used in the pharmaceutical industry.[4] It is used as a standard for determining the phenol content of various analytes by the Folin-Ciocalteau assay; results are reported in gallic acid equivalents.[5] Gallic acid can also be used as a starting material in the synthesis of the psychedelic alkaloid mescaline.[6]
The name is derived from oak galls, which were historically used to prepare tannic acid. Despite the name, gallic acid does not contain gallium. Salts and esters of gallic acid are termed "gallates".
Contents
- 1 Historical context and uses
- 2 Metabolism
- 2.1 Biosynthesis
- 2.2 Degradation
- 2.3 Conjugation
- 3 Natural occurrences
- 4 Production
- 5 Sources
- 5.1 List of plants that contain gallic acid
- 5.2 In food
- 6 Spectral data
- 7 Esters
- 8 Health effects
- 9 Potential uses
- 10 See also
- 11 References
- 12 External links
Historical context and uses
Gallic acid is an important component of iron gall ink, the standard European writing and drawing ink from the 12th to 19th century with a history extending to the Roman empire and the Dead Sea Scrolls. Pliny the Elder (23-79 AD) describes his experiments with it and writes that it was used to produce dyes. Galls (also known as oak apples) from oak trees were crushed and mixed with water, producing tannic acid. It could then be mixed with green vitriol (ferrous sulfate) — obtained by allowing sulfate-saturated water from a spring or mine drainage to evaporate — and gum arabic from acacia trees; this combination of ingredients produced the ink.[7]
Gallic acid was one of the substances used by Angelo Mai (1782–1854), among other early investigators of palimpsests, to clear the top layer of text off and reveal hidden manuscripts underneath. Mai was the first to employ it, but did so "with a heavy hand", often rendering manuscripts too damaged for subsequent study by other researchers.[citation needed]
Gallic acid was first studied by the Swedish chemist Carl Wilhelm Scheele in 1786.[8] In 1818 the French chemist and pharmacist Henri Braconnot (1780–1855) devised a simpler method of purifying gallic acid from galls;[9] gallic acid was also studied by the French chemist Théophile-Jules Pelouze (1807–1867),[10] among others.
George Washington used gallic acid to communicate with spies[clarification needed] during the American Revolutionary War, according to the miniseries America: The Story of Us.[citation needed]
Gallic acid is a component of some pyrotechnic whistle mixtures.
Metabolism
Biosynthesis
Chemical structure of 3,5-didehydroshikimate
Gallic acid is formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate. This latter compound tautomerizes to form the redox equivalent gallic acid, where the equilibrium lies essentially entirely toward gallic acid because of the coincidentally occurring aromatization.[11][12]
Degradation
Gallate dioxygenase is an enzyme found in Pseudomonas putida that catalyses the reaction
- gallate + O2 → (1E)-4-oxobut-1-ene-1,2,4-tricarboxylate.
Gallate decarboxylase is another enzyme in the degradation of gallic acid.
Conjugation
Gallate 1-beta-glucosyltransferase is an enzyme that uses UDP-glucose and gallate, whereas its two products are UDP and 1-galloyl-beta-D-glucose.
Natural occurrences
Gallic acid is found in a number of land plants, such as the parasitic plant, Cynomorium coccineum,[13] the aquatic plant, Myriophyllum spicatum, and the blue-green alga, Microcystis aeruginosa.[14]
Production
Gallic acid is easily freed from gallotannins by acidic or alkaline hydrolysis. When gallic acid is heated with concentrated sulfuric acid, rufigallol is produced by condensation. Oxidation with arsenic acid, permanganate, persulfate, or iodine yields ellagic acid, as does reaction of methyl gallate with iron(III) chloride.[3]
Sources
List of plants that contain gallic acid
- Gallic acid is found in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur).[15]
- Caesalpinia mimosoides[16]
- stem bark of Boswellia dalzielii[17]
- Drosera (sundew)
- Rhodiola rosea (golden root)
- Triphala (Ayurvedic herbal rasayana formula)
- Toona sinensis
- Urtica dioica (stinging nettle)
- Humulus lupulus (common hop)
In food
- Areca nut
- Banana [18]
- Bearberry (Arctostaphylos sp)
- Bergenia sp
- Blackberry
- Black Tea [19]
- Green tea [18]
- Hot chocolate
- Juglans regia (Common walnut)
- Mango in peels and leaves
- Phyllanthus emblica (Indian gooseberry) in fruits
- Raspberry
- Strawberry
- Syzygium aromaticum (clove)[20]
- Vinegar[21]
- Wine grape seeds[22]
- Witch hazel (Hamamelis virginiana)
- White tea
Spectral data
| UV-Vis |
| Lambda-max: |
220, 271 nm (ethanol)
|
| Extinction coefficient (log ε) |
|
| IR |
| Major absorption bands |
ν : 3491, 3377, 1703, 1617, 1539, 1453, 1254 cm−1 (KBr) |
| NMR |
| Proton NMR
(acetone-d6):
d : doublet, dd : doublet of doublets,
m : multiplet, s : singlet
|
δ :
7.15 (2H, s, H-3 and H-7)
|
| Carbon-13 NMR
(acetone-d6):
|
δ :
167.39 (C-1),
144.94 (C-4 and C-6),
137.77 (C-5),
120.81 (C-2),
109.14 (C-3 and C-7)
|
| Other NMR data |
| MS |
Masses of
main fragments |
ESI-MS [M-H]- m/z : 169.0137 ms/ms (iontrap)@35 CE m/z product 125(100), 81(<1) |
Reference[16]
Esters
Also known as galloylated esters:
- Methyl gallate
- Ethyl gallate, a food additive with E number E313
- Propyl gallate, or propyl 3,4,5-trihydroxybenzoate, an ester formed by the condensation of gallic acid and propanol
- Octyl gallate, the ester of octanol and gallic acid
- Dodecyl gallate, or lauryl gallate, the ester of dodecanol and gallic acid
- Epicatechin gallate, a flavan-3-ol, a type of flavonoid, present in green tea
- Epigallocatechin gallate (EGCG), also known as epigallocatechin 3-gallate, the ester of epigallocatechin and gallic acid, and a type of catechin
- Gallocatechin gallate (GCG), the ester of gallocatechin and gallic acid and a type of flavan-3ol
- Theaflavin-3-gallate, a theaflavin derivative
Health effects
It is a weak carbonic anhydrase inhibitor.[23] In basic research, gallic acid extracted from grape seeds has been shown to inhibit the formation of amyloid fibrils, one of the potential causes of Alzheimer's disease and Parkinson's disease.[24][25][26] One study indicated that gallic acid has this effect on amyloid protein formation by modifying the properties of alpha-synuclein, a protein associated with the onset of neurodegenerative diseases.[26]
Gallic acid is classified as mutagen and teratogen.[3]
Potential uses
It can be used to produce polyesters based on phloretic acid and gallic acid.[27]
See also
- Hydrolyzable tannin
- Pyrogallol
- Syringol
- Syringaldehyde
- Syringic acid
- Shikimic acid
References
- ^ LD Reynolds and NG Wilson, "Scribes and Scholars" 3rd Ed. Oxford: 1991. pp193–4.
- ^ Andrew Pengelly (2004), The Constituents of Medicinal Plants (2nd ed.), Allen & Unwin, pp. 29–30
- ^ a b c Edwin Ritzer; Rudolf Sundermann (2007), "Hydroxycarboxylic Acids, Aromatic", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 6
- ^ Fiuza, S. M.; Gomes, C.; Teixeira, L. J.; Girão da Cruz, M. T.; Cordeiro, M. N. D. S.; Milhazes, N.; Borges, F.; Marques, M. P. M. "Phenolic acid derivatives with potential anticancer properties––a structure–activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids". Bioorganic & Medicinal Chemistry (Elsevier) 12 (13): 3581–3589. doi:10.1016/j.bmc.2004.04.026.
- ^ Andrew Waterhouse. "Folin-Ciocalteau Micro Method for Total Phenol in Wine". UC Davis.
- ^ Tsao, Makepeasce (July 1951). "A New Synthesis Of Mescaline". Journal of the American Chemical Society 73 (11): 5495–5496. doi:10.1021/ja01155a562. ISSN 0002-7863.
- ^ Fruen, Lois. "Iron Gall Ink".
- ^ Carl Wilhelm Scheele (1786) "Om Sal essentiale Gallarum eller Gallåple-salt" (On the essential salt of galls or gall-salt), Kongliga Vetenskaps Academiens nya Handlingar (Proceedings of the Royal [Swedish] Academy of Science), vol 7, pages 30-34.
- ^ Braconnot Henri (1818). "Observations sur la préparation et la purification de l'acide gallique, et sur l'existence d'un acide nouveau dans la noix de galle" [Observations on the preparation and purification of gallic acid, and on the existence of a new acid in galls]. Annales de chimie et de physique 9: 181–184.
- ^ J. Pelouze (1833) "Mémoire sur le tannin et les acides gallique, pyrogallique, ellagique et métagallique," Annales de chimie et de physique, vol. 54, pages 337-365 [presented February 17, 1834].
- ^ Gallic acid pathway on metacyc.org
- ^ Dewick, PM; Haslam, E (1969). "Phenol biosynthesis in higher plants. Gallic acid". Biochemical Journal 113 (3): 537–542. PMC 1184696. PMID 5807212.
- ^ Zucca, Paolo; Rosa, Antonella; Tuberoso, Carlo; Piras, Alessandra; Rinaldi, Andrea; Sanjust, Enrico; Dessì, Maria; Rescigno, Antonio (11 January 2013). "Evaluation of Antioxidant Potential of "Maltese Mushroom" (Cynomorium coccineum) by Means of Multiple Chemical and Biological Assays". Nutrients 5 (1): 149–161. doi:10.3390/nu5010149. PMC 3571642. PMID 23344249.
- ^ Nakai, S (2000). "Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae Microcystis aeruginosa". Water Research 34 (11): 3026–3032. doi:10.1016/S0043-1354(00)00039-7.
- ^ Mämmelä, Pirjo; Savolainen, Heikki; Lindroos, Lasse; Kangas, Juhani; Vartiainen, Terttu (2000). "Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry". Journal of Chromatography A 891 (1): 75–83. doi:10.1016/S0021-9673(00)00624-5. PMID 10999626.
- ^ a b Chanwitheesuk, Anchana; Teerawutgulrag, Aphiwat; Kilburn, Jeremy D.; Rakariyatham, Nuansri (2007). "Antimicrobial gallic acid from Caesalpinia mimosoides Lamk". Food Chemistry 100 (3): 1044–1048. doi:10.1016/j.foodchem.2005.11.008.
- ^ Alemika, Taiwo E.; Onawunmi, Grace O.; Olugbade, Tiwalade A. (2007). "Antibacterial phenolics from Boswellia dalzielii". Nigerian Journal of Natural Products and Medicine 10 (1): 108–10.
- ^ a b Pandurangan AK, Mohebali N, Norhaizan ME, Looi CY (2015). "Gallic acid attenuates dextran sulfate sodium-induced experimental colitis in BALB/c mice". Drug Design, Development and Therapy 9: 3923–34. doi:10.2147/DDDT.S86345. PMC 4524530. PMID 26251571.
- ^ Hodgson JM, Morton LW, Puddey IB, Beilin LJ, Croft KD (2000). "Gallic acid metabolites are markers of black tea intake in humans". Journal of Agricultural and Food Chemistry 48 (6): 2276–80. doi:10.1021/jf000089s. PMID 10888536.
- ^ Pathak, S. B.; Niranjan, K.; Padh, H.; Rajani, M.; et al. (2004). "TLC Densitometric Method for the Quantification of Eugenol and Gallic Acid in Clove". Chromatographia 60 (3–4): 241–244. doi:10.1365/s10337-004-0373-y.
- ^ Gálvez, Miguel Carrero; Barroso, Carmelo García; Pérez-Bustamante, Juan Antonio (1994). "Analysis of polyphenolic compounds of different vinegar samples". Zeitschrift für Lebensmittel-Untersuchung und -Forschung 199: 29–31. doi:10.1007/BF01192948.
- ^ Koyama, K; Goto-Yamamoto, N; Hashizume, K (2007). "Influence of maceration temperature in red wine vinification on extraction of phenolics from berry skins and seeds of grape (Vitis vinifera)". Bioscience, Biotechnology, and Biochemistry 71 (4): 958–65. doi:10.1271/bbb.60628. PMID 17420579.
- ^ Satomi, H; Umemura, K; Ueno, A; Hatano, T; Okuda, T; Noro, T (1993). "Carbonic anhydrase inhibitors from the pericarps of Punica granatum L". Biological & Pharmaceutical Bulletin 16 (8): 787–90. doi:10.1248/bpb.16.787. PMID 8220326.
- ^ Liu, Y; Pukala, T. L.; Musgrave, I. F.; Williams, D. M.; Dehle, F. C.; Carver, J. A. (2013). "Gallic acid is the major component of grape seed extract that inhibits amyloid fibril formation". Bioorganic & Medicinal Chemistry Letters 23 (23): 6336–40. doi:10.1016/j.bmcl.2013.09.071. PMID 24157371.
- ^ Wang, Y. J.; Thomas, P; Zhong, J. H.; Bi, F. F.; Kosaraju, S; Pollard, A; Fenech, M; Zhou, X. F. (2009). "Consumption of grape seed extract prevents amyloid-beta deposition and attenuates inflammation in brain of an Alzheimer's disease mouse". Neurotoxicity Research 15 (1): 3–14. doi:10.1007/s12640-009-9000-x. PMID 19384583.
- ^ a b Liu, Y; Carver, J. A.; Calabrese, A. N.; Pukala, T. L. (2014). "Gallic acid interacts with α-synuclein to prevent the structural collapse necessary for its aggregation". Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 1844 (9): 1481–1485. doi:10.1016/j.bbapap.2014.04.013. PMID 24769497.
- ^ Reina, Antonio; Gerken, Andreas; Zemann, Uwe; Kricheldorf, Hans R. (1999). "New polymer syntheses, 101. Liquid-crystalline hyperbranched and potentially biodegradable polyesters based on phloretic acid and gallic acid". Macromolecular Chemistry and Physics 200 (7): 1784–1791. doi:10.1002/(SICI)1521-3935(19990701)200:7<1784::AID-MACP1784>3.0.CO;2-B.
External links
- King's American Dispensatory (1898) entry on Gallic acid
|
Antioxidants
|
|
| Food antioxidants |
- 6-Hydroxymelatonin
- Acetyl-L-carnitine (ALCAR)
- Alpha-lipoic acid (ALA)
- Ascorbic acid (vitamin C)
- Carotenoids (vitamin A)
- Curcumin
- Edaravone
- Polyphenols
- Glutathione
- Hydroxytyrosol
- L-carnitine
- Ladostigil
- Melatonin
- Mofegiline
- N-Acetylcysteine (NAC)
- N-Acetylserotonin (NAS)
- Oleocanthal
- Oleuropein
- Rasagiline
- Resveratrol
- Selegiline
- Selenium
- Tocopherols (vitamin E)
- Tocotrienols (vitamin E)
- Tyrosol
- Ubiquinone (coenzyme Q)
- Uric acid
|
|
| Fuel antioxidants |
- Butylated hydroxytoluene
- 2,6-Di-tert-butylphenol
- 1,2-Diaminopropane
- 2,4-Dimethyl-6-tert-butylphenol
- Ethylenediamine
|
|
| Measurements |
- Folin method
- ORAC
- TEAC
- FRAP
|
|
|
Types of gallotannins
|
|
| Aglycones |
- Digallic acid
- Gallic acid
|
|
| Galloyl glucoses |
|
|
|
|
Digalloyl glucoses:
|
- 1,6-Digalloyl glucose
- 2,6-Digalloyl glucose
- 3,6-digalloyl glucose
|
|
|
Trigalloyl glucoses:
|
- 1,2,3-Trigalloyl glucose
- 1,2,3-tri-O-galloyl-β-D-glucose
- 1,2,6-Trigalloyl glucose / 1,3,6-Trigalloyl glucose
|
|
|
Tetragalloyl glucoses:
|
- 1,2,3,6-tetragalloylglucose
- 1,2,3,6-tetra-O-galloyl-β-D-glucose
- 1,2,4,6-Tetragalloyl glucose
- 1,2,4,6-tetra-O-galloyl-β-D-glucose
|
|
|
Pentagalloyl glucose:
|
- 1,2,3,4,6-Pentagalloyl-glucose
- 6-digalloyl-1,2,3-trigalloyl-glucose
|
|
|
other
|
- Hexagalloyl glucose
- Heptagalloyl glucose
- Octagalloyl glucose
- Nonagalloyl glucose
- Decagalloyl glucose
|
|
|
| Galloyl quinic acids |
|
Galloyl quinic acids:
|
- 3-O-Galloylquinic acid
- 4-O-Galloylquinic acid
- 5-O-Galloylquinic acid
|
|
|
Digalloyl quinic acids:
|
- 1,4-Di-O-galloylquinic acid
- 3,4-di-O-Galloylquinic acid
- 3,5-di-O-Galloylquinic acid
- 4,5-di-O-Galloylquinic acid
|
|
|
Trigalloyl quinic acids:
|
- 1,3,4-Tri-O-galloylquinic acid
- 3,4,5-Tri-O-galloylquinic acid
|
|
|
| Galloyl shikimic acids |
- 4-O-Galloyl shikimic acid
- 5-O-Galloyl shikimic acid
- 3,5-di-O-galloyl-shikimic acid
- 3,4,5-tri-O-galloylshikimic acid
|
|
| others |
- 1,2,6-trigalloyl alloside
- 1,3,6-trigalloyl alloside
- 1,2,3,6-tetragalloyl alloside
- 1-O-galloyl proto-quercitol
- 1,4-di-O-galloyl proto-quercitol
|
|
|
Phenolic acids (C6-C1) and their glycosides
|
|
| Monohydroxybenzoic acids |
- 3-Hydroxybenzoic acid
- 4-Hydroxybenzoic acid
- Salicylic acid (2-Hydroxybenzoic acid)
|
Glycosides
|
- p-Hydroxybenzoic acid glucoside
|
|
|
Acetylated
|
- Methylparaben (Methyl p-hydroxybenzoic acid)
|
|
|
| Dihydroxybenzoic acids |
- 2,3-Dihydroxybenzoic acid (Hypogallic acid)
- 2,4-Dihydroxybenzoic acid
- 2,5-Dihydroxybenzoic acid (Gentisic acid)
- 2,6-Dihydroxybenzoic acid
- 3,4-Dihydroxybenzoic acid (Protocatechuic acid)
- 3,5-Dihydroxybenzoic acid
|
Acetylated
|
- Ethyl protocatechuate
- Orsellinic acid
|
|
|
| Trihydroxybenzoic acids |
- Gallic acid
- Phloroglucinol carboxylic acid
|
Glycosides
|
- Bergenin
- Norbergenin
- Theogallin
- Chebulic acid
|
|
|
Acetylated
|
- Ethyl gallate
- Eudesmic acid
- Methyl gallate
- Syringic acid
|
|
|