digallic acid
m-galloylgallic acid
Identification
| Name | digallic acid |
| IUPAC | 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid |
| CAS Number | 536-08-3 |
| EINECS | 208-624-7 |
| FDA UNII | 404KO0584X |
| Molecular Formula | C14 H10 O9 |
| Molecular Weight | 322.22650000 |
| MDL Number | MFCD00068961 |
| Nikkaji Number | J6.349E |
| Beilstein | 2177723 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 269.00 °C. @ 760.00 mm Hg |
| Boiling Point | 727.80 °C. @ 760.00 mm Hg (est) |
| Flash Point | 532.00 °F. TCC ( 278.00 °C. ) (est) |
| logP (o/w) | 1.970 (est) |
| Soluble in | water, 500 mg/L @ 25 °C (exp) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | oral-rat LD50 2260 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for digallic acid usage levels up to | not for fragrance use. |
| Recommendation for digallic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
benzoic acid, 3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)- (9CI)
m-
digallic acid
meta-
digallic acid
3,4-
dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy) benzoic acid
3,4-
dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoic acid
3,4-
dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
gallic acid 3-gallate
gallic acid 3-monogallate
gallic acid, 3-gallate
3-
galloyl gallic acid
m-
galloyl gallic acid
m-
galloylgallic acid
PubMed:
Functional swapping between transmembrane proteins TMEM16A and TMEM16F.
PubMed:
Facile preparation of dehydrodigallic acid and its derivative for the synthesis of ellagitannins.
PubMed:
Expression and functional significance of the Ca(2+)-activated Cl(-) channel ANO6 in dendritic cells.
PubMed:
Investigation of the apoptotic way induced by digallic acid in human lymphoblastoid TK6 cells.
PubMed:
Digallate dimers of (-)-epigallocatechin gallate inactivate herpes simplex virus.
PubMed:
In vitro anti-uveal melanoma activity of phenolic compounds from the Egyptian medicinal plant Acacia nilotica.
PubMed:
Digallic acid from Pistascia lentiscus fruits induces apoptosis and enhances antioxidant activities.
PubMed:
ent-Eudesmane sesquiterpenoids, galloyl esters of the oak lactone precursor, and a 3-O-methylellagic acid glycoside from the wood of Platycarya strobilacea.
PubMed:
TMEM16A inhibitors reveal TMEM16A as a minor component of calcium-activated chloride channel conductance in airway and intestinal epithelial cells.
PubMed:
Inhibition of Ca2+-activated Cl- channels by gallotannins as a possible molecular basis for health benefits of red wine and green tea.
PubMed:
Hydrolysable tannins depress cardiac papillary muscle contraction and propranolol-induced negative inotropism.
PubMed:
Study of genotoxic, antigenotoxic and antioxidant activities of the digallic acid isolated from Pistacia lentiscus fruits.
PubMed:
Cytotoxic effects of digalloyl dimer procyanidins in human cancer cell lines.
PubMed:
Comparative analysis of phenolic acids in mistletoe plants from various hosts.
PubMed:
The interaction of polyphenols with bilayers: conditions for increasing bilayer adhesion.
PubMed:
Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase.
PubMed:
Increased adhesion between neutral lipid bilayers: interbilayer bridges formed by tannic acid.
PubMed:
[Chemical components of the leaves of Pistacia Chinensis Bge].
PubMed:
Differential inhibition of reverse transcriptase and various DNA polymerases by digallic acid and its derivatives.
PubMed:
Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by tannic acid, hydroxylated anthraquinones and hydroxylated cinnamic acid derivatives.
PubMed:
Fine structural analysis of the synaptic junction of Merkel cell-axon-complexes.
PubMed:
A biological synthesis of m-digallic acid.