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digallic acid
m-galloylgallic acid

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Name:3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
CAS Number: 536-08-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-624-7
FDA UNII: 404KO0584X
Nikkaji Web:J6.349E
Beilstein Number:2177723
MDL:MFCD00068961
XlogP3-AA:1.10 (est)
Molecular Weight:322.22650000
Formula:C14 H10 O9
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 water, 5365 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Digallic acid ≥97%
Odor: characteristic
Use: Digallic acid is a natural polyphenolic that can be produced by hydrolysis of gallotannins. Digallic acid has antioxidant activ
Carbosynth
For experimental / research use only.
Digallic Acid
Santa Cruz Biotechnology
For experimental / research use only.
Digallic Acid
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 2260 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Canadian Medical Association Journal. Vol. 92, Pg. 1292, 1965.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :341
National Institute of Allergy and Infectious Diseases:Data
3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
Chemidplus:0000536083
 
References:
 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):341
Pubchem (sid):134977610
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C01572
HMDB (The Human Metabolome Database):Search
FooDB:FDB000229
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 evening-primrose leaf
Search Trop Picture
 mastic fruit
Search Trop Picture
 tea leaf
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
Digallic acid is a polyphenolic compound found in Pistacia lentiscus. Digallic acid is also present in the molecule of tannic acid. Digalloyl esters involve either -meta or -para depside bonds. [Wikipedia]
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