gallic acid
3,4,5-trihydroxybenzoic zcid
 
Notes:
a colorless or slightly yellow crystalline compound obtained from nutgalls. it is used in photography, pharmaceuticals, and as an analytical reagent. Present in red wine. Japan approved food antioxidant additive Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3CO2H. Gallic acid is found both free and as part of tannins. It is commonly used in the pharmaceutical industry. Gallic acid can also be used to synthesize the hallucinogenic alkaloid mescaline, also known as 3,4,5-trimethoxyphenethylamine.; ; Salts and esters of gallic acid are termed gallates.; ; (Wikipedia).; Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3COOH. Gallic acid is found both free and as part of tannins. Salts and esters of gallic acid are termed gallates. Despite its name, it does not contain gallium.; Gallic acid was one of the substances used by Angelo Mai 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 damaging manuscripts for future study.[citation needed]
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      07-02600 GALLIC ACID ANHYDROUS
       
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3,4,5-trihydroxybenzoic acid (Click)
CAS Number: 149-91-7Picture of molecule
ECHA EINECS - REACH Pre-Reg: 205-749-9
FDA UNII: 632XD903SP
Nikkaji Web: J7.408J
Beilstein Number: 2050274
MDL: MFCD00002510
CoE Number: 10170
XlogP3: 0.70 (est)
Molecular Weight: 170.12082000
Formula: C7 H6 O5
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidants
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
Flavis Number: 08.080 (Old)
DG SANTE Food Flavourings: 08.080  gallic acid
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Physical Properties:
Appearance: white solid powder (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 242.00 °C. @ 760.00 mm Hg
Boiling Point: 501.00 °C. @ 760.00 mm Hg
Flash Point: 482.00 °F. TCC ( 250.00 °C. )
logP (o/w): 0.700
Soluble in:
 alcohol
 water, 11900 mg/L @ 20 °C (exp)
Insoluble in:
 water
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
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Suppliers:
Aceto
Gallic Acid
Coompo
For experimental / research use only.
Gallic Acid from Plants ≥96%
Odor: characteristic
Use: Antineoplastic agent, astringent. Possesses bacteriostatic activity. Gallic acid, a naturally occurring plant phenol with antioxidative activity, was found to induce cell death in promyelocytic leukemia HL-60RG cells, although many antioxidants are well known to protect the cell from oxidative stress. Morphological and biochemical studies indicated that the gallic acid-induced cell death is apoptosis. Flow cytometric analysis revealed that the apoptosis was not triggered at a specific phase of the cell cycle and that 2 h exposure of gallic acid to HL-60RG cells was enough to induce apoptosis. The inhibitory assay suggested that gallic acid-induced cell death was mediated by reactive oxygen species such as hydrogen peroxide, superoxide anion in addition to Ca2+ ion, calmodulin-dependent enzymes. Structure-activity analysis suggests that gallic acid induces apoptosis in HL-60RG cells, depending on its distinctive feature derived from the structure but not on its antioxidative activity. Gallic acid was found to possess anti-inflammatory activity towards zymosan-induced acute food pad swelling in mice. In vitro studies on the mode of action of gallic acid revealed that this compound interferes with the functioning of polymorphonuclear leukocytes (PMNs). Scavenging of superoxide anions, inhibition of myeloperoxidase release and activity as well as a possible interference with the assembly of active NADPH-oxidase may account for the inhibition of inflammatory process by gallic acid. Structure-activity relationship analysis showed that the o-dihydroxy group of gallic acid is important for the inhibitory activity in vitro.
EMD Millipore
For experimental / research use only.
Gallic Acid
ExtraSynthese
For experimental / research use only.
Gallic Acid (HPLC) ≥99%
Minasolve
MinaCare Galace Eco-cert (Gallic Acid)
Odor: characteristic
Use: The Gallic acid, extracted from gallnuts, is very widely used to manufacture propyl gallate, a well known anti-oxidant, used in the food industry.
Penta International
GALLIC ACID ANHYDROUS
Santa Cruz Biotechnology
For experimental / research use only.
Gallic Acid ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Gallic Acid 97.5-102.5% (titration)
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Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37 - Wear suitable protective clothing and gloves.
 
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:
gavage-rabbit LD50  5000 mg/kg
Dosed as a 10% solution.
(Dollahite et al., 1962)

oral-mouse LD50  [sex: M,F] > 5000 mg/kg
(Rajalakshsmi et al., 2001)

intravenous-mouse LD50  320 mg/kg
(Rajalakshsmi et al., 2001)

intraperitoneal-mouse LD50  4300 mg/kg
(Rajalakshsmi et al., 2001)

intraperitoneal-mouse LD50  4300 mg/kg
Pharmacology and Toxicology Vol. 64, Pg. 247, 1989.

intravenous-mouse LD50  320 mg/kg
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02597

oral-rabbit LD50  5000 mg/kg
KIDNEY, URETER, AND BLADDER: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LIVER: OTHER CHANGES
American Journal of Veterinary Research. Vol. 23, Pg. 1264, 1962.

Dermal Toxicity:
subcutaneous-rat LDLo 5000 mg/kg
Journal of Agricultural and Food Chemistry. Vol. 17, Pg. 497, 1969.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antioxidants
Recommendation for gallic acid usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.011 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 1600 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 3.0000015.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 2.0000010.00000
Edible ices, including sherbet and sorbet (03.0): 3.0000015.00000
Processed fruit (04.1): 2.0000010.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 4.0000020.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 2.0000010.00000
Bakery wares (07.0): 5.0000025.00000
Meat and meat products, including poultry and game (08.0): 1.000005.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 1.000005.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 2.0000010.00000
Foodstuffs intended for particular nutritional uses (13.0): 3.0000015.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 2.0000010.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 4.0000020.00000
Ready-to-eat savouries (15.0): 5.0000025.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 2.0000010.00000
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Safety References:
European Food Safety Athority(efsa): Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
European Food Safety Authority (EFSA) reference(s):
Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the Commission related to Flavouring Group Evaluation 20 (FGE.20): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical group 23
View page or View pdf
Flavouring Group Evaluation 52 (FGE.52): Consideration of hydroxy- and alkoxy-substituted benzyl derivatives evaluated by JECFA (57th meeting) structurally related to benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters evaluated by EFSA in FGE.20 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf
Flavouring Group Evaluation 54 (FGE.54)[1] - Consideration of benzyl derivatives evaluated by JECFA (57th meeting) structurally related to benzyl alcohols, benzaldehydes, a related acetal, benzoic acids and related esters evaluated by EFSA in FGE.20 (2005) - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf
Flavouring Group Evaluation 20, Revision 1 (FGE.20Rev1): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids and related esters from chemical group 23
View page or View pdf
Flavouring Group Evaluation 54, Revision 1 (FGE.54Rev1): Consideration of benzyl derivatives evaluated by JECFA (57th meeting) structurally related to benzyl alcohols, benzaldehydes, a related acetal, benzoic acids and related esters evaluated by EFSA in FGE.20Rev1 (2009)
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 20, Revision 2 (FGE.20Rev2): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 20, Revision 3(FGE.20Rev3): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 20, Revision 4 (FGE.20Rev4): Benzyl alcohols, benzaldehydes, a related acetal, benzoic acids, and related esters from chemical groups 23 and 30
View page or View pdf
EPI System: View
Daily Med: search
NIOSH International Chemical Safety Cards: search
NLM Hazardous Substances Data Bank: Search
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Carcinogenic Potency Database: Search
EPA GENetic TOXicology: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA Substance Registry Services (TSCA): 149-91-7
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 370
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 3,4,5-trihydroxybenzoic acid
Chemidplus: 0000149917
EPA/NOAA CAMEO: hazardous materials
RTECS: 149-91-7
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References:
 3,4,5-trihydroxybenzoic acid
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 149-91-7
Pubchem (cid): 370
Pubchem (sid): 134975594
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (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
Golm Metabolome Database: Search
Metabolomics Database: Search
UM BBD: Search
KEGG (GenomeNet): C01424
HMDB (The Human Metabolome Database): HMDB05807
FooDB: FDB000662
YMDB (Yeast Metabolome Database): YMDB01323
Export Tariff Code: 2918.29.3000
Haz-Map: View
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Formulations/Preparations:
•gallic acid, potassium chlorate & red gum (formula 156) is a pyrotechnic whistle composition. •available as the monohydrate
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 antioxidants 
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Occurrence (nature, food, other): note
 allspice
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 apple fruit
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 apple pericarp
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 beer - up to 0.6 mg/kg
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 bilberry fruit juice
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 bilberry leaf
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 blueberry plant
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 buckthorn sea buckthorn
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 carob bean
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 cashew nut
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 cherry - up to 7 mg/kg
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 cherry sour cherry plant
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 chestnut sweet chestnut leaf
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 clove bud
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 clove fruit
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 corn tissue culture
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 cough-grass
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 evening-primrose plant
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 grape
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 grape - up to 11 mg/kg
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 grape fruit
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 grape leaf
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 grape root
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 grape seed
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 guava fruit
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 guava heart wood
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 guava root
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 guava wood
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 jambul fruit
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 linden sapwood
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 mallow
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 mango flower
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 manilkara zapota cv.tikal
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 oak bark
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 olive fruit
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 oregano leaf
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 pomegranate fruit juice
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 pomegranate pericarp
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 potato root bark
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 raspberry red raspberry fruit
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 raspberry red raspberry juice
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 raspberry red raspberry leaf
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 raspberry red raspberry plant
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 rhubarb plant
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 rhubarb root
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 sage plant
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 soybean leaf
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 sumac
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 tarragon plant
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 tea leaf
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 tepescohuite
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 thyme plant
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 walnut black walnut nut
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 walnut english walnut fruit
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 walnut english walnut nut
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 whiskey - up to 6.1 mg/kg
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 wine - up to 35 mg/kg
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 witch hazel
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Synonyms:
 acid, gallic
 benzoic acid, 3,4,5-trihydroxy-
 gallic acid anhydrous
 pyrogallol-5-carboxylic acid
3,4,5-trihydroxy-benzoic acid
3,4,5-trihydroxybenzoic acid
3,4,5-trihydroxybenzoic acid, anhydrous
3,4,5-trihydroxybenzoic zcid
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Articles:
PubMed: In vitro free radical scavenging and DNA damage protective property of Coriandrum sativum L. leaves extract.
PubMed: Enhancement of antioxidant properties and increase of content of vitamin D2 and non-volatile components in fresh button mushroom, Agaricus bisporus (higher Basidiomycetes) by γ-irradiation.
PubMed: Flavored waters: influence of ingredients on antioxidant capacity and terpenoid profile by HS-SPME/GC-MS.
PubMed: Insulin secretagogue, alpha-glucosidase and antioxidant activity of some selected spices in streptozotocin-induced diabetic rats.
PubMed: Variation in phenolic composition and antioxidant activity during flower development of safflower (Carthamus tinctorius L.).
PubMed: Enhancement of fermentation process in Pu-erh tea by tea-leaf extract.
PubMed: Evaluation of antioxidant activity of green tea extract and its effect on the biscuits lipid fraction oxidative stability.
PubMed: Increase of theaflavin gallates and thearubigins by acceleration of catechin oxidation in a new fermented tea product obtained by the tea-rolling processing of loquat ( Eriobotrya japonica ) and green tea leaves.
PubMed: Identification and quantification of free radical scavengers in Pu-erh tea by HPLC-DAD-MS coupled online with 2,2'-Azinobis(3-ethylbenzthiazolinesulfonic acid) diammonium salt assay.
PubMed: Reactive oxygen scavenging activity of matured whiskey and its active polyphenols.
PubMed: Antioxidant activity of Egyptian Eucalyptus camaldulensis var. brevirostris leaf extracts.
PubMed: Effect of antioxidants on the quality of irradiated sausages prepared with turkey thigh meat.
PubMed: Lipid oxidation in fish oil enriched mayonnaise: calcium disodium ethylenediaminetetraacetate, but not gallic acid, strongly inhibited oxidative deterioration.
PubMed: Solid-state bioconversion of phenolics from cranberry pomace and role of Lentinus edodes beta-glucosidase.
PubMed: Study of interactions between food phenolics and aromatic flavors using one- and two-dimensional (1)H NMR spectroscopy.
PubMed: Tannins and human health: a review.
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