ortho-anthranilic acid
benzoic acid, 2-amino-
 
Notes:
2-Aminobenzoic acid is an organic compound. It is a substrate of enzyme anthranilate hydroxylase [EC 1.14.13.35] in benzoate degradation via hydroxylation pathway (KEGG). [HMDB]
  • BOC Sciences
    • BOC Sciences
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      Product(s):
      118-92-3 2-Aminobenzoic acid ≥98%
       
  • Glentham Life Sciences
  • TCI AMERICA
    • TCI AMERICA
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      Product(s):
      A0497 Anthranilic Acid >99.0%(HPLC)(T)
       
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CAS Number: 118-92-3Picture of molecule3D/inchi
Other(deleted CASRN): 80206-34-4
ECHA EINECS - REACH Pre-Reg: 204-287-5
FDA UNII: 0YS975XI6W
Nikkaji Web: J2.912B
Beilstein Number: 0471803
MDL: MFCD00007712
XlogP3: 1.20 (est)
Molecular Weight: 137.13819000
Formula: C7 H7 N O2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Appearance: white to pale yellow crystalline powder (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 145.00 °C. @ 760.00 mm Hg
Boiling Point: 311.89 °C. @ 760.00 mm Hg (est)
Flash Point: 288.00 °F. TCC ( 142.40 °C. ) (est)
logP (o/w): 1.210
Soluble in:
 water, 3500 mg/L @ 20 °C (exp)
 water, 7970 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
2-Aminobenzoic acid ≥98%
EMD Millipore
For experimental / research use only.
Anthranilic Acid
Glentham Life Sciences
Anthranilic acid
Sigma-Aldrich
For experimental / research use only.
Anthranilic acid
TCI AMERICA
For experimental / research use only.
Anthranilic Acid >99.0%(HPLC)(T)
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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-bird - wild LD50  750 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

unreported-mammal (species unspecified) LD50  6310 mg/kg
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(6), Pg. 22, 1983.

intraperitoneal-mouse LD50  2500 mg/kg
Russian Pharmacology and Toxicology Vol. 37, Pg. 105, 1974.

intravenous-mouse LD50  > 500 mg/kg
Yakugaku Zasshi. Journal of Pharmacy. Vol. 89, Pg. 1392, 1990.

oral-mouse LD50  1400 mg/kg
Quarterly Journal of Pharmacy & Pharmacology. Vol. 19, Pg. 483, 1946.

oral-rat LD50  5410 mg/kg
BEHAVIORAL: EXCITEMENT BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 27(3), Pg. 52, 1983.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for ortho-anthranilic acid usage levels up to:
 not for fragrance use.
 
Recommendation for ortho-anthranilic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
NIOSH International Chemical Safety Cards: search
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Carcinogenic Potency Database: Search
EPA Substance Registry Services (TSCA): 118-92-3
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 227
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 1
 2-aminobenzoic acid
Chemidplus: 0000118923
EPA/NOAA CAMEO: hazardous materials
RTECS: 118-92-3
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References:
 2-aminobenzoic acid
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 118-92-3
Pubchem (cid): 227
Pubchem (sid): 134974040
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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
Golm Metabolome Database: Search
Metabolomics Database: Search
UM BBD: Search
KEGG (GenomeNet): C00108
HMDB (The Human Metabolome Database): HMDB01123
FooDB: FDB000896
YMDB (Yeast Metabolome Database): YMDB00278
Export Tariff Code: 2922.49.3500
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
Formulations/Preparations:
grades: technical (95-98%); 99% or better.
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 wallflowerFR
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Occurrence (nature, food, other): note
 corn leaf
Search Trop  Picture
 jasmin
Search  PMC Picture
 mandarin
Search Trop  Picture
 neroli
Search  PMC Picture
 petitgrain
Search Trop  Picture
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Synonyms:
ortho-amidobenzoic acid
2-amino benzoic acid
1-amino-2-carboxybenzene
2-amino-benzoic acid
o-amino-benzoic acid
2-aminobenzoic acid
o-aminobenzoic acid
ortho-aminobenzoic acid
 anthranic acid
 anthranilic acid
o-anthranilic acid
 benzoic acid, 2-amino-
 benzoic acid, o-amino-
 carboxyaniline
2-carboxyaniline
 vitamin L
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Articles:
Google Patents: Manufacture of anthranilic acid
PubMed: Effects of sodium benzoate, a widely used food preservative, on glucose homeostasis and metabolic profiles in humans.
PubMed: A fluorescence-based method for cyanate analysis in ethanol/water media: correlation between cyanate presence and ethyl carbamate formation in sugar cane spirit.
PubMed: Inhibition of proliferative responses of lymphocytes to food antigens by an anti-allergic drug, N(3',4'-dimethoxycinnamoyl) anthranilic acid (Tranilast) in children with atopic dermatitis.
PubMed: Characterisation of odorant compounds and their biochemical formation in green tea with a low temperature storage process.
PubMed: Accumulation of anthranilic acid and N-glucosylanthranilic acid by a Corynebacterium glutamicum mutant resistant to DL-serine hydroxamate.
PubMed: Large amounts of picolinic acid are lethal but small amounts increase the conversion of tryptophan-nicotinamide in rats.
PubMed: Improved determination of milk oligosaccharides using a single derivatization with anthranilic acid and separation by reversed-phase high-performance liquid chromatography.
PubMed: Supplementing healthy women with up to 5.0 g/d of L-tryptophan has no adverse effects.
PubMed: Tryptophan catabolism and vitamin B-6 status are affected by gender and lifestyle factors in healthy young adults.
PubMed: Associations between intake of fish and n-3 long-chain polyunsaturated fatty acids and plasma metabolites related to the kynurenine pathway in patients with coronary artery disease.
PubMed: A mathematical model of tryptophan metabolism via the kynurenine pathway provides insights into the effects of vitamin B-6 deficiency, tryptophan loading, and induction of tryptophan 2,3-dioxygenase on tryptophan metabolites.
PubMed: 2-Pyridylfuran: a new fluorescent tag for the analysis of carbohydrates.
PubMed: Urinary excretory ratio of anthranilic acid/kynurenic acid as an index of the tolerable amount of tryptophan.
PubMed: Pyridoxine supplementation does not alter in vivo kinetics of one-carbon metabolism but modifies patterns of one-carbon and tryptophan metabolites in vitamin B-6-insufficient oral contraceptive users.
PubMed: The metabolites in the tryptophan degradation pathway might be useful to determine the tolerable upper intake level of tryptophan intake in rats.
PubMed: Pantothenic acid deficiency may increase the urinary excretion of 2-oxo acids and nicotinamide catabolites in rats.
PubMed: Fate of dietary tryptophan in young Japanese women.
PubMed: Quantification and characterization of enzymatically produced hyaluronan with fluorophore-assisted carbohydrate electrophoresis.
PubMed: Inhibition of interferon-gamma and interleukin-2 production from lymphocytes stimulated with food antigens by an anti-allergic drug, Tranilast, in patients with food-sensitive atopic dermatitis.
PubMed: Determination of methyl anthranilate in food samples by coupling stopped-flow mixing technique and time-resolved luminescence detection.
PubMed: Microwave assisted synthesis of 2,2'-arylene-substituted bis(4H-3,1-benzoxazin-4-one) derivatives using the complex cyanuric chloride/N,N-dimethylformamide.
PubMed: Evidence for significantly enhancing reduction of Azo dyes in Escherichia coli by expressed cytoplasmic Azoreductase (AzoA) of Enterococcus faecalis.
PubMed: Synthesis and insecticidal activities of novel anthranilic diamides containing acylthiourea and acylurea.
PubMed: Metabolism of azo dyes by human skin microbiota.
PubMed: Determination of sialyl and neutral oligosaccharide levels in transition and mature milks of Samoan women, using anthranilic derivatization followed by reverse phase high performance liquid chromatography.
PubMed: Effects of commercial processing on levels of antioxidants in oats (Avena sativa L.).
PubMed: Tryptophan catabolism in Brevibacterium linens as a potential cheese flavor adjunct.
PubMed: Structural characterization of N-linked oligosaccharides of laminin from rat kidney: changes during diabetes and modulation by dietary fiber and butyric acid.
PubMed: [Etiology of bladder cancer].
PubMed: Non-steroidal anti-inflammatory analgesics other than salicylates.
PubMed: In vitro antioxidant activity and antigenotoxic effects of avenanthramides and related compounds.
PubMed: Effect of nicotinamide administration on the tryptophan-nicotinamide pathway in humans.
PubMed: Influence of dose and sex on the disposition and hepatic effects of cinnamyl anthranilate in the B6C3F1 mouse.
PubMed: New potent DPPH radical scavengers from a marine-derived actinomycete strain USF-TC31.
PubMed: The historical aspects of sunscreens.
PubMed: Cinnamyl anthranilate causes coinduction of hepatic microsomal and peroxisomal enzymes in mouse but not rat.
PubMed: Cell action mechanism of tranilast--effect on the expression of HLA-class II antigen.
PubMed: Structural determination of hypnosin, a spore germination inhibitor of phytopathogenic Streptomyces sp. causing root tumor in melon (Cucumis sp.).
PubMed: FaGT2: a multifunctional enzyme from strawberry (Fragaria x ananassa) fruits involved in the metabolism of natural and xenobiotic compounds.
PubMed: The effects of phthalate esters on the tryptophan-niacin metabolism.
PubMed: Increase in conversion of tryptophan to niacin in pregnant rats.
PubMed: Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships.
PubMed: Tryptanthrins and other tryptophan-derived agonists of the dioxin receptor.
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