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hippuric acid
2-(phenylformamido)acetic acid

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Name:2-benzamidoacetic acid
CAS Number: 495-69-2Picture of molecule3D/inchi
Other(deleted CASRN):140480-84-8
ECHA EINECS - REACH Pre-Reg:207-806-3
FDA UNII: TE0865N2ET
Nikkaji Web:J1.562H
Beilstein Number:1073987
MDL:MFCD00002692
XlogP3:0.30 (est)
Molecular Weight:179.17533000
Formula:C9 H9 N O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:cosmetic ingredient for hair conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "odor"Search
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: 191.50 °C. @ 760.00 mm Hg
Boiling Point: 464.12 °C. @ 760.00 mm Hg (est)
Flash Point: 454.00 °F. TCC ( 234.50 °C. ) (est)
logP (o/w): 0.310
Soluble in:
 water, 3750 mg/L @ 25 °C (exp)
 water, 3.021e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: hair conditioning
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Hippuric acid 98%
BOC Sciences
For experimental / research use only.
Hippuric acid 97%
Odor: characteristic
Use: N-Benzoylglycine also known as Hippuric Acid is the glycine conjugate of benzoic acid commonly found in ruminant
EMD Millipore
For experimental / research use only.
Hippuric Acid
Glentham Life Sciences
Hippuric acid
Penta International
HIPPURIC ACID
Sigma-Aldrich: Sigma
For experimental / research use only.
Hippuric acid 98%
 
Safety Information:
Preferred SDS: View
 
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:
intraperitoneal-rat LD50 1500 mg/kg
Bollettino Chimico Farmaceutico. Vol. 112, Pg. 53, 1973.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
cosmetic ingredient for hair conditioning
Recommendation for hippuric acid usage levels up to:
 not for fragrance use.
 
Recommendation for hippuric 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 Substance Registry Services (TSCA):495-69-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :464
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-benzamidoacetic acid
Chemidplus:0000495692
RTECS:MR8150000 for cas# 495-69-2
 
References:
 2-benzamidoacetic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):464
Pubchem (sid):134977187
 
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
KEGG (GenomeNet):C01586
HMDB (The Human Metabolome Database):HMDB00714
FooDB:FDB001819
Export Tariff Code:2924.29.4690
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
 avocado
Search Trop Picture
 cranberry fruit
Search Trop Picture
 
Synonyms:
 acetic acid, (benzoylamino)-
 benzamidoacetic acid
2-benzamidoacetic acid
 benzoylamino-acetic acid
(benzoylamino)-acetic acid
(benzoylamino)acetic acid
 benzoylaminoacetic acid
N-benzoylglycine
 glycine, N-benzoyl-
 hippuricacid
N-(phenylcarbonyl)glycine
2-(phenylcarbonylamino)acetic acid
 phenylcarbonylaminoacetic acid
2-(phenylformamido)acetic acid
 

Articles:

PubMed:Hippuric acid in 24 h urine collections as a biomarker of fruits and vegetables intake in kidney stone formers.
PubMed:The role of sodium in the salty taste of permeate.
PubMed:Hydrophilic interaction chromatography-mass spectrometry for anionic metabolic profiling of urine from antibiotic-treated rats.
PubMed:Disintegration of wheat aleurone structure has an impact on the bioavailability of phenolic compounds and other phytochemicals as evidenced by altered urinary metabolite profile of diet-induced obese mice.
PubMed:Metabonomic analysis of quercetin against the toxicity of chronic exposure to low-level dichlorvos in rats via ultra-performance liquid chromatography-mass spectrometry.
PubMed:Effect of uremic serum and uremic toxins on drug metabolism in human microsomes.
PubMed:ACE-inhibitory activity of enzymatic protein hydrolysates from lupin and other legumes.
PubMed:Decomposition pathways and rates of human urine in soils.
PubMed:Metabolic profiling of phenolic acids and oxidative stress markers after consumption of Lonicera caerulea L. fruit.
PubMed:Application of ultraperformance liquid chromatography/mass spectrometry-based metabonomic techniques to analyze the joint toxic action of long-term low-level exposure to a mixture of organophosphate pesticides on rat urine profile.
PubMed:Identification of novel dietary phytochemicals inhibiting the efflux transporter breast cancer resistance protein (BCRP/ABCG2).
PubMed:1H NMR-based metabolic fingerprinting of urine metabolites after consumption of lingonberries (Vaccinium vitis-idaea) with a high-fat meal.
PubMed:Phenolic acid concentrations in plasma and urine from men consuming green or black tea and potential chemopreventive properties for colon cancer.
PubMed:Metabolic influence of acute cyadox exposure on Kunming mice.
PubMed:Blanching improves anthocyanin absorption from highbush blueberry ( Vaccinium corymbosum L.) purée in healthy human volunteers: a pilot study.
PubMed:Rapid and simple colorimetric assay for screening angiotensin I-converting enzyme inhibitors.
PubMed:Hippuric acid in 24-hour urine collections is a potential biomarker for fruit and vegetable consumption in healthy children and adolescents.
PubMed:Urinary excretion and metabolism of procyanidins in pigs.
PubMed:Authentication of beef production systems using a metabolomic-based approach.
PubMed:Consumption of Hibiscus sabdariffa L. aqueous extract and its impact on systemic antioxidant potential in healthy subjects.
PubMed:Dynamic metabolic response of mice to acute mequindox exposure.
PubMed:In vitro anti-platelet effects of simple plant-derived phenolic compounds are only found at high, non-physiological concentrations.
PubMed:Screening assay of angiotensin-converting enzyme inhibitory activity from complex natural colourants and foods using high-throughput LC-MS/MS.
PubMed:Differentiation of organic goat's milk based on its hippuric acid content as determined by capillary electrophoresis.
PubMed:Long-term effects of three commercial cranberry products on the antioxidative status in rats: a pilot study.
PubMed:Urinary excretion of phenolic acids in rats fed cranberry.
PubMed:Anthocyanin absorption, metabolism, and distribution from a wild blueberry-enriched diet (Vaccinium angustifolium) is affected by diet duration in the Sprague-Dawley rat.
PubMed:The metabolic fate of red wine and grape juice polyphenols in humans assessed by metabolomics.
PubMed:Moderate Champagne consumption promotes an acute improvement in acute endothelial-independent vascular function in healthy human volunteers.
PubMed:Colorimetric, high-throughput assay for screening Angiotensin I-converting enzyme inhibitors.
PubMed:Bioavailability of [2-(14)C]quercetin-4'-glucoside in rats.
PubMed:Diclofenac toxicity in Gyps vulture is associated with decreased uric acid excretion and not renal portal vasoconstriction.
PubMed:Transepithelial transport and stability in blood serum of angiotensin-I-converting enzyme inhibitory dipeptides.
PubMed:Urinary hippuric acid after ingestion of edible fruits.
PubMed:Sorghum bran in the diet dose dependently increased the excretion of catechins and microbial-derived phenolic acids in female rats.
PubMed:Assay of angiotensin I-converting enzyme-inhibiting activity based on the detection of 3-hydroxybutyric acid.
PubMed:Biosafety, antioxidant status, and metabolites in urine after consumption of dried cranberry juice in healthy women: a pilot double-blind placebo-controlled trial.
PubMed:An NMR-based metabonomic investigation on effects of milk and meat protein diets given to 8-year-old boys.
PubMed:Influence of benzoic acid and dietary protein level on performance, nitrogen metabolism and urinary pH in growing-finishing pigs.
PubMed:Metabonomics approach to determine metabolic differences between green tea and black tea consumption.
PubMed:Mechanisms and biomarkers of cardiovascular injury induced by phosphodiesterase inhibitor III SK&F 95654 in the spontaneously hypertensive rat.
PubMed:Performance of two commonly used angiotensin-converting enzyme inhibition assays using FA-PGG and HHL as substrates.
PubMed:Nuclear magnetic resonance spectroscopic based studies of the metabolism of black tea polyphenols in humans.
PubMed:Direct spectrophotometric measurement of angiotensin I-converting enzyme inhibitory activity for screening bioactive peptides.
PubMed:A metabonomic strategy for the detection of the metabolic effects of chamomile (Matricaria recutita L.) ingestion.
PubMed:Consumption of both black tea and green tea results in an increase in the excretion of hippuric acid into urine.
PubMed:Toxicology and carcinogenesis studies of microencapsulated trans-cinnamaldehyde in rats and mice.
PubMed:Molecular and ultrastructural characterization of porcine hippurate-negative Brachyspira pilosicoli.
PubMed:Peptides with angiotensin I-converting enzyme (ACE) inhibitory activity from defibrinated, hydrolyzed bovine plasma.
PubMed:Improved method for direct high-performance liquid chromatography assay of angiotensin-converting enzyme-catalyzed reactions.
PubMed:Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans.
PubMed:Final report on the safety assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate.
PubMed:Evaluation of commercial immunoassays for cross-reactivity to clenbuterol stereoisomers and bovine metabolites.
PubMed:Analysis of neurotoxin 3-N-oxalyl-L-2,3-diaminopropionic acid and its alpha-isomer in Lathyrus sativus by high-performance liquid chromatography with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) derivatization.
PubMed:Hippuric acid as a major excretion product associated with black tea consumption.
PubMed:Metabolism of n-butyl benzyl phthalate in the female Wistar rat. Identification of new metabolites.
PubMed:Evaluation of potential disinfectants for preslaughter broiler crop decontamination.
PubMed:Pharmacokinetics and metabolism of [14C]dichloroacetate in male Sprague-Dawley rats. Identification of glycine conjugates, including hippurate, as urinary metabolites of dichloroacetate.
PubMed:A surgical model for determination of true absorption and biliary excretion of manganese in conscious swine fed commercial diets.
PubMed:Excretion of benzoic acid derivatives in urine of sheep given intraruminal infusions of 3-phenylpropionic and cyclohexanecarboxylic acids.
PubMed:Cutaneous xenobiotic metabolism: glycine conjugation in human and rat keratinocytes.
PubMed:Use of in vitro skin penetration data and a physiologically based model to predict in vivo blood levels of benzoic acid.
PubMed:Factors affecting the metabolism of cinnamyl anthranilate in the rat and mouse.
PubMed:Metabolites of N-ethylbenzamide, N,N-diethylbenzamide and related compounds detected in rat urine by NMR spectroscopy.
PubMed:Use of nuclear magnetic resonance spectroscopy and selective C-labeling for pharmacokinetic research in man: detection of benzoic acid conversion to hippuric acid.
PubMed:Short-term inhalation toxicity of methanol, gasoline, and methanol/gasoline in the rat.
PubMed:Effects of gavage versus dosed feed administration on the toxicokinetics of benzyl acetate in rats and mice.
PubMed:Metabolism of trans-cinnamic acid in the rat and the mouse and its variation with dose.
PubMed:Studies on trans-cinnamaldehyde. 1. The influence of dose size and sex on its disposition in the rat and mouse.
PubMed:Dietary sources and background levels of hippuric acid in urine: comparison of Philippine and Japanese levels.
PubMed:Liver blood flow and metabolic clearance rate of progesterone in sheep.
PubMed:Tissue distribution and excretion of 14C-labelled cinnamic aldehyde following single and multiple oral administration in male Fischer 344 rats.
PubMed:Toxicokinetics of cinnamaldehyde in F344 rats.
PubMed:The influence of insulin and amino acid supply on amino acid uptake by the lactating bovine mammary gland.
PubMed:In vitro skin absorption and metabolism of benzoic acid, p-aminobenzoic acid, and benzocaine in the hairless guinea pig.
PubMed:Bioavailability, metabolism, and renal excretion of benzoic acid in the channel catfish (Ictalurus punctatus).
PubMed:Liver function in protein-energy malnutrition measured by cinnamic acid tolerance and benzoic acid tolerance: effect of carnitine supplementation.
PubMed:Studies on benzyl acetate. III. The percutaneous absorption and disposition of [methylene-14C]benzyl acetate in the rat.
PubMed:Studies on benzyl acetate. I. Effect of dose size and vehicle on the plasma pharmacokinetics and metabolism of [methylene-14C]benzyl acetate in the rat.
PubMed:[Mediator concepts and modulation of renal compensatory adaptation].
PubMed:Influence of dose and sex on the disposition and hepatic effects of cinnamyl anthranilate in the B6C3F1 mouse.
PubMed:Evaluation of the dose response and in utero exposure to saccharin in the rat.
PubMed:The effects of high dietary levels of sodium saccharin on mineral and water balance and related parameters in rats.
PubMed:Drugs, food additives and natural products as promoters in rat urinary bladder carcinogenesis.
PubMed:Urinary excretion of hippuric acid and o-cresol after laboratory exposure of humans to toluene.
PubMed:Exposure to toluene: uptake, distribution and elimination in man.
PubMed:[Physiopathological effects of feeding heated oils to rats].
PubMed:[Urinary excretion of glucuronic and hippuric acids in rats ingesting heated linseed oil].
PubMed:The effects of solid food and of alcoholic beverages, especially wine, on the excretion of hippuric acid.
 
Notes:
Hippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid found in the urine of horses and other herbivores. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C and decompose at about 240 °C. High concentrations of hippuric acid can also indicate a toluene intoxication. When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine.; Hippuric acid is an acyl glycine formed by the conjugation of benzoic aicd with glycine. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted to benzoic acid which is then converted to hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized to aromatic compounds including ortho-cresol, which is not found significantly in the urine of nonexposed individuals. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air.; Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. (PMID: 9120876, 8734460)
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