methyl anthranilate
grape enhancer - methyl anthranilate and phenethyl alcohol.
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Fragrance Demo Formulas    Flavor Demo Formulas
methyl 2-aminobenzoate (Click)
CAS Number: 134-20-3
ECHA EINECS - REACH Pre-Reg: 205-132-4
Beilstein Number: 0606965
MDL: MFCD00007710
FEMA Number: 2682
CoE Number: 250
XlogP3: 1.90 (est)
Molecular Weight: 151.16513000
Formula: C8 H9 N O2
BioActivity Summary: listing
NMR Predictor: Predict
Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
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Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
Read: Under the conditions of intended use - New developments in the FEMA GRAS program and the safety assessment of flavor ingredients
Read: A GRAS assessment program for flavor ingredients
Read: Sensory testing for flavorings with modifying properties. Food Technology
Read: Criteria for the safety evaluation of flavoring substances
Read: A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils
Read: FEMA Expert Panel: 30 Years of safety evaluation for the flavor industry
Read: Consumption ratio and food predominance of flavoring materials
JECFA Food Flavoring: 1534  methyl anthranilate
Flavis Number: 09.715 (Old)
EU SANCO Food Flavourings: 09.715  methyl anthranilate

FEMA Number: 2682  methyl anthranilate
FDA Regulation:
Subpart A--General Provisions
Sec. 182.60 Synthetic flavoring substances and adjuvants.
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Physical Properties:
Appearance: pale yellow to dark yellow clear liquid to solid (est)
Assay: 99.00 to 100.00 % 
Food Chemicals Codex Listed: Yes
Specific Gravity: 1.16100 to 1.16900 @  25.00 °C.
Pounds per Gallon - (est).: 9.661 to  9.727
Melting Point: 23.00 to  24.50 °C. @ 760.00 mm Hg
Boiling Point: 238.00 to  241.00 °C. @ 760.00 mm Hg
Boiling Point: 163.00 to  164.00 °C. @ 50.00 mm Hg
Congealing Point: 23.80 °C.
Saponification Value: 98.00 to 102.00
Vapor Pressure: 0.016000 mm/Hg @ 25.00 °C. (est)
Vapor Density: 5.2 ( Air = 1 )
Flash Point: 200.00 °F. TCC ( 93.33 °C. )
logP (o/w): 1.880
Shelf Life: 12.00 month(s) or longer if stored properly.
Storage: store in cool, dry place in tightly sealed containers, protected from heat and light.
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Organoleptic Properties:
Odor Type: fruity
Odor Strength: medium
Odor Description:
at 100.00 %. 
fruity grape orangeflower neroli
Substantivity: 88 Hour(s)
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: masking agents
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Safety Information:
Most important hazard(s):
Xi - Irritant
  R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
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 37/39 - Wear suitable gloves and eye/face protection.
Human Experience: 10 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
  oral-rat LD50  2910 mg/kg
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

oral-mouse LD50  3900 mg/kg
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

oral-guinea pig LD50  2780 mg/kg
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

Dermal Toxicity:
  skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 12, Pg. 935, 1974.

Inhalation Toxicity:
  Not determined
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Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for methyl anthranilate usage levels up to:
  10.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 686.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 3764.00 (μg/capita/day)
Threshold of Concern:1800 (μg/person/day)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3. Update in publication number(s): 18
Click here to view publication 3
 average usual ppmaverage maximum ppm
baked goods: 38.0000038.00000
beverages(nonalcoholic): 40.0000040.00000
beverages(alcoholic): 0.200002.00000
breakfast cereal: --
cheese: --
chewing gum: 200.000001583.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 40.0000040.00000
fruit ices: 40.0000040.00000
gelatins / puddings: 20.0000020.00000
granulated sugar: --
gravies: --
hard candy: 80.00000161.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: 6.000006.00000
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 80.0000080.00000
soups: --
sugar substitutes: --
sweet sauces: --
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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):
Flavouring Group Evaluation 84, (FGE.84)[1] - Consideration of Anthranilate derivatives evaluated by JECFA (65th meeting) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf
Scientific Opinion on the safety and efficacy of anthranilate derivatives (chemical group 27) when used as flavourings for all animal species
View page or View pdf
EPI System: View Calculate predicted properties
NLM Hazardous Substances Data Bank: Search
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
National Toxicology Program: Search
EPA Substance Registry Services (TSCA): 134-20-3
EPA ACToR: Toxicology Data
National Institute of Allergy and Infectious Diseases: Data
WGK Germany:1
 methyl 2-aminobenzoate
DTP/NCI: 3109
Chemidplus: 0000134203
EPA/NOAA CAMEO:hazardous materials
RTECS: CB3325000 for cas# 134-20-3
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 methyl 2-aminobenzoate
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 134-20-3
Pubchem (cid): 8635
Pubchem (sid): 134974914
Flavornet: 134-20-3
Pherobase: View
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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
FDA Everything Added to Food in the United States (EAFUS): View
HMDB (The Human Metabolome Database): HMDB29703
Export Tariff Code: 2922.49.1000
Haz-Map: View
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
•grades: technical; fcc. •usepaopp pesticide code 128725; trade names: bird shield repellant concentrate (26.4%), rejex-it ag-145 (14.5%), rejex-it ag-36 (14.5%), rejex-it ma (98.5%), rejex-it tp-40 (40%).
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Potential Blenders and core components note
 acetaldehyde ethyl phenethyl acetalFL/FR
 acetyl tetralinFR
 allyl amyl glycolateFR
 allyl anthranilateFL/FR
 amyl anthranilateFL/FR
isoamyl benzoateFL/FR
alpha-amyl cinnamaldehydeFL/FR
isoamyl salicylateFL/FR
 amyris wood oilFL/FR
para-anisyl acetateFL/FR
para-anisyl alcoholFL/FR
 apple crotonateFR
 atractylis absoluteFR
 beeswax absoluteFL/FR
 benzyl anthranilateFL/FR
 benzyl cinnamateFL/FR
 benzyl isoeugenolFL/FR
 benzyl salicylateFL/FR
 bergamot oilFL/FR
 bigarade oxideFR
blood orange oil italyFL/FR
 buchu mercaptanFL/FR
 butyl anthranilateFL/FR
isobutyl anthranilateFL/FR
isobutyl isobutyrateFL/FR
isobutyl methyl anthranilateFL/FR
 cassia bark oil chinaFL/FR
 cassis bud oilFL/FR
 cassis oxime 10%FR
 cassis pentanoneFL/FR
 champaca absoluteFR
 cinnamyl alcoholFL/FR
 cinnamyl anthranilate 
 cinnamyl propionateFL/FR
 citral / methyl anthranilate schiff's baseFR
 citronellyl anthranilateFL/FR
 clary sage oil franceFL/FR
 clean nitrileFR
 clover nitrileFR
white cognac oilFL/FR
 curacao peel oilFL/FR
 cyclamen aldehyde / methyl anthranilate schiff's baseFR
 cyclohexyl anthranilateFL/FR
 cyclohexyl ethyl alcoholFL/FR
 decanal / methyl anthranilate schiff's baseFR
 decanal dimethyl acetalFL/FR
 decyl anthranilateFR
 decyl formateFR
 dimethyl anthranilateFL/FR
 dimethyl benzyl carbinolFL/FR
 dimethyl benzyl carbinyl acetateFL/FR
 dimethyl benzyl carbinyl butyrateFL/FR
meta-dimethyl hydroquinoneFL/FR
2,4-dimethyl-3-cyclohexene-1-methanyl acetateFR
 dodecanal (aldehyde C-12 lauric)FL/FR
 ethyl (E,Z)-2,4-decadienoateFL/FR
 ethyl 3-hydroxyhexanoateFL/FR
 ethyl anthranilateFL/FR
 ethyl cinnamateFL/FR
 ethyl decanoateFL/FR
 ethyl ethyl anthranilateFL/FR
 ethyl phenyl acetateFL/FR
 ethyl propionateFL/FR
 ethyl vanillinFL/FR
 fig crotonateFR
 fir balsam absoluteFR
 furfuryl butyrateFL
 gardenia amideFR
 gardenia decaloneFR
 gardenia pentyl acetateFR
 geranyl anthranilateFR
 geranyl formateFL/FR
 geranyl methyl tiglate 
 geranyl phenyl acetateFL/FR
 grape butyrateFL/FR
 grapefruit acetalFR
 grapefruit indeneFR
 grapefruit menthaneFL/FR
 grapefruit mercaptanFL/FR
 grapefruit nitrileFR
 dimethyl octenoneFR
 grapefruit oil c.p. californiaFL/FR
 grapefruit oil CO2 extract (citrus paradisi macf. var. falvedo)FL/FR
 grapefruit oil terpenelessFL/FR
 grapefruit pentanolFR
 green acetateFR
 green carboxylateFR
 heptanal dimethyl acetalFL/FR
(Z)-3-hexen-1-yl anthranilateFL/FR
(E)-2-hexen-1-yl isovalerateFL/FR
alpha-hexyl cinnamaldehydeFL/FR
 hexyl isobutyrateFL/FR
 hyacinth etherFR
 hydroxycitronellal / methyl anthranilate schiff's baseFR
 labdanum ethanoneFR
 leerall / methyl anthranilate schiff's baseFR
 lilyall / methyl anthranilate schiff's baseFR
 lime oil distilled terpenelessFL/FR
 linalyl anthranilateFL/FR
 linalyl cinnamateFL/FR
 linalyl phenyl acetateFL/FR
 magnolia indeneFR
 maltyl isobutyrateFL/FR
 mandarin oil (citrus reticulata var. ponkan)FL/FR
 melon heptenalFL/FR
 methyl 2-(methyl thio) butyrateFL
para-methyl acetophenoneFL/FR
alpha-methyl cinnamaldehydeFL/FR
 methyl cinnamateFL/FR
 methyl formyl anthranilateFL/FR
 methyl thiomethyl butyrateFL
 muguet carboxaldehydeFR
 myrmac aldehydeFR
beta-naphthyl anthranilateFL/FR
beta-naphthyl ethyl etherFL/FR
beta-naphthyl methyl etherFL/FR
alpha-naphthyl methyl ketoneFL/FR
beta-naphthyl methyl ketoneFL/FR
2-naphthyl phenyl ketone 
 nerol oxideFL/FR
 neroli oil bigardeFL/FR
 neroli oil CO2 extractFL/FR
 nerolidyl acetateFL/FR
 nerolin fragarolFL/FR
 neryl acetateFL/FR
 nonanal / methyl anthranilate schiff's baseFR
 nonanal dimethyl acetalFL/FR
 ocean propanalFL/FR
 ocean propanal / methyl anthranilate schiff's baseFR
 octanal / methyl anthranilate schiff's baseFR
3-octyl acetateFL/FR
sweet orange peel oil c.p. brazilFL/FR
bitter orangeflower absolute moroccoFL/FR
 orris rhizome resinoid (iris pallida)FL/FR
 passiflora acetateFL/FR
 peony acetonitrileFR
 petitgrain bigarade oilFL/FR
 petitgrain mandarin oilFL/FR
 petitgrain mandarin oil terpenelessFL/FR
 petitgrain oil paraguayFL/FR
 phenethyl acetateFL/FR
 phenethyl anthranilateFL/FR
 phenethyl phenyl acetateFL/FR
 phenyl acetaldehydeFL/FR
3-phenyl propionaldehydeFL/FR
(E)-2-phenyl-1(2)-propene-1-yl acetateFR
isopropenyl acetateFL/FR
 propyl anthranilateFL/FR
isopropyl anthranilateFL/FR
 propyl heptanoateFL/FR
 propyl isobutyrateFL/FR
 strawberry glycidate 1 (aldehyde C-16 (so-called))FL/FR
 surfleurs d'oranger oilFL/FR
alpha-terpinyl anthranilateFL/FR
alpha-terpinyl methyl etherFL/FR
 tonka ketoneFR
gamma-undecalactone (aldehyde C-14 (so-called))FL/FR
 wallflower absoluteFR
 ylang ylang flower oilFL/FR
 ylang ylang flower oil CO2 extractFL/FR
 ylang ylang flower oil IFL/FR
 ylang ylang flower oil IIFL/FR
 ylang ylang flower oil IIIFL/FR
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Potential Uses:
 acacia cassie farnesianaFR
 bubble gumFR
 champaca champakFR
 elder flowerFR
 forest pine forestFR
 genet genista broomFR
 grape concordFR
 melon watermelon muskmelon cantaloupe 
 orange blossomFR
 passion fruitFR
 petitgrain mandarinFL/FR
 quelques fleurs 
 sweet peaFR
 woodruff asperulaFR
 ylang ylangFR
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Natural Occurrence in: note
GRIN Trop Picture
 calvatia gigantea
GRIN Trop Picture
 champaca absolute @ 4.50%
Data  GC  GRIN Trop Picture
 champaca concrete @ 9.00%
Data  GC  GRIN Trop Picture
GRIN Trop Picture
GRIN Trop Picture
 genet absolute @ 0.40%
Data  GC  GRIN Trop Picture
 grape concord grape
GRIN Trop Picture
GRIN Trop Picture
 jasmin absolute concrete india @ 0.39-0.82%
Data  GC  GRIN Trop Picture
 jasmin absolute concrete italy @ 2.86%
Data  GC  GRIN Trop Picture
 jasmin sambac absolute egypt @ 4.90%
Data  GC  GRIN Trop Picture
 narcissus absolute @ 0.19%
Data  GC  GRIN Trop Picture
 narcissus absolute @ 0.43%
Data  GC  GRIN Trop Picture
 neroli bigarde oil france @ trace%
Data  GC  GRIN Trop Picture
 neroli oil CO2 extract @ 0.98%
Data  GC  GRIN Trop Picture
 orange peel oil sweet c.p. egypt @ 0.24%
Data  GC  GRIN Trop Picture
 orangeflower absolute morocco @ 1.0-4.3%
Data  GC  GRIN Trop Picture
 orangeflower water absolute @ 2.0-11.4%
Data  GC  GRIN Trop Picture
 rue oil
GRIN Trop Picture
GRIN Trop Picture
 tea green tea with jasmin
 wine white & red wine
 ylang ylang
GRIN Trop Picture
 ylang ylang oil @ 0.08%
Data  GC  GRIN Trop Picture
 ylang ylang oil CO2 extract @ 0.02%
Data  GC  GRIN Trop Picture
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o-amino methyl benzoate
2-amino-benzoic acid methyl ester
2-aminobenzoic acid methyl ester
o-aminobenzoic acid methyl ester
ortho-aminobenzoic acid methyl ester
o-aminomethyl benzoate
ortho-aminomethyl benzoate
 anthranilic acid methyl ester
 anthranilic acid methylester
 benzoic acid, 2-amino-, methyl ester
2-(methoxycarbonyl) aniline
 methyl 2-aminobenzoate
 methyl aminobenzoate
 methyl anthranilate (natural)
 methyl anthranilate extra
 methyl anthranilate extra BHT free
 methyl anthranilate extra FCC
 methyl anthranilate FCC
 methyl anthranilate natural
 methyl anthranilate natural EEC
 methyl anthranilate purified FCC
 methyl anthranilate, natural
 methyl o-aminobenzoate
 methyl ortho-aminobenzoate
 nevoli oil
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Info: anthranilate derivatives
PubMed: Heat and noxious chemical sensor, chicken TRPA1, as a target of bird repellents and identification of its structural determinants by multispecies functional comparison.
PubMed: Methyl anthranilate and γ-decalactone inhibit strawberry pathogen growth and Achene Germination.
PubMed: Comparative analysis of flower volatiles from nine citrus at three blooming stages.
PubMed: Electrochemical preparation of polyaniline-polypyrrole solid-phase microextraction coating and its application in the GC determination of several esters.
PubMed: Electrodeposition of poly(3,4-ethylenedioxythiophene) on a stainless steel wire for solid phase microextraction and GC determination of some esters with high boiling points.
PubMed: Piracetam, an AMPAkine drug, facilitates memory consolidation in the day-old chick.
PubMed: Methyl 2-(thio-phene-2-carboxamido)-benzoate.
PubMed: Assessing the effects of three potential chemical repellents to prevent bird damage to corn seeds and seedlings.
PubMed: Induced release of a plant-defense volatile 'deceptively' attracts insect vectors to plants infected with a bacterial pathogen.
PubMed: Liquid CO2 extraction of Jasminum grandiflorum and comparison with conventional processes.
PubMed: Memantine facilitates memory consolidation and reconsolidation in the day-old chick.
PubMed: Assessment of the validity of maturity metrics for predicting the volatile composition of Concord grape juice.
PubMed: [Study on constituents of essential oil from Lonicera fulvotomentosa in different collected periods].
PubMed: Evaluation of volatiles from two subtropical strawberry cultivars using GC-olfactometry, GC-MS odor activity values, and sensory analysis.
PubMed: A novel attractant for Anastrepha ludens (Diptera: Tephritidae) from a Concord grape product.
PubMed: Comparison of odor-active compounds in grapes and wines from vitis vinifera and non-foxy American grape species.
PubMed: Comparison of silica gel modified with three different functional groups with C-18 and styrene-divinylbenzene adsorbents for the analysis of selected volatile flavor compounds.
PubMed: A four-enzyme pathway for 3,5-dihydroxy-4-methylanthranilic acid formation and incorporation into the antitumor antibiotic sibiromycin.
PubMed: Antiandrogenic activity of anthranilic acid ester derivatives as novel lead structures to inhibit prostate cancer cell proliferation.
PubMed: Reconciling sensory cues and varied consequences of avian repellents.
PubMed: A solid-phase microextraction gas chromatography/ion trap tandem mass spectrometry method for simultaneous determination of 'foxy smelling compounds' and 3-alkyl-2-methoxypyrazines in grape juice.
PubMed: Herbivore-induced SABATH methyltransferases of maize that methylate anthranilic acid using s-adenosyl-L-methionine.
PubMed: Chemical composition and antibacterial, antifungal and antioxidant activities of the flower oil of Retama raetam (Forssk.) Webb from Tunisia.
PubMed: Different isolation methods for determination of composition of volatiles from Nigella damascena L. seeds.
PubMed: Enzymatic, expression and structural divergences among carboxyl O-methyltransferases after gene duplication and speciation in Nicotiana.
PubMed: An investigation of the inclusion complex of cyclomaltoheptaose (beta-cyclodextrin) with N-methylanthranilic acid in the solid state.
PubMed: Localized auxin biosynthesis and postembryonic root development in Arabidopsis.
PubMed: A comparison of citrus blossom volatiles.
PubMed: Effects of prenatal exposure to a 50-Hz magnetic field on one-trial passive avoidance learning in 1-day-old chicks.
PubMed: Reducing honey bee defensive responses and social wasp colonization with methyl anthranilate.
PubMed: Synthesis of some novel pyrazolo[3,4-b]pyridine and pyrazolo[3,4-d]pyrimidine derivatives bearing 5,6-diphenyl-1,2,4-triazine moiety as potential antimicrobial agents.
PubMed: Room-temperature palladium-catalyzed C-H activation: ortho-carbonylation of aniline derivatives.
PubMed: 2-(Methoxy-carbon-yl)anilinium dihydrogen phosphate.
PubMed: The type 4 phosphodiesterase inhibitors rolipram and YM976 facilitate recall of the weak version of the passive avoidance task in the day-old chick.
PubMed: Learning ability of 1-d-old partridges (Alectoris rufa) from eggs laid by hens fed with different n-3 fatty acid concentrations.
PubMed: A comparison of protocols for passive and discriminative avoidance learning tasks in the domestic chick.
PubMed: Microwave-assisted efficient and convenient synthesis of 2,4(1H,3H)-quinazolinediones and 2-thioxoquinazolines.
PubMed: A phosphine-mediated through-space exchange coupling pathway for unpaired electrons in a heterobimetallic lanthanide-transition metal complex.
PubMed: Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones.
PubMed: Quantification of flavor-related compounds in the unburned contents of bidi and clove cigarettes.
PubMed: Astrocytic energy metabolism consolidates memory in young chicks.
PubMed: Passive avoidance training decreases synapse density in the hippocampus of the domestic chick.
PubMed: Production of natural methyl anthranilate by microbial N-demethylation of N-methyl methyl anthranilate by the topsoil-isolated bacterium Bacillus megaterium.
PubMed: The biosynthesis and regulation of biosynthesis of Concord grape fruit esters, including 'foxy' methylanthranilate.
PubMed: Antifungal activity of tuberose absolute and some of its constituents.
PubMed: Further field evaluation of synthetic herbivore-induced plant volatiles as attractants for beneficial insects.
PubMed: The effect of solvent interactions on alpha-, beta-, and gamma-cyclodextrin/flavor molecular inclusion complexes.
PubMed: Field capture of northern and western corn rootworm beetles relative to attractant structure and volatility.
PubMed: Effects of purinenucleotide analogues on microtubule assembly.
PubMed: Facilitation of a weak training experience in the 1-day-old chick using diphenylhydantoin: a pharmacological and biochemical study.
PubMed: Calcium responses of chicken trigeminal ganglion neurons to methyl anthranilate and capsaicin.
PubMed: Facilitation and disruption of memory for the passive avoidance task in the day-old chick using dopamine D1 receptor compounds.
PubMed: Conjugate additions of o-iodoanilines and methyl anthranilates to acetylenic sulfones. A new route to quinolones including first syntheses of two alkaloids from the medicinal herb Ruta chalepensis.
PubMed: Passive avoidance training enhances cell proliferation in 1-day-old chicks.
PubMed: Identification of potent odorants in Chinese jasmine green tea scented with flowers of Jasminum sambac.
PubMed: Assessment of strawberry aroma through SPME/GC and ANN methods. Classification and discrimination of varieties.
PubMed: Thiourea derivatives and their nickel(II) and platinum(II) complexes: antifungal activity.
PubMed: Interference with Pseudomonas quinolone signal synthesis inhibits virulence factor expression by Pseudomonas aeruginosa.
PubMed: Palatability of bird repellents to Rattus norvegicus.
PubMed: Aversion of the feral pigeon and the house sparrow to pellets and sprouts treated with commercial formulations of methyl anthranilate.
PubMed: High-performance liquid chromatographic determination of methyl anthranilate, hydroxymethylfurfural and related compounds in honey.
PubMed: Dielectric properties of some components of fruit aroma in carbon tetrachloride solution at 298.15 K.
PubMed: Influence of packaging on the aroma stability of strawberry syrup during shelf life.
PubMed: Liquid chromatographic determination of methyl anthranilate in artificially flavored nonalcoholic beverages.
PubMed: Substrate-induced fit of the ATP binding site of cytidine monophosphate kinase from Escherichia coli: time-resolved fluorescence of 3'-anthraniloyl-2'-deoxy-ADP and molecular modeling.
PubMed: Determination of methyl anthranilate in food samples by coupling stopped-flow mixing technique and time-resolved luminescence detection.
PubMed: Comparison of methyl anthranilate and denatonium benzoate as aversants for learning in chicks.
PubMed: Passive avoidance training results in increased responsiveness of voltage- and ligand-gated calcium channels in chick brain synaptoneurosomes.
PubMed: Synthesis and evaluation of anthranilic acid-based transthyretin amyloid fibril inhibitors.
PubMed: Passive avoidance learning involves alpha2-noradrenergic receptors in a day old chick.
PubMed: Relative importance of odour and taste in the one-trial passive avoidance learning bead task.
PubMed: Response of domestic chicks to methyl anthranilate odour
PubMed: D-cycloserine causes transient enhancement of memory for a weak aversive stimulus in day-old chicks (Gallus domesticus).
PubMed: Passive avoidance learning in the day-old chick is modulated by GABAergic agents.
PubMed: Partial G protein activation by fluorescent guanine nucleotide analogs. Evidence for a triphosphate-bound but inactive state.
PubMed: Electrophysiological correlates of prior training: an in vitro study of an area of the avian brain which is essential for early learning.
PubMed: The involvement of dopamine in the striatum in passive avoidance training in the chick.
PubMed: Involvement of AMPA receptors in maintenance of memory for a passive avoidance task in day-old domestic chicks (Gallus domesticus).
PubMed: Increases in NMDA receptor binding are specifically related to memory formation for a passive avoidance task in the chick: a quantitative autoradiographic study.
PubMed: Volatile secretions of old world army antAenictus rotundatus and chemotaxonomic implications of army ant dufour gland chemistry.
PubMed: Dendritic spine density in the lobus parolfactorius of the domestic chick is increased 24 h after one-trial passive avoidance training.
PubMed: Corticosterone enhances long-term retention in one-day-old chicks trained in a weak passive avoidance learning paradigm.
PubMed: Transient benzodiazepine-GABAA receptor increase after a passive avoidance learning in synaptosomal membranes from chick forebrain.
PubMed: Tests and refinements of a general structure-activity model for avian repellents.
PubMed: Na+,K(+)-ATPase activity in young chicks after taste stimulation.
PubMed: Training-induced increases in neuronal activity recorded from the forebrain of the day-old chick are time dependent.
PubMed: Nonlethal rodent repellents: Differences in chemical structure and efficacy from nonlethal bird repellent.
PubMed: 7-Chlorokynurenate, an antagonist of the glycine binding site on the NMDA receptor, inhibits memory formation in day-old chicks (Gallus domesticus).
PubMed: Quantitative autoradiographic demonstration of changes in binding to delta opioid, but not mu or kappa receptors, in chick forebrain 30 minutes after passive avoidance training.
PubMed: New quinoline derivatives: synthesis and evaluation for antiinflammatory and analgesic properties--Note II.
PubMed: Spatial re-arrangement of the vesicle apparatus in forebrain synapses of chicks 30 min after passive avoidance training.
PubMed: Long-term increases in the numerical density of synapses in the chick lobus parolfactorius after passive avoidance training.
PubMed: Avoidance of bird repellents by mice (Mus musculus).
PubMed: Tryptophan analog resistance mutations in Chlamydomonas reinhardtii.
PubMed: Fluorescent N-methylanthranilyl (Mantyl) tag for peptides: its application in subpicomole determination of kinins.
PubMed: Role of electronic factors in binding and reduction of azo dyes by hepatic microsomes.
PubMed: Quantitative Autoradiographic Demonstration of Changes in Binding to NMDA-sensitive [3H]Glutamate and [3H]MK801, but not [3H]AMPA Receptors in Chick Forebrain 30 min After Passive Avoidance Training.
PubMed: Forebrain noradrenaline concentration following weakly reinforced training.
PubMed: Possible noradrenergic involvement in training stimulus intensity.
PubMed: Cerebral Glycoprotein Synthesis and Long-term Memory Formation in the Chick (Gallus domesticus) Following Passive Avoidance Training Depends on the Nature of the Aversive Stimulus.
PubMed: Memory consolidation of weak training experiences by hormonal treatments.
PubMed: New quinoline derivatives: synthesis and evaluation for antiinflammatory and analgesic properties--Note I.
PubMed: Sex differences in response to the odor of alpha androstenone.
PubMed: Chemistry of mandibular and Dufour's gland secretions of ants in genusMyrmecocystus.
PubMed: Effect of retraining trials on memory consolidation in weakly reinforced learning.
PubMed: Memory formation processes in weakly reinforced learning.
PubMed: Alterations in synaptic structure in the paleostriatal complex of the domestic chick, Gallus domesticus, following passive avoidance training.
PubMed: Cyclization under mild conditions of anthraniloyl- and N-methyl-anthraniloyl dipeptides.
PubMed: Lasting changes in spontaneous multi-unit activity in the chick brain following passive avoidance training.
PubMed: CGS 9343B, a novel, potent, and selective inhibitor of calmodulin activity.
PubMed: Analysis of anthranilic acid by liquid chromatography.
PubMed: Passive avoidance training increases fucose incorporation into glycoproteins in chick forebrain slices in vitro.
PubMed: Prostaglandin anthrylmethyl ester: a membrane-permeant fluorescent analogue of prostaglandin with enhanced cell growth inhibitory activity.
PubMed: Human (Homo sapiens) responses to the pig (Sus scrofa) sex pheromone 5 alpha-androst-16-en-3-one.
PubMed: Sensitive fluorographic detection of 3H and 14C on chromatograms using methyl anthranilate as a scintillant.
PubMed: Characterization of impurities in commercial lots of sodium saccharin produced by the Sherwin-Williams process. I. Chemistry.
PubMed: Studies on bacterial chemotaxis. III. Effect of methyl esters on the chemotactic response of Escherichia coli.
PubMed: Kidney and liver tumors in rats from 4,4'-methylene bis (2-carbomethoxyaniline).
PubMed: The hydrolysis of flavouring esters by artificial gastrointestinal juices and rat tissue preparations.
PubMed: A fluorescence detector for high-pressure liquid chromatography.
PubMed: [Reaction of furfural with methyl anthranilate and methyl 2-aminonicotinate (author's transl)].
PubMed: Media dependence of commitment in Bacillus subtilis.
PubMed: Initiation of spore germination in Bacillus subtilis: relationship to inhibition of L-alanine metabolism.
PubMed: Caste-specific compounds in male carpenter ants.
PubMed: Acute and short-term toxicity of methyl-N-methyl anthranilate in rats.
PubMed: Methyl anthranilate, an inhibitor for thegermination of spores of aerobic bacilli.
PubMed: [Research on methyl anthranilate in Spanish honey from orange flower by thin-layer chromatography].
PubMed: Assessment of the validity of maturity metrics for predicting the volatile composition of Concord grape juice.
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Soluble in:
 dipropylene glycol
 fixed oils
 propylene glycol
 water, 2850 mg/L @ 25 °C (exp)
Insoluble in:
 paraffin oil
 alcoholic lotion
 deo stick
 detergent perborate
 fabric softener
 liquid detergent
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