methyl anthranilate
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Notes :
grape enhancer - methyl anthranilate and phenethyl alcohol.
 
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IUPAC Name - methyl 2-aminobenzoate
InChI - InChI=1/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
InChIKey - VAMXMNNIEUEQDV-UHFFFAOYAV
SMILES - COC(=O)C1=CC=CC=C1N
CAS Number : 134-20-3
(EINECS) Number :205-132-4
Beilstein Number :0606965
FEMA Number :2682
COE Number :250
Molar Refractivity :42.26 ± 0.3 cm3 (est)
Parachor :337.9 ± 4.0 cm3 (est)
Index of Refraction :1.565 ± 0.02 (est)
Surface Tension :46.2 ± 3.0 dyne/cm (est)
Density :1.166 ± 0.06 g/cm3 (est)
Polarizability :16.75 ± 0.5 10-24cm3 (est)
XlogP : 1.60 (est)
Molecular Weight : 151.1625600 (IUPAC) (PT) (112)
Formula :C8 H9 N O2
Pherobase Floral:view
NMR Predictor :Predict
 
 
Category :flavor and fragrance agents

EU / EUROPA / FDA / JECFA Information :
JECFA Food Flavoring : 1534
Fl@vouring Number : 09.715
FDA Mainterm : METHYL ANTHRANILATE.
FDA Regulation. :FDA PART 182 -- SUBSTANCES GENERALLY RECOGNIZED AS SAFE
Subpart A--General Provisions
Sec. 182.60 Synthetic flavoring substances and adjuvants.

Suppliers :
Advanced Biotech :methyl anthranilate
98% min. natural
Odor:  Fruity, Grape
Bedoukian Research :METHYL ANTHRANILATE
≥98.0%, FCC, Kosher
Odor:  Characteristic concord grape, orange blossom aroma
A versatile material useful for its resemblance to orange flower.
Flavor:  sweet fruity
Used in a wide variety of flavors including grape, plum, blueberry and cherry.
Bell :Methyl Anthranilate
Berje :Methyl Anthranilate
Citrus and Allied Essences :Methyl Anthranilate Extra
FCC
Citrus and Allied Essences :Methyl Anthranilate
(natural)
Elan :methyl anthranilate
(natural), Kosher
Fleurchem :methyl anthranilate
natural
Fleurchem :methyl anthranilate
Givaudan :Methyl Anthranilate Extra
Odor:  Floral, Neroli, Warm, Sweet
Extensively used in many types of floral blends such as neroli and orange blossom, as well as in exotic compositions, gardenia, tuberose and jasmine, Methyl Anthranilate imparts warmth, volume and sweetness and is used in all types of perfumery.
IFF :Methyl Anthranilate
Odor:  Fruity, Grape, Floral
Fruity, floral, orange blossom, grape odor.
John D. Walsh :Methyl Anthranilate
Moellhausen :methyl anthranilate
99% min. nature identical kosher
Mooreganics :Methyl Anthranilate
Natural (Organic Compliant)
Odor:  MUSTY-FRUITY, FRY-FLORAL, CONCORD GRAPE, ORANGE BLOSSOM
Penta :methyl anthranilate
Penta :methyl anthranilate
natural
Polarome :METHYL ANTHRANILATE
FCC
SAFC Global® :Methyl anthranilate
≥98%, FCC, Kosher, FG
Odor:  chocolate; grape; grapefruit; jasmine; lemon; lime; musty; fruity; herbaceous; citrus; floral; strawberry; sweet; coffee; medicinal
SAFC Global® :Methyl anthranilate
≥99%, natural, Kosher, FG
Odor:  chocolate; grape; grapefruit; jasmine; lemon; lime; musty; fruity; herbaceous; citrus; floral; strawberry; sweet; coffee; medicinal
Vigon :Methyl Anthranilate Extra
FCC
Vigon :Methyl Anthranilate
Natural
Odor:  Floral, Neroli, Warm, Sweet

Organoleptics :
Odor Type :fruity
Odor Strength :medium
Odor Description:
at 100.00 %.  
fruity grape orangeflower neroli
Luebke, William tgsc, (1982)
Odor sample from :Berje Inc.
Odor Description:
Fruity, concord grape, musty with a floral powdery nuance
Mosciano, Gerard P&F 18, No. 2, 38, (1993)
Taste Description:
at 25.00 ppm.  
Sweet, fruity, concord grape, with a musty and berry nuance
Mosciano, Gerard P&F 18, No. 2, 38, (1993)
Substantivity :88  Hour(s)

Properties :
Appearence :pale yellow to dark yellow clear liquid to solid
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
Refractive Index :1.57900 to 1.59200 @ 20.00 °C.
Melting Point : 23.00 to 24.00 °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 :0.01000 mm/Hg @ 25.00 °C.
Vapor Density :5.2 ( Air = 1 )
Flash Point : 220.00  °F.  TCC  ( 104.44 °C. )
logP (o/w) : 1.88
Shelf Life : 24.00 month(s) or longer if stored properly.
Storage :store in cool, dry place in tightly sealed containers, protected from heat and light.

Safety :
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 Toxicity(LD50) : 
  Oral-Rat    2910.00  mg/kg
FCTXAV  2,327,1964

Oral-Mouse    3900.00  mg/kg

Oral-Guineapig    2780.00  mg/kg

Dermal Toxicity(LD50) : 
  Skin-Rabbit  >5000.00  mg/kg
FCTXAV  12,935,1974

Inhalation Toxicity(LC50) : 
  Not determined
 

Safety in Use :
Category :flavor and fragrance agents
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)
 
Recommendation for methyl anthranilate fragrance usage levels up to :
  10.0000 % in the fragrance concentrate.
Recommendation for methyl anthranilate flavor usage levels up to :
  2200.0000 ppm in the flavor.

Safety References :
European Food Safety Athority(efsa) :Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
msds :msds
EPI System :view
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
Canada Domestic Sub. List :Yes
EPA Chem. Sub. Inventory : Yes
 
WGK Germany :1
 
 
 
 
methyl 2-aminobenzoate
BioActivity Analysis :69638
dtp/nci :3109
(EINECS) Number :205-132-4
Chemidplus :000134203
EPA/NOAA CAMEO :hazardous materials
EPA Substance Registry Services :134-20-3
RTECS :CB3325000 for cas# 134-20-3

References :
 
methyl 2-aminobenzoate
NIST Chemistry WebBook :3796554741
Pubchem :151791
Flavornet :134-20-3

Cosmetics :
Cosmetic Uses : masking agents

Other :
CosIng :cosmetic data
 C of A
FDA Everything Added to Food in the United States (EAFUS)View
Export Tariff Code :2922.49.1000
FMA :listed
RIFM :listed
VCF-Online: VCF Volatile Compounds in Food
Synonyms :
2-aminobenzoic acid methyl ester
ortho-aminobenzoic acid methyl ester
ortho-aminomethyl benzoate
 anthranilic acid methyl ester
2-carbomethoxyaniline
ortho-carbomethoxyaniline
2-(methoxycarbonyl) aniline
 methyl 2-aminobenzoate
 methyl aminobenzoate
 methyl ortho-aminobenzoate
 nevoli oil

Soluble in :
 alcohol
 dipropylene glycol
 fixed oils
 propylene glycol
 water, 2850 mg/L @ 25C (est)

Insoluble in :
 paraffin oil
 glycerin
 water

Stability :
 alcoholic lotion
 antiperspirant
 deo stick
 detergent perborate
 fabric softener
 liquid detergent
 shampoo
 soap

Potential Blenders :    note
 acetaldehyde ethyl phenethyl acetalFL/FR
6-acetoxydihydrotheaspiraneFL/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-anisaldehydeFL/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
 citronellolFL/FR
 citronellyl anthranilateFL/FR
 clary sage oil franceFL/FR
 clean nitrileFR
 clover nitrileFR
 cognac oil whiteFL/FR
 curacao peel oilFL/FR
 cyclamen aldehyde / methyl anthranilate schiff's baseFR
 cyclohexyl anthranilateFL/FR
 cyclohexyl ethyl alcoholFL/FR
gamma-decalactoneFL/FR
 decanal / methyl anthranilate schiff's baseFR
 decanal dimethyl acetalFL/FR
(Z)-4-decen-1-alFL/FR
 decyl anthranilateFR
 decyl formateFR
 dehydronootkatoneFL
 dihydronootkatoneFL
 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
(E,E)-2,4-dodecadien-1-alFL
 dodecanal (aldehyde C-12 lauric)FL/FR
 dodecanolFL/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
 farneseneFL/FR
 fig crotonateFR
 fir balsam absoluteFR
 furfuryl butyrateFL
 gardenia amideFR
 gardenia decaloneFR
 gardenia pentyl acetateFR
 geraniolFL/FR
 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
 grapefruit 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
3-hexanoneFL/FR
(Z)-3-hexen-1-yl anthranilateFL/FR
(E)-2-hexen-1-yl isovalerateFL/FR
alpha-hexyl cinnamaldehydeFL/FR
 hexyl isobutyrateFL/FR
 hyacinth etherFR
 hydroxycitronellalFL/FR
 hydroxycitronellal / methyl anthranilate schiff's baseFR
 labdanum ethanoneFR
 leerallFR
 leerall / methyl anthranilate schiff's baseFR
 lilyallFR
 lilyall / methyl anthranilate schiff's baseFR
 lime oil distilled terpenelessFL/FR
laevo-linaloolFL/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
4-mercapto-4-methyl-2-pentanolFL
 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 
 nerolFL/FR
 nerol oxideFL/FR
 neroli bigarde oil franceFL/FR
 neroli oil CO2 extractFL/FR
 nerolidolFL/FR
 nerolidyl acetateFL/FR
 nerolin fragarolFL/FR
 neryl acetateFL/FR
(E,Z)-2,6-nonadien-1-alFL
 nonanal / methyl anthranilate schiff's baseFR
 nonanal dimethyl acetalFL/FR
(Z)-6-nonen-1-alFL/FR
 nootkatoneFL/FR
 ocean propanalFL/FR
 ocean propanal / methyl anthranilate schiff's baseFR
 octanal / methyl anthranilate schiff's baseFR
3-octyl acetateFL/FR
 orange peel oil sweet c.p. brazilFL/FR
 orangeflower absolute moroccoFL/FR
 orris root resinoidFL/FR
 passiflora acetateFL/FR
 peony acetonitrileFR
 petitgrain bigarade oilFL/FR
 petitgrain mandarin oilFL/FR
 petitgrain mandarin oil terpenelessFL/FR
 petitgrain oilFL/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
 rhubarb furanFR
 santallFR
 strawberry glycidate 1 (aldehyde C-16)FL/FR
 surfleurs d'oranger oilFL/FR
alpha-terpineolFL/FR
alpha-terpinyl anthranilateFL/FR
alpha-terpinyl methyl etherFL/FR
para-tolyl aldehydeFL/FR
 tonka ketoneFR
 tridecanalFL/FR
(±)-2,4,8-trimethyl-7-nonen-2-olFL/FR
gamma-undecalactone (aldehyde C-14)FL/FR
 valenceneFL/FR
 vanillinFL/FR
 viridiflorolFL/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

Potential Uses :
 acacia cassie farnesianaFR
 almondFR
 bananaFR
 bergamotFR
 bluebell 
 blueberryFR
 bouquetFR
 bubble gumFR
 champaca champakFR
 cherryFR
 chloe 
 citrusFR
 cloveFR
 cologneFR
 currantFR
 elder flowerFR
 floralFR
 forest pine forestFR
 gardeniaFR
 genet genista broomFR
 grape concordFR
 greenhouseFR
 habubaFR
 jasminFR
 leatherFR
 lemonFR
 lilyFR
 melon watermelon muskmelon cantaloupe 
 mulberryFR
 neroliFR
 orangeFR
 orange blossomFR
 orientalFR
 passion fruitFR
 petitgrain mandarinFL/FR
 pineappleFR
 plumFR
 poison 
 quelques fleurs 
 quinceFR
 sweet peaFR
 tangerineFR
 tuberoseFR
 violetFR
 wallflowerFR
 woodruff asperulaFR
 ylang ylangFR

Natural Occurrence in :    note
 bergamot  
 champaca  
data pagechampaca absolute @ 4.50% S
data pagechampaca concrete @ 9.00% S
 cocoa S
 coffee  
 gardenia  
data pagegenet absolute @ 0.40% S
 grape concord grape  
 grapefruit S
 jasmin  
data pagejasmin absolute concrete india @ 0.39-0.82% S
data pagejasmin absolute concrete italy @ 2.86% S
data pagejasmin sambac absolute egypt @ 4.90% S
 lemon  
 lime  
 mandarin  
data pagenarcissus absolute @ 0.19% S
data pagenarcissus absolute @ 0.43% S
 neroli  
data pageneroli bigarde oil france @ trace% S
data pageneroli oil CO2 extract @ 0.98% S
 orange  
data pageorange peel oil sweet c.p. egypt @ 0.24% S
data pageorangeflower absolute morocco @ 1.0-4.3% S
data pageorangeflower water absolute @ 2.0-11.4% S
 rue oil S
 strawberry S
 tangerine  
PbMdtea green tea with jasmin  
 tuberose  
 wine white & red wine  
 ylang ylang S
data pageylang ylang oil @ 0.08% S
data pageylang ylang oil CO2 extract @ 0.02% S



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