dimethyl anthranilate
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IUPAC name :methyl 2-methylaminobenzoate
InChI :InChI=1/C9H11NO2/c1-10-8-6-4-3-5-7(8)9(11)12-2/h3-6,10H,1-2H3
InChIKey :GVOWHGSUZUUUDR-UHFFFAOYAS
SMILES :CNC1=CC=CC=C1C(=O)OC
cas number :85-91-6
(EINECS) number :201-642-6
beilstein number :0607217
fema number :2718
coe number :756
jecfa number :1545
fl. number :09.781
molar refractivity :47.63 ± 0.3 cm3
parachor :371.0 ± 4.0 cm3
index of refraction :1.562 ± 0.02
surface tension :40.8 ± 3.0 dyne/cm
density :1.125 ± 0.06 g/cm3
polarizability :18.88 ± 0.5 10-24cm3
XlogP : 2.00
molecular weight : 165.1891400 (IUPAC)
formula :C9 H11 N O2
BioActivity Analysis :74900
pherobase floral:view
NMR Predictor :Predict
 
 
export tariff code :2922.49.3800
fda reg :172.515

Suppliers :
Advanced Biotech :dimethyl anthranilate
98% min. natural
Bedoukian Research :DIMETHYL ANTHRANILATE
≥98.0%, FCC, Kosher
Odor:  Orange blossom and grape-like
A pleasant orange blossom character for fine fragrances.
Flavor:  fruity grape
Used in concord grape, green apple, cherry and dried fruit (raisin, prune) flavors for pitty woody notes.
Cargill :DIMETHYL ANTHRANILATE (EU NAT)
natural, Kosher
Odor:  Fruity, Musty, Sweet, Grape
Fleurchem :dimethyl anthranilate
natural
Fleurchem :dimethyl anthranilate
Givaudan :Dimethyl Anthranilate
Odor:  Orange flower, Mandarine, Neroli
Dimethyl Anthranilate is similar in use to Methyl Anthranilate, but it will not form Schiff bases with the aldehydes and has little or no tendency to discolour.
Mane :dimethyl anthranilate
Moellhausen :dimethyl anthranilate
60% min. nature identical kosher
Odor:  sweet, citrus, mandarin -tangerine
Flavor:  citrus, orange, mandarin.
Moellhausen :dimethyl anthranilate
99% min. nature identical kosher
Odor:  sweet, citrus, mandarin -tangerine
Flavor:  citrus, orange, mandarin.
Mooreganics :Dimethyl Anthranilate
Natural (Organic Compliant)
Odor:  ORANGE PEEL, MUSTY
Payand Betrand :Methyl methylanthranilate
Egypt, Natural Isolated Constituent
Penta :dimethyl anthranilate
Penta :dimethyl anthranilate
natural
Polarome :DIMETHYL ANTHRANILATE
FCC
Robertet :Dimethylanthranilate (methyl n-methylanthranilate)
naturel
SAFC Global® :Diethyl anthranilate
≥97%, Kosher
Odor:  blossom; grape; orange
SAFC Global® :Dimethyl anthranilate
≥98%, natural, FCC, Kosher
Odor:  blossom; grape; orange
Vigon :Dimethyl Anthranilate
Odor:  Orange flower, Mandarine, Neroli

organoleptics :
odor type :floral
odor strength :medium
odor description:
at 100.00 %.  
fruity musty sweet neroli powdery phenolic wine
Luebke, William tgsc, (1987)
odor sample from :Harrmann & Reimer Corporation
odor description:
Sweet, fruity anthranilate-like with a clean fresh floral nuance
Mosciano, Gerard P&F 16, No. 1, 31, (1991)
taste description:
at 10.00 ppm.  
Fruity grape skin, anthranilate-like with a woody and floral nuance
Mosciano, Gerard P&F 16, No. 1, 31, (1991)
substantivity :48  Hour(s)

properties :
appearence :pale yellow to amber clear liquid to solid
assay : 98.00 to 100.00 %   sum of isomers
Food Chemicals Codex Listed :Yes
specific gravity :1.12500 to 1.13000 @ 25.00 °C.
pounds per gallon - calc. : 9.361 to 9.403
refractive index :1.57900 to 1.58100 @ 20.00 °C.
melting point : 17.00 to 19.00 °C. @ 760.00 mm Hg
boiling point : 255.00 to 256.00 °C. @ 760.00 mm Hg
boiling point : 130.00 to 131.00 °C. @ 13.00 mm Hg
congealing point :12.00 °C.
acid value : 1.00  max.  KOH/g
vapor pressure :0.01000 mm/Hg @ 20.00 °C.
vapor density :>1 ( Air = 1 )
flash point :> 230.00  °F.  TCC  ( > 110.00 °C. )
logP (o/w) : 2.81
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.
R 42 - May cause sensitisation by inhalation.
R 42/43 - May cause sensitization by inhalation and skin contact.
R 43 - May cause sensitisation by skin contact.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Human experience : 10 % solution: no irritation or sensitization.
Oral Toxicity(LD50) : 
  Oral-Rat    3380.00  mg/kg

intravenous-Mouse    180.00  mg/kg

Dermal Toxicity(LD50) : 
  Skin-Rabbit  5000.00  mg/kg

Inhalation Toxicity(LC50) : 
  Not determined
 

safety in use :
Category :flavor and fragrance agents
Maximised Survey-derived Daily Intakes (MSDI-EU) :51.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA) :120.00 (μg/capita/day)
Threshold of concern :1800 (μg/person/day)
 
IFRA critical Effect :Phototoxicity
IFRA fragrance material specification :
 For applications on areas of the skin exposed to sunlight, excluding bath preparations, soaps and other wash-off products, limit to 10% in the finished cosmetic product. Based on the phototoxic potential and on the observed no-effect level of approximately 2 mg/cm2 of the hairless mouse (Food and Chemical Toxicology 17, 273 (1979)).
limits in the finished product for - "leave on the skin contact" :
  0.1000 % Restriction.
recommendation for dimethyl anthranilate fragrance usage levels up to :
  8.0000 % in the fragrance concentrate.
recommendation for dimethyl anthranilate flavor usage levels up to :
  30.0000 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
IFRA :IFRA - ( Found under : Methyl N-methylanthranilate )
Chemical Carcinogenesis Research Information System :Search
Env. Mutagen Info. Center :Search
NLM Developmental and Reproductive Toxicity :Search
Canada Domestic Sub. List :Yes
EPA Chem. Sub. Inventory : Yes
SCCNFP :opinion
 
WGK Germany :1
 
 
 
 
methyl 2-methylaminobenzoate
(EINECS) number :201-642-6
RTECS :CB3500000 for cas# 85-91-6
chemidplus :000085916
EPA Substance Registry Services :85-91-6
dtp/nci :9406

references :
 
methyl 2-methylaminobenzoate
fl. number :09.781
jecfa number :1545
NIST Chemistry WebBook :2075734128
pubchem :149826

Cosmetics :
Cosmetic uses : perfuming agents

other :
CosIng :cosmetic data
VCF-Online: VCF Volatile Compounds in Food
 C of A
RIFM :listed
FMA :listed
FDA Everything Added to Food in the United States (EAFUS)View
synonyms :
 dimethyl anthranilate
 methyl 2-(methyl amino) benzoate
 methyl 2-methylaminobenzoate
2-(methyl amino) benzoic acid methyl ester
2-methyl aminomethyl benzoate
 methyl anthranilic acid methyl ester
N-methyl anthranilic acid methyl ester
 methyl methanthranilate
 methyl methyl aminobenzoate
 methyl methyl anthranilate
 methyl N-methyl anthranilate
 methyl N-methyl-2-aminobenzoate
 methyl N-methyl-ortho-anthranilate
 methyl ortho-(methyl amino) benzoate
 methyl ortho-methyl aminobenzoate

soluble in :
 alcohol
 dipropylene glycol
 fixed oils
 water, 475 mg/L @ 20C

insoluble in :
 water
 glycerin

stability :
 bath foam
 cream
 hair spray
 lotion
 powder
 shampoo
 soap

potential blenders :    note
 acetaldehyde ethyl phenethyl acetalFL/FR
6-acetoxydihydrotheaspiraneFL/FR
isoamyl benzoateFL/FR
alpha-amyl cinnamaldehydeFL/FR
isoamyl salicylateFL/FR
para-anisaldehydeFL/FR
para-anisyl acetateFL/FR
para-anisyl alcoholFL/FR
 benzyl acetateFL/FR
 benzyl alcoholFL/FR
 benzyl cinnamateFL/FR
 benzyl propionateFL/FR
 bergamot oilFL/FR
 bigarade oxideFR
 blood orange oilFL/FR
 bois de rose oilFL/FR
 butyl anthranilateFL/FR
isobutyl anthranilateFL/FR
isobutyl methyl anthranilateFL/FR
 cardamom seed oilFL/FR
 cassis bud oilFL/FR
 cinnamyl alcoholFL/FR
 cinnamyl anthranilateFR
 citronellolFL/FR
 citronellyl anthranilateFL/FR
 citrus carbaldehydeFR
 clover nitrileFR
 coriander seed oilFL/FR
 curacao peel oilFL/FR
 currant bud absolute blackFL/FR
 cyclamen aldehyde / methyl anthranilate schiff's baseFR
 cyclohexyl anthranilateFL/FR
 cyclohexyl ethyl alcoholFL/FR
alpha-damasconeFL/FR
beta-damasconeFL/FR
 davana oilFL/FR
 decanal dimethyl acetalFL/FR
 decanolFL/FR
 decyl anthranilateFR
 dihydronootkatoneFL
1,3-dimethoxybenzeneFL/FR
 dimethyl benzyl carbinyl butyrateFL/FR
 dimethyl benzyl carbinyl isobutyrateFR
(E,Z)-2,6-dodecadien-1-alFL/FR
 dodecanolFL/FR
(E)-2-dodecen-1-alFL/FR
 ethyl cinnamateFL/FR
 ethyl ethyl anthranilateFL/FR
 ethyl methyl anthranilateFL/FR
 ethyl propionateFL/FR
 farneseneFL/FR
 floral pyranolFR
 furfuryl butyrateFL
 geraniolFL/FR
 geranyl anthranilateFR
 geranyl formateFL/FR
 grape butyrateFL/FR
 heliotropinFL/FR
 heliotropyl acetoneFL/FR
 herbal careneFR
(Z)-3-hexen-1-yl anthranilateFL/FR
(Z)-3-hexen-1-yl benzoateFL/FR
(Z)-3-hexen-1-yl salicylateFL/FR
 hexyl 2-methyl butyrateFL/FR
alpha-hexyl cinnamaldehydeFL/FR
 hyacinth etherFR
 ionones 
 leerallFR
 lime oil distilled terpenelessFL/FR
 linaloolFL/FR
laevo-linaloolFL/FR
 linalool oxideFL/FR
 linalyl acetateFL/FR
 linalyl cinnamateFL/FR
 linalyl phenyl acetateFL/FR
 mandarin oilFL/FR
 mandarin oil italyFL/FR
 mandarine undecenalFL/FR
 methyl anthranilateFL/FR
 methyl cinnamateFL/FR
 methyl dihydrojasmonateFL/FR
 methyl formyl anthranilateFL/FR
 methyl ionones 
alpha-methylene citronellalFR
 mikan peel oilCS
beta-naphthyl anthranilateFL/FR
beta-naphthyl ethyl etherFL/FR
beta-naphthyl methyl etherFL/FR
beta-naphthyl methyl ketoneFL/FR
 nerolFL/FR
 neroli oilFL/FR
 neroli oil CO2 extractFL/FR
 nerolidolFL/FR
 nerolidyl acetateFL/FR
 nonanolFL/FR
 nonyl anthranilate 
 ocean propanalFL/FR
 orange oilFL/FR
 orangeflower absoluteFL/FR
 orangeflower water absoluteFL/FR
 petitgrain cedrat oilFL/FR
 petitgrain combava oilCS
 petitgrain heptaneFR
 petitgrain mandarin oilFL/FR
 petitgrain mandarin oil terpenelessFL/FR
 petitgrain oilFL/FR
 phenethyl acetateFL/FR
 phenethyl alcoholFL/FR
 phenethyl phenyl acetateFL/FR
 phenethyl propionateFL/FR
 phenyl acetaldehydeFL/FR
3-phenyl propionaldehydeFL/FR
3-phenyl propyl alcoholFL/FR
(E)-2-phenyl-1(2)-propene-1-yl acetateFR
isopropyl anthranilateFL/FR
 rhodinolFL/FR
 rose butanoateFL/FR
alpha-sinensalFL/FR
 strawberry glycidate 1FL/FR
 tangerine acetateFR
 tangerine nitrileFR
 tangerine oilFL/FR
 tangerine oil terpenelessFL/FR
alpha-terpineolFL/FR
(E)-2-tridecen-1-alFL/FR
2-tridecen-1-alFL/FR
gamma-undecalactoneFL/FR
10-undecen-1-alFL/FR
 watermelon ketoneFR
 waxy nitrileFR
 ylang ylang oilFL/FR

potential uses :
 a suma
 acacia
 amber
 apple green apple
 apricot
 berry
 birch beer
 blackberry
 cabochard
 cherry
 cinq fleurs forvil
 citrus
 cranberry
 currant
 enhancer
 fern fougere
 floral
 fruit punch
 gooseberry
 grape
 heather
 honey miel
 huckleberry bilberry
 hyacinth jacinthe
 jasmin
 jonquil narcissus jonquilla
 linden blossom limeflower tilleul
 lux beauty shower soap
 mandarin
 mimosa wattle
 mulberry
 neroli
 orange blossom fleur d'oranger
 oriental
 peach
 petitgrain mandarin petitgrain
 petitgrain orange petitgrain
 petitgrain tangerine petitgrain
 plum
 raspberry
 rootbeer
 rue
 sarsaparilla
 strawberry
 tangerine
 tea
 tuberose tubereuse
 wintergreen
 wistaria wisteria glycine

natural occurrence in :    note
 broom absolute S
data pagechampaca concrete @ 0.05% S
 hyacinth S
 mandarin  
data pagemandarin oil avana @ 0.48% S
data pagemandarin oil italy @ 0.50% S
 petitgrain S
data pagepetitgrain lemon oil @ 0.25% S
 rue S
data pageyuzu leaf oil @ 45.36-58.50% S
PbMdzanthoxylum tingoassuiba S



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