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W268216

Sigma-Aldrich

Methyl anthranilate

natural (US), ≥99%, FG

Synonym(s):

Methyl 2-aminobenzoate, Methyl anthranilate

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About This Item

Linear Formula:
2-(H2N)C6H4CO2CH3
CAS Number:
134-20-3
Molecular Weight:
151.16
FEMA Number:
2682
Beilstein/REAXYS Number:
606965
EC Number:
205-132-4
Council of Europe no.:
250c
MDL number:
MFCD00007710
UNSPSC Code:
12164502
PubChem Substance ID:
24901248
Flavis number:
9.715

grade

FG
Halal
Kosher
natural (US)

reg. compliance

EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 117

vapor pressure

1 mmHg ( 20 °C)

assay

≥99%

autoignition temp.

986 °F

refractive index

n20/D 1.582 (lit.)

bp

256 °C (lit.)

mp

24 °C (lit.)

density

1.168 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

organoleptic

chocolate; coffee; grape; grapefruit; jasmine; lemon; lime; medicinal; musty; herbaceous; citrus; strawberry; sweet

SMILES string

COC(=O)c1ccccc1N

InChI

1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3

InChI key

VAMXMNNIEUEQDV-UHFFFAOYSA-N

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General description

Natural Occurrence: Cocoa, coffee, grape, grapefruit, jasmine, lemon, lime, mandarin, strawberry and tangerine.

Biochem/physiol Actions

Taste at 2-5 ppm

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

262.4 °F - closed cup

flash_point_c

128 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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N R Lien et al.
Carbohydrate research, 344(18), 2606-2608 (2009-11-03)
A 2:1 complex between cyclomaltoheptaose (beta-cyclodextrin) and N-methylanthranilic acid has been studied in the solid state. The inclusion complex belongs to the triclinic system (space group P1) with unit cell dimensions a=15.2773(15)A, b=15.4710(15)A, c=17.9627(18)A, alpha=99.632(5) degrees , beta=113.416(5) degrees
Mosciano, G.
Perfumer & Flavorist, 27, 58-58 (2002)
T H Burne et al.
Physiology & behavior, 62(6), 1299-1302 (1998-01-07)
The relative importance of taste and odour cues in a one-trial passive avoidance learning (PAL) task was examined. One-day-old chicks were presented with a small bead and different combinations of the taste and odour of methyl anthranilate (MeA). The chicks
Chris E Houlden et al.
Angewandte Chemie (International ed. in English), 48(10), 1830-1833 (2009-01-27)
Pd and CO--ureally got me! The title reaction proceeds efficiently at 18 degrees C under CO (1 atm) with 5 % [Pd(OTs)(2)(MeCN)(2)] as precatalyst. Depending on the solvents used, either anthranilates or cyclic imides can be obtained in high yields
Marcus Taupp et al.
Journal of agricultural and food chemistry, 53(24), 9586-9589 (2005-11-24)
Bacillus megaterium, isolated in a screening process from topsoil, was used for N-demethylation of natural N-methyl methyl anthranilate to produce natural methyl anthranilate. Maximal productivity of 70 mg/L/day was achieved under laboratory-scale conditions without further optimization. No byproducts were observed.
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