Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2. It has a strong and fruity grape smell, and one of its key uses is as a flavoring agent.
It is a colorless to pale yellow liquid with melting point 24 °C and boiling point 256 °C. It has a density of 1.168 g/cm3 at 20 °C.[1] It has a refractive index of 1.583 at 589 nm of wavelength and 20 °C.[2] It shows a light blue-violet fluorescence. It is very slightly soluble in water, and soluble in ethanol and propylene glycol. It is insoluble in paraffin oil. It is combustible, with flash point at 104 °C. Pure, it has a fruity grape smell; at 25 ppm it has a sweet, fruity, Concord grape-like smell with a musty and berry nuance.[3][4]
Usesedit
Methyl anthranilate acts as a bird repellent by irritating sensory receptors.[5] Dimethyl anthranilate (DMA) has a similar effect. It is also used for part of the flavor of grape Kool-Aid. It is used for flavoring of candy, soft drinks (e.g. grape soda), fruit (e.g. Grāpples), chewing gum, and nicotine products.[6]
Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery.[3][7] It is also used to produce Schiff bases with aldehydes, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol,[8] produced by combining methyl anthranilate and hydroxycitronellal.[9]
In organic synthesis, methyl anthranilate can be used as a source of the highly reactive aryne, benzyne. It is obtained by diazotization of the amine group using sodium nitrite which eliminates nitrogen and CO2 giving benzyne as an intermediate for Diels-Alder addition or other substitution at the ring.[10]
^Kováts, Kugler (1963). "Zur Kenntnis ätherischer Öle. 1. Mitteilung. Zur Kenntnis des Mandarinenschalen-Öls (Citrus reticulata BLANCO, bzw. Citrus nobilis var. deliciosa SWINGLE "Mandarin")". Helvetica Chimica Acta. 46 (5): 1480–1513. doi:10.1002/hlca.19630460506.
^Halama; Pytela (1996). "Steric Effects in Acid-Catalyzed Decomposition and Base-Catalyzed Cyclization of 1-(2-Alkoxycarbonylphenyl)-3-phenyltriazenes". Collection of Czechoslovak Chemical Communications. 61 (5): 751. doi:10.1135/cccc19960751.
^Ahmad, Shahzad, et al. "Effectiveness of methylanthranilate and anthraquinone as repellent against house crows (Corvus splendens) on wheat seeds and seedlings in captivity." Pakistan Journal of Zoology 48.5 (2016).
^Brown, Jessica E.; Luo, Wentai; Isabelle, Lorne M.; Pankow, James F. (2014). "Candy Flavorings in Tobacco". New England Journal of Medicine. 370 (23): 2250–2252. doi:10.1056/NEJMc1403015. PMID 24805984.
^Tadross, Pamela M.; Stoltz, Bryan (2012). "A Comprehensive History of Arynes in Natural Product Total Synthesis". Chem. Rev. 112 (6): 3550–3577. doi:10.1021/cr200478h. PMID 22443517. Retrieved 20 November 2022.
^Daniele Fraternale, Donata Ricci, Guido Flamini and Giovanna Giomaro. Volatiles Profile of Red Apple from Marche Region (Italy). Rec. Nat. Prod. (2011), 5:3; 202-207. pdf
January 01, 1970
methyl, anthranilate, confused, with, menthyl, anthranilate, also, known, methyl, aminobenzoate, carbomethoxyaniline, ester, anthranilic, acid, chemical, formula, c8h9no2, strong, fruity, grape, smell, uses, flavoring, agent, names, preferred, iupac, name, met. Not to be confused with Menthyl anthranilate Methyl anthranilate also known as MA methyl 2 aminobenzoate or carbomethoxyaniline is an ester of anthranilic acid Its chemical formula is C8H9NO2 It has a strong and fruity grape smell and one of its key uses is as a flavoring agent Methyl anthranilate Names Preferred IUPAC name Methyl 2 aminobenzoate Identifiers CAS Number 134 20 3 Y 3D model JSmol Interactive image ChEBI CHEBI 73244 N ChEMBL ChEMBL1493986 ChemSpider 13858096 N ECHA InfoCard 100 004 667 EC Number 205 132 4 KEGG C20634 N PubChem CID 8635 UNII 981I0C1E5W CompTox Dashboard EPA DTXSID6025567 InChI InChI 1S C8H9NO2 c1 11 8 10 6 4 2 3 5 7 6 9 h2 5H 9H2 1H3 NKey VAMXMNNIEUEQDV UHFFFAOYSA N NInChI 1 C8H9NO2 c1 11 8 10 6 4 2 3 5 7 6 9 h2 5H 9H2 1H3Key VAMXMNNIEUEQDV UHFFFAOYAV SMILES COC O c1c N cccc1 Properties Chemical formula C8H9NO2 Molar mass 151 165 Appearance colorless liquid Odor grape like Density 1 168 g cm3 Melting point 24 C 75 F 297 K Boiling point 256 C 493 F 529 K Hazards GHS labelling Pictograms Signal word Warning Hazard statements H319 Precautionary statements P264 P280 P305 P351 P338 P337 P313 Flash point 104 C 219 F 377 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Chemical properties 2 Uses 3 Occurrence 4 ReferencesChemical properties editIt is a colorless to pale yellow liquid with melting point 24 C and boiling point 256 C It has a density of 1 168 g cm3 at 20 C 1 It has a refractive index of 1 583 at 589 nm of wavelength and 20 C 2 It shows a light blue violet fluorescence It is very slightly soluble in water and soluble in ethanol and propylene glycol It is insoluble in paraffin oil It is combustible with flash point at 104 C Pure it has a fruity grape smell at 25 ppm it has a sweet fruity Concord grape like smell with a musty and berry nuance 3 4 Uses editMethyl anthranilate acts as a bird repellent by irritating sensory receptors 5 Dimethyl anthranilate DMA has a similar effect It is also used for part of the flavor of grape Kool Aid It is used for flavoring of candy soft drinks e g grape soda fruit e g Grapples chewing gum and nicotine products 6 Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma chemical is used extensively in modern perfumery 3 7 It is also used to produce Schiff bases with aldehydes many of which are also used in perfumery In a perfumery context the most common Schiff s Base is known as aurantiol 8 produced by combining methyl anthranilate and hydroxycitronellal 9 In organic synthesis methyl anthranilate can be used as a source of the highly reactive aryne benzyne It is obtained by diazotization of the amine group using sodium nitrite which eliminates nitrogen and CO2 giving benzyne as an intermediate for Diels Alder addition or other substitution at the ring 10 Occurrence editMethyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes and hybrids thereof and in bergamot black locust champak gardenia jasmine lemon mandarin orange neroli oranges rue oil strawberry tuberose wisteria galangal and ylang ylang It is also a primary component of the essential apple flavor along with ethyl acetate and ethyl butyrate 11 References edit Kovats Kugler 1963 Zur Kenntnis atherischer Ole 1 Mitteilung Zur Kenntnis des Mandarinenschalen Ols Citrus reticulata BLANCO bzw Citrus nobilis var deliciosa SWINGLE Mandarin Helvetica Chimica Acta 46 5 1480 1513 doi 10 1002 hlca 19630460506 Halama Pytela 1996 Steric Effects in Acid Catalyzed Decomposition and Base Catalyzed Cyclization of 1 2 Alkoxycarbonylphenyl 3 phenyltriazenes Collection of Czechoslovak Chemical Communications 61 5 751 doi 10 1135 cccc19960751 a b The Good Scents Company Methyl anthranilate The Japan Food Chemical Research Foundation Ahmad Shahzad et al Effectiveness of methylanthranilate and anthraquinone as repellent against house crows Corvus splendens on wheat seeds and seedlings in captivity Pakistan Journal of Zoology 48 5 2016 Brown Jessica E Luo Wentai Isabelle Lorne M Pankow James F 2014 Candy Flavorings in Tobacco New England Journal of Medicine 370 23 2250 2252 doi 10 1056 NEJMc1403015 PMID 24805984 An Introduction to Perfumery by Curtis amp Williams 2nd Edition 2009 ISBN 978 0 9608752 8 3 ISBN 978 1 870228 24 4 The Chemistry of Fragrances From Perfumer to Consumer ed Charles Sell ISBN 0 85404 824 3 ISBN 978 085404 824 3 Good Scents Company Page for Aurantiol Tadross Pamela M Stoltz Bryan 2012 A Comprehensive History of Arynes in Natural Product Total Synthesis Chem Rev 112 6 3550 3577 doi 10 1021 cr200478h PMID 22443517 Retrieved 20 November 2022 Daniele Fraternale Donata Ricci Guido Flamini and Giovanna Giomaro Volatiles Profile of Red Apple from Marche Region Italy Rec Nat Prod 2011 5 3 202 207 pdf Retrieved from https en wikipedia org w index php title Methyl anthranilate amp oldid 1216939499, 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