187:
40:
473:
31:
555:
630:
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/cm at 20 °C. It has a refractive index of 1.583 at 589 nm of wavelength and 20 °C. It shows a light blue-violet
481:
453:
824:
Kováts, Kugler (1963). "Zur
Kenntnis ätherischer Öle. 1. Mitteilung. Zur Kenntnis des Mandarinenschalen-Öls (Citrus reticulata BLANCO, bzw. Citrus nobilis var. deliciosa SWINGLE "Mandarin")".
523:
686:
Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery. It is also used to produce
902:
Ahmad, Shahzad, et al. "Effectiveness of methylanthranilate and anthraquinone as repellent against house crows (Corvus splendens) on wheat seeds and seedlings in captivity."
568:
694:, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol, produced by combining methyl anthranilate and
891:
344:
851:
Halama; Pytela (1996). "Steric
Effects in Acid-Catalyzed Decomposition and Base-Catalyzed Cyclization of 1-(2-Alkoxycarbonylphenyl)-3-phenyltriazenes".
969:
961:
993:
985:
309:
667:
by irritating sensory receptors. Dimethyl anthranilate (DMA) has a similar effect. It is also used for part of the flavor of grape
1062:
Daniele
Fraternale, Donata Ricci, Guido Flamini and Giovanna Giomaro. Volatiles Profile of Red Apple from Marche Region (Italy).
519:
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622:. It has a strong and fruity grape smell, and one of its key uses is as a flavoring agent.
266:
1005:
880:
796:
776:
764:
740:
730:
701:
In organic synthesis, methyl anthranilate can be used as a source of the highly reactive
80:
186:
124:
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772:
735:
546:
1079:
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710:
652:
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at 104 °C. Pure, it has a fruity grape smell; at 25 ppm it has a sweet, fruity,
438:
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30:
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916:
Brown, Jessica E.; Luo, Wentai; Isabelle, Lorne M.; Pankow, James F. (2014).
837:
501:
672:
1042:
943:
799:. It is also a primary component of the essential apple flavor, along with
980:
The
Chemistry of Fragrances: From Perfumer to Consumer, ed. Charles Sell,
956:
An
Introduction to Perfumery by Curtis & Williams 2nd Edition, 2009,
934:
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713:
of the amine group using sodium nitrite which eliminates nitrogen and CO
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1034:
1019:"A Comprehensive History of Arynes in Natural Product Total Synthesis"
768:
135:
545:
Except where otherwise noted, data are given for materials in their
221:
760:
702:
603:
115:
103:
93:
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212:
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318:
InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
328:
InChI=1/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
876:
874:
635:. It is very slightly soluble in water, and soluble in
563:
853:Collection of Czechoslovak Chemical Communications
245:
79:
8:
881:The Good Scents Company: Methyl anthranilate
729:Methyl anthranilate naturally occurs in the
721:addition or other substitution at the ring.
892:The Japan Food Chemical Research Foundation
655:-like smell with a musty and berry nuance.
1017:Tadross, Pamela M.; Stoltz, Bryan (2012).
185:
163:
22:
933:
265:
816:
683:), chewing gum, and nicotine products.
349:
314:
294:
717:giving benzyne as an intermediate for
539:104 °C (219 °F; 377 K)
443:256 °C (493 °F; 529 K)
176:
321:Key: VAMXMNNIEUEQDV-UHFFFAOYSA-N
143:
123:
7:
433:24 °C (75 °F; 297 K)
739:grapes and hybrids thereof, and in
331:Key: VAMXMNNIEUEQDV-UHFFFAOYAV
236:
220:
14:
553:
471:
38:
29:
922:New England Journal of Medicine
549:(at 25 °C , 100 kPa).
663:Methyl anthranilate acts as a
1:
1004:Good Scents Company Page for
918:"Candy Flavorings in Tobacco"
675:of candy, soft drinks (e.g.
904:Pakistan Journal of Zoology
610:. Its chemical formula is C
1112:
647:. It is combustible, with
15:
543:
452:
447:
360:
340:
305:
63:
51:
46:
37:
28:
838:10.1002/hlca.19630460506
510:Precautionary statements
16:Not to be confused with
1066:(2011), 5:3; 202-207.
826:Helvetica Chimica Acta
596:methyl 2-aminobenzoate
57:Methyl 2-aminobenzoate
643:. It is insoluble in
395:151.165
935:10.1056/NEJMc1403015
865:10.1135/cccc19960751
709:. It is obtained by
53:Preferred IUPAC name
24:Methyl anthranilate
18:Menthyl anthranilate
626:Chemical properties
600:carbomethoxyaniline
588:Methyl anthranilate
25:
696:hydroxycitronellal
671:. It is used for
576:Infobox references
352:COC(=O)c1c(N)cccc1
23:
1035:10.1021/cr200478h
970:978-1-870228-24-4
962:978-0-9608752-8-3
928:(23): 2250–2252.
584:Chemical compound
582:
581:
496:Hazard statements
403:colorless liquid
279:CompTox Dashboard
105:Interactive image
1103:
1070:
1060:
1054:
1053:
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1029:(6): 3550–3577.
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1002:
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994:978-085404-824-3
978:
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878:
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832:(5): 1480–1513.
821:
641:propylene glycol
608:anthranilic acid
590:, also known as
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529:
525:
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368:Chemical formula
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1064:Rec. Nat. Prod.
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765:mandarin orange
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805:ethyl butyrate
736:Vitis labrusca
731:Concord grapes
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665:bird repellent
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547:standard state
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524:P305+P351+P338
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1091:Methyl esters
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1086:Anthranilates
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986:0-85404-824-3
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711:diazotization
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653:Concord grape
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439:Boiling point
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429:Melting point
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177:ECHA InfoCard
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145:ChEMBL1493986
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1046:. Retrieved
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925:
921:
911:
906:48.5 (2016).
903:
898:
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852:
846:
829:
825:
819:
745:black locust
734:
728:
700:
688:Schiff bases
685:
662:
645:paraffin oil
633:fluorescence
629:
599:
595:
591:
587:
586:
487:
454:
64:Identifiers
1048:20 November
797:ylang ylang
719:Diels-Alder
649:flash point
535:Flash point
482:Signal word
423:1.168 g/cm
413:grape-like
400:Appearance
361:Properties
183:100.004.667
125:CHEBI:73244
1080:Categories
859:(5): 751.
811:References
781:strawberry
733:and other
725:Occurrence
677:grape soda
466:Pictograms
391:Molar mass
267:981I0C1E5W
156:ChemSpider
92:3D model (
71:CAS Number
1023:Chem. Rev
1006:Aurantiol
692:aldehydes
673:flavoring
528:P337+P313
457:labelling
204:205-132-4
196:EC Number
1043:22443517
944:24805984
793:galangal
789:wisteria
785:tuberose
753:gardenia
741:bergamot
681:Grāpples
669:Kool-Aid
602:, is an
448:Hazards
165:13858096
81:134-20-3
1096:Flavors
773:oranges
757:jasmine
749:champak
707:benzyne
637:ethanol
569:what is
567: (
488:Warning
419:Density
385:
234:PubChem
1041:
992:
984:
968:
960:
942:
795:, and
769:neroli
564:verify
561:
345:SMILES
222:C20634
136:ChEMBL
47:Names
779:oil,
761:lemon
703:aryne
690:with
604:ester
598:, or
310:InChI
116:ChEBI
94:JSmol
1050:2022
1039:PMID
990:ISBN
982:ISBN
966:ISBN
958:ISBN
940:PMID
803:and
659:Uses
639:and
520:P280
516:P264
502:H319
409:Odor
258:UNII
247:8635
213:KEGG
1068:pdf
1031:doi
1027:112
930:doi
926:370
861:doi
834:doi
777:rue
606:of
455:GHS
284:EPA
237:CID
1082::
1037:.
1025:.
1021:.
988:,
964:,
938:.
924:.
920:.
873:^
857:61
855:.
830:46
828:.
807:.
791:,
787:,
783:,
775:,
771:,
767:,
763:,
759:,
755:,
751:,
747:,
743:,
705:,
698:.
618:NO
594:,
592:MA
526:,
522:,
518:,
459::
381:NO
1052:.
1033::
946:.
932::
867:.
863::
840:.
836::
715:2
620:2
616:9
614:H
612:8
559:N
383:2
379:9
377:H
375:8
373:C
286:)
282:(
96:)
20:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
