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CAS 134-20-3 manufacturers and suppliers on PharmaCompass

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CAS 134-20-3
Also known as: Methyl 2-aminobenzoate, 134-20-3, 2-aminobenzoic acid methyl ester, Nevoli oil, Methyl o-aminobenzoate, Methylanthranilate
Molecular Formula
C8H9NO2
Molecular Weight
151.16  g/mol
InChI Key
VAMXMNNIEUEQDV-UHFFFAOYSA-N
FDA UNII
981I0C1E5W

methyl anthranilate is a natural product found in Citrus hystrix, Hesperis matronalis, and other organisms with data available.
1 2D Structure

CAS 134-20-3

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl 2-aminobenzoate
2.1.2 InChI
InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
2.1.3 InChI Key
VAMXMNNIEUEQDV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC(=O)C1=CC=CC=C1N
2.2 Other Identifiers
2.2.1 UNII
981I0C1E5W
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Methyl 2-aminobenzoate

2. 134-20-3

3. 2-aminobenzoic Acid Methyl Ester

4. Nevoli Oil

5. Methyl O-aminobenzoate

6. Methylanthranilate

7. Anthranilic Acid Methyl Ester

8. O-carbomethoxyaniline

9. 2-carbomethoxyaniline

10. 2-(methoxycarbonyl)aniline

11. Benzoic Acid, 2-amino-, Methyl Ester

12. Neroli Oil, Artifical

13. Neroli Oil, Artificial

14. Anthranilic Acid, Methyl Ester

15. O-methyl Anthranilate

16. Fema No. 2682

17. O-aminobenzoic Acid Methyl Ester

18. Methyl Antranilate

19. Benzoic Acid, Amino-, Methyl Ester

20. Nsc 3109

21. Methylester Kyseliny Anthranilove

22. O-amino Methyl Benzoate

23. Mfcd00007710

24. 2-aminobenzoic Acid-methyl Ester

25. Chebi:73244

26. O-aminobenzoic Acid, Methyl Ester

27. 2-amino-benzoic Acid Methyl Ester

28. 981i0c1e5w

29. Methyl Ester Of O-aminobenzoic Acid

30. Nsc-3109

31. Methyl 2-aminobenzoate (methyl Anthranilate)

32. Dsstox_cid_5567

33. Dsstox_rid_77832

34. Dsstox_gsid_25567

35. Amino Methyl Benzoate, O-

36. Cas-134-20-3

37. Methyl Anthranilate (natural)

38. Methyl-2-aminobenzoate

39. Ccris 1349

40. Hsdb 1008

41. Einecs 205-132-4

42. Epa Pesticide Chemical Code 128725

43. Brn 0606965

44. Methylester Kyseliny Anthranilove [czech]

45. Unii-981i0c1e5w

46. Ai3-01022

47. Fema 2682

48. Carbomethoxyaniline

49. 2-aminobenzoic Acid, Methyl Ester

50. Methyl Aminobenzoate

51. Anthranilic Acid Methyl

52. O-methoxycarbonylaniline

53. Methyl 2-amino-benzoate

54. Wln: Zr Bvo1

55. Acetaminophen 100% Powder

56. Schembl57713

57. Methyl 2-aminobenzoate, 99%

58. Chembl1493986

59. Dtxsid6025567

60. Methyl Anthranilate [mi]

61. Methyl Anthranilate [fcc]

62. Nsc3109

63. 2-amino Benzoic Acid Methyl Ester

64. Natural Mandarin Pettigrain F.d.

65. Natural Methyl Anthranilate

66. Methyl Anthranilate [fhfi]

67. Methyl Anthranilate [hsdb]

68. Methyl Anthranilate [inci]

69. Zinc157525

70. Methyl Anthranilate [vandf]

71. Methyl Anthranilate [mart.]

72. Str00871

73. Tox21_201657

74. Tox21_300347

75. Methyl Anthranilate [who-dd]

76. Methyl Ester Of O-amino Benzoic Acid

77. Stk045541

78. Akos000119222

79. Am10669

80. Cs-w019645

81. Methyl Anthranilate, >=98%, Fcc, Fg

82. Ncgc00091409-01

83. Ncgc00091409-02

84. Ncgc00091409-03

85. Ncgc00254347-01

86. Ncgc00259206-01

87. Ac-11600

88. Benzoic Acid Methyl Ester,2-amino

89. Hy-77342

90. Methyl-2-aminobenzoate Methyl Anthranilate

91. 5-nitro-pyridine-2-sulfonylchloride

92. Db-042220

93. Methyl Anthranilate, Natural, >=99%, Fg

94. A0500

95. Ft-0622414

96. C20634

97. D77860

98. Methyl 2-aminobenzoate, Reagentplus(r), >=99%

99. Methyl Anthranilate, Natural (us), >=99%, Fg

100. Q420894

101. W-108288

102. F2141-0131

103. Methyl 2-aminobenzoate, Vetec(tm) Reagent Grade, 98%

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 151.16 g/mol
Molecular Formula C8H9NO2
XLogP31.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass151.063328530 g/mol
Monoisotopic Mass151.063328530 g/mol
Topological Polar Surface Area52.3 Ų
Heavy Atom Count11
Formal Charge0
Complexity147
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPL THER/ Human victims of a massive number of stings have been steadily increasing since the invasion of Africanized honey bees (Apis mellifera) to the United States in 1990. Multiple honey bee stings may result in venom toxicity, leading to renal failure and even death. Here we tested the efficacy of methyl anthranilate as a honey bee repellent during a massive defensive response by Africanized honey bees. An aerosolized solution of 10% methyl anthranilate reduced the number of defensive bee hits to a retreating victim by 95% compared with a water control. One hundred fifty milliliters of the 10% methyl anthranilate solution sprayed onto stationary foam balls covered with black suede leather located 2 m from provoked Africanized colonies received 80% fewer stings than targets treated with water. Methyl anthranilate (100%) delivered through a UV blocking 3 mil polyethylene pouch was 100% effective in preventing Polistes colonization in wildlife observation huts and from the roof overhang of home patios. Although methyl anthranilate was not 100% effective in preventing honey bee stinging, it seemed to reduce number of stings below the average human LD50, indicative of a promising tool for preventing honey bee venom toxicity and wasp colonization.

PMID:19645280 Pankiw T et al; J Med Entomol 46 (4): 782-8 (2009)


5 Pharmacology and Biochemistry
5.1 Metabolism/Metabolites

Substantial evidence has accumulated showing that many esters readily undergo enzymatic hydrolysis into their component alcohols and acids. In the case of methyl anthranilate, there is direct experimental evidence showing that this ester, while only slowly hydrolyzed by artificial gastric or pancreatic juice, was readily hydrolyzed in rat liver homogenate (50% in 26.6 minutes) and rapidly hydrolyzed in a homogenate of rat small intestine mucosa (50% in 2.5 minutes). Methyl anthranilate has also been shown to be completely hydrolyzed (>99% in two hours) in pig liver homogenate; but was more resistant to hydrolysis in pig jejunum homogenate and completely unhydrolysed by a pancreatin preparation. The hydrolysis products of methyl anthranilate are, of course, methyl alcohol and anthranilic acid. Methyl alcohol is readily metabolized via well-known pathways to carbon dioxide and water. Anthranilic acid is a normal metabolite in man and is excreted in the urine, primarily, as o-aminohippuric acid and to a lesser extent as anthranilic acid glucuronide.

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 14- Methyl Anthranilate (134-20-3). Available from, as of November 11, 2003: https://www.inchem.org/documents/jecfa/jecmono/v14je14.htm


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