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Also known as: 55-10-7, Dl-4-hydroxy-3-methoxymandelic acid, 4-hydroxy-3-methoxymandelic acid, 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid, Vanilmandelic acid, 2394-20-9

Molecular Formula

C₉H₁₀O₅

Molecular Weight

198.17 g/mol

InChI Key

CGQCWMIAEPEHNQ-UHFFFAOYSA-N

FDA UNII

0DQI268449

A 3-O-methyl ether of 3,4-dihydroxymandelic acid. It is an end-stage metabolite of CATECHOLAMINES; EPINEPHRINE; and NOREPINEPHRINE.

1 2D Structure

Vanillylmandelic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

2.1.2 InChI

InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)

2.1.3 InChI Key

CGQCWMIAEPEHNQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=C(C=CC(=C1)C(C(=O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

0DQI268449

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4 Hydroxy 3 Methoxymandelic Acid

2. 4-hydroxy-3-methoxymandelic Acid

3. Acid, 4-hydroxy-3-methoxymandelic

4. Acid, Methoxyhydroxymandelic

5. Acid, Vanillylmandelic

6. Acid, Vanilmandelic

7. Methoxyhydroxymandelic Acid

8. Vanilmandelic Acid

2.3.2 Depositor-Supplied Synonyms

1. 55-10-7

2. Dl-4-hydroxy-3-methoxymandelic Acid

3. 4-hydroxy-3-methoxymandelic Acid

4. 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic Acid

5. Vanilmandelic Acid

6. 2394-20-9

7. Dl-vanillylmandelic Acid

8. (+/-)-vanillylmandelic Acid

9. Vma

10. Benzeneacetic Acid, .alpha.,4-dihydroxy-3-methoxy-

11. Dl-vanillomandelic Acid

12. Hydroxy(4-hydroxy-3-methoxyphenyl)acetic Acid

13. Mandelic Acid, 4-hydroxy-3-methoxy-

14. Adrenaline Related Compound 2

15. Chebi:20106

16. Vanillomandelic Acid

17. 3-methoxy-4-hydroxymandelate

18. Vanillinmandelic Acid

19. 0dqi268449

20. 4-hydroxy-3-methoxy-dl-mandelic Acid

21. (4-hydroxy-3-methoxyphenyl)glycolic Acid

22. 3-methoxy-4-hydroxyphenylhydroxyacetic Acid

23. 3-methoxy-4-hydroxymandelic Acid

24. 4-hydroxy-3-methoxymandelate

25. 4'-hydroxy-3'-methoxymandelic Acid

26. Dl-3-methoxy-4-hydroxymandelic Acid

27. Unii-0dqi268449

28. Benzeneacetic Acid, Alpha,4-dihydroxy-3-methoxy-

29. Einecs 200-224-0

30. Mfcd00004235

31. (y)-vanillylmandelic Acid

32. (?)-vanillylmandelic Acid

33. Lopac0_000602

34. Oprea1_553862

35. Mls002153465

36. Schembl134326

37. (.+/-.)-vanilmandelic Acid

38. Gtpl6645

39. Vanilmandelic Acid [mi]

40. Chembl1256396

41. Fema No. 4660

42. Schembl10085823

43. Dtxsid10861583

44. Hms2235h06

45. Hms3261j06

46. Hms3371d20

47. (+/-)-vanilmandelic Acid

48. Bcp33203

49. Tox21_500602

50. Stl558222

51. 4-hydroxy-3-methoxyphenylglycolic Acid

52. Akos015851906

53. Ccg-204691

54. Lp00602

55. Sdccgsbi-0050584.p002

56. Ncgc00015492-02

57. Ncgc00015492-03

58. Ncgc00015492-04

59. Ncgc00015492-05

60. Ncgc00015492-07

61. Ncgc00093978-01

62. Ncgc00093978-02

63. Ncgc00093978-03

64. Ncgc00261287-01

65. As-62192

66. Smr001230822

67. Db-071947

68. Hy-113121

69. Cs-0059631

70. Eu-0100602

71. Ft-0634243

72. Ft-0669752

73. Ft-0669753

74. H0268

75. S6613

76. ( Inverted Question Mark)-vanillylmandelic Acid

77. C05584

78. D90829

79. H 0131

80. H-6500

81. (+/-)-3-methoxy-4-hydroxymandelic Acid

82. Hydroxy(4-hydroxy-3-methoxyphenyl)acetic Acid #

83. 055h107

84. A817001

85. Dl-.alpha.,4-dihydroxy-3-methoxyphenylacetic Acid

86. Q901369

87. Sr-01000075241

88. 2-(4-hydroxy-3-methoxyphenyl)-2-hydroxyacetic Acid

89. Sr-01000075241-1

90. 2-(4'-hydroxy-3'-methoxyphenyl) 2-hydroxyethanoic Acid

91. Dcd57880-fbee-4ed4-a834-92387d266e8a

92. Dl-4-hydroxy-3-methoxymandelic Acid, Analytical Standard

93. ( Inverted Question Mark)-4-hydroxy-3-methoxymandelic Acid

94. Adrenaline Related Compound 2;4-hydroxy-3-methoxymandelic Acid

95. Dl-4-hydroxy-3-methoxymandelic Acid, >=98% (tlc), Powder

96. Dl-4-hydroxy-3-methoxymandelic Acid (dl-vanillylmandelic Acid)

97. 4-hydroxy-3-methoxy-dl-mandelic Acid;2-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)acetic Acid

98. (+\-)-4-hydroxy-3-methoxymandelic Acid-d3 (ring-d3) Solution, 100 Mug/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₀O₅
Molecular Weight	198.17 g/mol
XLogP3	-0.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	198.05282342 g/mol
Monoisotopic Mass	198.05282342 g/mol
Topological Polar Surface Area	87 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	205
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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