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2D Structure
Also known as: 3-ethoxy-4-hydroxybenzaldehyde, Ethylvanillin, 121-32-4, Bourbonal, Ethylprotal, Ethavan
Molecular Formula
C9H10O3
Molecular Weight
166.17  g/mol
InChI Key
CBOQJANXLMLOSS-UHFFFAOYSA-N
FDA UNII
YC9ST449YJ

Ethyl vanillin is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-ethoxy-4-hydroxybenzaldehyde
2.1.2 InChI
InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3
2.1.3 InChI Key
CBOQJANXLMLOSS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOC1=C(C=CC(=C1)C=O)O
2.2 Other Identifiers
2.2.1 UNII
YC9ST449YJ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-ethoxy-4-hydroxybenzaldehyde

2. Ethylvanillin

2.3.2 Depositor-Supplied Synonyms

1. 3-ethoxy-4-hydroxybenzaldehyde

2. Ethylvanillin

3. 121-32-4

4. Bourbonal

5. Ethylprotal

6. Ethavan

7. Ethovan

8. Vanillal

9. Vanirom

10. Vanilal

11. 4-hydroxy-3-ethoxybenzaldehyde

12. Quantrovanil

13. Rhodiarome

14. Benzaldehyde, 3-ethoxy-4-hydroxy-

15. Ethyl Protal

16. Protocatechuic Aldehyde Ethyl Ether

17. Vanillin, Ethyl-

18. Vanirome

19. 2-ethoxy-4-formylphenol

20. Ethylprotocatechuic Aldehyde

21. 3-ethoxyprotocatechualdehyde

22. Fema No. 2464

23. Arovanillon

24. Vanbeenol

25. Ethyl-vanillin

26. Ethylprotocatechualdehyde-3-ethyl Ether

27. 3-ethoxy-4-hydroxy-benzaldehyde

28. Nsc 1803

29. Mfcd00006944

30. 3-ethoxy-4-hydroxy Benzaldehyde

31. Ethyl Vanillin (nf)

32. Ethyl Vanillin [nf]

33. Nsc-1803

34. Nsc-67240

35. Ethyl Protocatechuic Aldehyde

36. Yc9st449yj

37. Chebi:48408

38. Protocatechuic Aldehyde 3-ethyl Ether

39. J2.006k

40. Ncgc00091583-02

41. Dsstox_cid_1968

42. Wln: Vhr Dq Co2

43. Dsstox_rid_76432

44. Dsstox_gsid_21968

45. Quantrovanil, Vanillal

46. Cas-121-32-4

47. Ccris 1346

48. Hsdb 945

49. Einecs 204-464-7

50. Unii-yc9st449yj

51. Brn 1073761

52. Aethylvanillin

53. Vanillin,ethyl

54. Ai3-00786

55. Ethyl Vaniilin Fcc

56. Ethyl Vanillin, Usan?

57. Ethyl Protocatechualdehyde

58. Ethoxy, Hydroxybenzaldehyde

59. Ec 204-464-7

60. Ethyl Vanillin [ii]

61. Ethyl Vanillin [mi]

62. Schembl30247

63. 3ethoxy-4-hydroxybenzaldehyde

64. Ethyl Vanillin [fcc]

65. Mls002454403

66. Bidd:er0329

67. Ethyl Vanillin [fhfi]

68. Ethyl Vanillin [hsdb]

69. Ethyl Vanillin [inci]

70. 3-ethoxyl-4-hydroxybenzaldhyde

71. 5-ethoxy-4-hydroxybenzaldehyde

72. Vanillin,ethyl [vandf]

73. Chembl508676

74. Ethyl Vanillin [mart.]

75. Dtxsid5021968

76. Ethyl Vanillin [usp-rs]

77. Ethyl Vanillin [who-dd]

78. Fema 2464

79. 3-ethoxy-4-oxidanyl-benzaldehyde

80. Nsc1803

81. 2-ethoxy-4-formyl Phenol

82. Hms2267d23

83. Ethyl Vanillin, Analytical Standard

84. Hy-b0940

85. Nsc67240

86. Zinc2567934

87. Tox21_113535

88. Tox21_202125

89. Tox21_302903

90. 3-ethoxy-4-hydroxybenzaldehyde,(s)

91. Bbl023011

92. S4568

93. Stk353630

94. Ethyl Vanillin, >=98%, Fcc, Fg

95. Akos000119395

96. Am84355

97. Ccg-213720

98. Cs-4409

99. Ps-4030

100. Ncgc00091583-01

101. Ncgc00091583-03

102. Ncgc00091583-04

103. Ncgc00256500-01

104. Ncgc00259674-01

105. Ac-10881

106. Ethyl Proto-catechualdehyde-3-ethyl Ether

107. Nci60_001511

108. Smr001252229

109. Sy011364

110. Db-061895

111. E0050

112. Ft-0615625

113. D01086

114. D70878

115. Ab00949623_05

116. A804713

117. Q416958

118. Sr-01000865052

119. Q-200375

120. Sr-01000865052-2

121. 3-ethoxy-4-hydroxybenzaldehyde, Reagentplus(r), 99%

122. F2190-0622

123. 3-ethoxy-4-hydroxybenzaldehyde, Vetec(tm) Reagent Grade, 99%

124. Ethyl Vanillin, United States Pharmacopeia (usp) Reference Standard

125. Ethyl Vanillin, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 166.17 g/mol
Molecular Formula C9H10O3
XLogP31.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass166.062994177 g/mol
Monoisotopic Mass166.062994177 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count12
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 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

Ethyl (14C)-vanillin was administered to male and female Sprague-Dawley CD rats by gavage in polyethylene glycol solution at single doses of 50, 100, or 200 mg/kg bw. Ethyl vanillin was rapidly absorbed and peak plasma radioactivity occurred within 2 hr after dosing at all dose levels, falling rapidly to undetectable levels within 96 hr. Plasma radioactivity tended to be higher in female than male rats and it was postulated that this might reflect a lower metabolic capacity of female rats. Urinary excretion of radioactivity was rapid and more than 94% of the dose was excreted by this route within 24 hr. Only 1-5% of the dose was excreted in faeces. After 5 days, more than 99% of the administered dose was excreted. No radioactivity was detected in expired air, indicating that the aromatic ring was in a metabolically stable position.

WHO/JECFA; Joint Expert Committee on Food Additives monograph 683. Ethyl vanillin (WHO Food Additives Series 26). Available from, as of June 9, 2015: https://inchem.org/pages/jecfa.html


4.2 Metabolism/Metabolites

A healthy adult male volunteer drank a 235 ml aliquot of a liquid dietary supplement containing an unknown quantity of ethyl vanillin. A concentration of 13 mg ethyl vanillic acid/g creatinine was found in a 12-hour urine sample. The compound was not present in urine collected before exposure.

WHO/JECFA; Joint Expert Committee on Food Additives monograph 683. Ethyl vanillin (WHO Food Additives Series 26). Available from, as of June 9, 2015: https://inchem.org/pages/jecfa.html


Ethyl vanillic acid was identified by GC/MS in the urine of a 9-year old female patient who had received liquid dietary supplementation flavored with vanilla. Other patients excreting this acid were also known to have consumed foodstuffs flavored with ethyl vanillin. Eight different urine samples containing more than 50 mg ethyl vanillic acid/g creatinine were also found to contain small amounts of vanillylmandelic acid. Unchanged ethyl vanillin was not detected in any of the urine samples.

WHO/JECFA; Joint Expert Committee on Food Additives monograph 683. Ethyl vanillin (WHO Food Additives Series 26). Available from, as of June 9, 2015: https://inchem.org/pages/jecfa.html


During urinary organic acid profiling in human subjects, several patients excreted high concentrations of ethyl vanillic acid (3-ethoxy-4-hydroxybenzoic acid) and traces of 3-ethoxy-4-hydroxy- mandelic acid.

WHO/JECFA; Joint Expert Committee on Food Additives monograph 683. Ethyl vanillin (WHO Food Additives Series 26). Available from, as of June 9, 2015: https://inchem.org/pages/jecfa.html


Ethyl (14C)-vanillin was administered to male and female Sprague Dawley CD rats at single oral doses of 50, 100, or 200 mg/kg bw. Rapid metabolism occurred and the principal metabolite at all dose levels was ethyl vanillic acid. Analysis of urine after hydrolysis with glucuronidase and/or sulfatase indicated that the major metabolites were glucuronide or sulfate conjugates of ethyl vanillic acid (56-62%), ethyl vanillyl alcohol (15-20%), and ethyl vanillin (7-12%). A minor proportion of the dose (2-8%) was excreted as the glycine conjugate of vanillic acid (ethyl vanilloyl glycine).

WHO/JECFA; Joint Expert Committee on Food Additives monograph 683. Ethyl vanillin (WHO Food Additives Series 26). Available from, as of June 9, 2015: https://inchem.org/pages/jecfa.html


Early reports indicated that ethyl vanillin was probably metabolized to glucuroethyl vanillin and ethyl vanillic acid, of which some was conjugated with glucuronic and sulfuric acids.

WHO/JECFA; Joint Expert Committee on Food Additives monograph 683. Ethyl vanillin (WHO Food Additives Series 26). Available from, as of June 9, 2015: https://inchem.org/pages/jecfa.html