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2D Structure
Also known as: 4-hydroxy-3-methoxybenzaldehyde, 121-33-5, Vanillaldehyde, Vanillic aldehyde, P-vanillin, Lioxin
Molecular Formula
C8H8O3
Molecular Weight
152.15  g/mol
InChI Key
MWOOGOJBHIARFG-UHFFFAOYSA-N
FDA UNII
CHI530446X

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
4-hydroxy-3-methoxybenzaldehyde
2.1.2 InChI
InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
2.1.3 InChI Key
MWOOGOJBHIARFG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=C(C=CC(=C1)C=O)O
2.2 Other Identifiers
2.2.1 UNII
CHI530446X
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-hydroxy-3-methoxybenzaldehyde

2. 5-bromovanillin

3. 5-chlorovanillin

4. Vanillaldehyde

5. Vanillin, Sodium Salt

2.3.2 Depositor-Supplied Synonyms

1. 4-hydroxy-3-methoxybenzaldehyde

2. 121-33-5

3. Vanillaldehyde

4. Vanillic Aldehyde

5. P-vanillin

6. Lioxin

7. Vanilla

8. Vanilline

9. Benzaldehyde, 4-hydroxy-3-methoxy-

10. 3-methoxy-4-hydroxybenzaldehyde

11. 4-hydroxy-m-anisaldehyde

12. Zimco

13. P-hydroxy-m-methoxybenzaldehyde

14. 2-methoxy-4-formylphenol

15. 4-hydroxy-3-methoxy-benzaldehyde

16. Methylprotocatechuic Aldehyde

17. Vanilin

18. 4-formyl-2-methoxyphenol

19. Vanillin (natural)

20. 4-hydroxy-5-methoxybenzaldehyde

21. M-anisaldehyde, 4-hydroxy-

22. Protocatechualdehyde, Methyl-

23. Rhovanil

24. Fema No. 3107

25. Vanillin (nf)

26. Protocatechualdehyde 3-methyl Ether

27. Vaniline

28. Nsc 15351

29. Vanillin [nf]

30. M-methoxy-p-hydroxybenzaldehyde

31. Vanillin Melting Point Standard

32. Mfcd00006942

33. Nsc-15351

34. Nsc-48383

35. Nsc-403658

36. Chembl13883

37. Chebi:18346

38. Nplc-0145

39. 4-hydroxy-3-methoxy-benzyldehyde

40. Chi530446x

41. 4-hydroxy,3-methoxy-benzaldehyde

42. Ncgc00091645-03

43. 4-hydroxy-3-methoxybenzaldehyde (vanillin)

44. Dsstox_cid_1969

45. Wln: Vhr Dq Co1

46. H-0264

47. Dsstox_rid_76433

48. Dsstox_gsid_21969

49. Vanillin [usan]

50. Oleoresin Vanilla

51. Vanilla Oleoresin

52. Mfcd08702848

53. Cas-121-33-5

54. Ccris 2687

55. Hsdb 1027

56. Einecs 204-465-2

57. Brn 0472792

58. Unii-chi530446x

59. Ai3-00093

60. Nat.vanillin

61. 3-methoxy-4-hydroxy-benzaldehyde

62. Vanillin, Natural

63. Oleo-resins Vanilla

64. V55

65. Vanillin Sodium Salt

66. Vanillininclusioncomplex

67. Vanillin [fhfi]

68. Vanillin [hsdb]

69. Vanillin [inci]

70. Oleo-resins Vanilla-bean

71. Vanillin [fcc]

72. 4-hydroxy-3-methoxybenzaldehyde(vanilline)

73. Vanillin [ii]

74. Vanillin [mi]

75. Vanillin [vandf]

76. Vanillin Inclusion Complex

77. Vanillin-[methoxy-13c]

78. Methyl-protocatechualdehyde

79. Vanillin [mart.]

80. Bmse000343

81. Bmse000597

82. Bmse010006

83. Methylprotcatechuic Aldehyde

84. Vanillin [usp-rs]

85. Vanillin [who-dd]

86. Ec 204-465-2

87. Schembl1213

88. 4-08-00-01763 (beilstein Handbook Reference)

89. Mls002303069

90. Bidd:er0330

91. Vanillin, Puriss., 99.5%

92. Gtpl6412

93. Sgcut00016

94. 4-hydroxy 3-methoxybenzaldehyde

95. Vanillin [ep Monograph]

96. Dtxsid0021969

97. Fema 3107

98. Vanilla Oleoresin (vanilla Spp)

99. 3-methoxy-4-hydroxy Benzaldehyde

100. 4-hydroxy-3-methoxy Benzaldehyde

101. Vanillin, Natural [fhfi]

102. 3-methoxy-4-hydroxy Benzoaldehyde

103. Vanillin, Reagentplus(r), 99%

104. 4-hydroxy-3-(methoxy)benzaldehyde

105. Hms3651d20

106. Hms3885k07

107. Vanillin, >=97%, Fcc, Fg

108. 4-hydoxy-3-(methyloxy)benzaldehyde

109. Bcp29943

110. Hy-n0098

111. Nsc15351

112. Nsc48383

113. Str01001

114. To_000089

115. Zinc2567933

116. Tox21_113534

117. Tox21_201925

118. Tox21_300352

119. 4-hydoxy-3-(methyloxy)benz Aldehyde

120. Bbl011956

121. Bdbm50177405

122. Methyl Protocatechuic Aldehyde

123. Nsc403658

124. S3071

125. Stk199262

126. Akos000118929

127. Tox21_113534_1

128. Ccg-266230

129. Cs-w020052

130. Vanillin, Tested According To Ph.eur.

131. Ncgc00091645-01

132. Ncgc00091645-02

133. Ncgc00091645-04

134. Ncgc00091645-05

135. Ncgc00091645-07

136. Ncgc00254468-01

137. Ncgc00259474-01

138. Vanillin, Natural, >=97%, Fcc, Fg

139. Ac-10370

140. Bp-10602

141. Nci60_001085

142. Smr000156285

143. Sy224451

144. Vanillin 1000 Microg/ml In Acetonitrile

145. Vanillin, Jis Special Grade, >=98.0%

146. Vanillin, Vetec(tm) Reagent Grade, 98%

147. 3-methoxy-4-hydroxybenzaldehyde (vanillin)

148. Db-003805

149. Am20060497

150. Ft-0618639

151. Ft-0669738

152. Ft-0675778

153. H0264

154. Sw219190-1

155. V0080

156. Vanillin (3-methoxy-4-hydroxy- Benzaldehyde)

157. A19444

158. C00755

159. D00091

160. Q33495

161. Vanillin (83 Degrees C) Melting Point Standard

162. 4-hydroxy-3-methoxy-benzaldehyde-5-chlorovanillin

163. 4-hydroxy-3-methoxybenzaldehyde (acd/name 4.0)

164. Ac-907/21098004

165. Q-100102

166. Vanillin, Tracecert(r), Certified Reference Material

167. F2190-0587

168. Vanillin, European Pharmacopoeia (ep) Reference Standard

169. 1-(aminomethyl)-cyclopropanecarboxylicacidethylester

170. Mettler-toledo Calibration Substance Me 51143093, Vanillin

171. Vanillin, United States Pharmacopeia (usp) Reference Standard

172. Nsc 15351;nsc-15351; Nsc15351 Pound>>4-hydroxy-3-methoxybenzaldehyde

173. Vanillin, Pharmaceutical Secondary Standard; Certified Reference Material

174. Vanillin Melting Point Standard, United States Pharmacopeia (usp) Reference Standard

175. Mettler-toledo Calibration Substance Me 51143093, Vanillin, Traceable To Primary Standards (lgc)

176. Vanillin Melting Point Standard, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 152.15 g/mol
Molecular Formula C8H8O3
XLogP31.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass152.047344113 g/mol
Monoisotopic Mass152.047344113 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count11
Formal Charge0
Complexity135
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 THE CHOLERETIC PROPERTIES & MECHANISM OF COUMARIN COMPD & PHENOLIC COMPD WERE STUDIED BY EXAMINING THEIR EFFECTS ON PARAMETERS SUCH AS BILE FLOW, BILE ACIDS, ELECTROLYTES, & BILIARY METABOLITES. VANILLIN ACCELERATED BILE SECRETION.

TAKEDA ET AL; J PHARMACOBIO-DYN 4(9) 724 (1981)


VET: ...AS AN AEROSOLED AID IN GETTING EWES TO SUCKLE ORPHAN LAMBS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 634


EXPL THER Methotrexate (MTX), a chemotherapeutic agent used to treat cancer, produces cytogenetic damage and has a cytostatic effect in a variety of test systems. Several antigenotoxic agents have been studied in various in vitro and in vivo systems. However, data are limited regarding their ability to modulate MTX-induced genotoxicity. In the present study, vanillin (VA) and chlorophyllin (CHL) were used as antigenotoxic agents to study their ability to minimize the DNA damage caused by MTX. Exponentially growing V79 Chinese hamster lung cells were treated with MTX at five different concentrations (5-100 ug/mL) with S9 activation for 6 h and post-treated with two concentrations of either VA (50 or 100 ug/mL) or CHL (50 or 100 ug/mL) for 40 h. Cytochalasin B was added for the micronucleus (MN) assay along with antigenotoxic agents to evaluate MN in binucleated cells. Chromosomal aberrations were also evaluated in parallel cultures. Results indicate that MTX alone induced a dose-dependent decrease in the nuclear division index (NDI) and the mitotic index (MI). A significant increase in percent micronucleated binucleated cells (MNBN) and percent aberrant cells (Abs) was observed. Studies using VA as an antigenotoxic agent showed a decrease in the number of MNBN (26.3-83.1%) and Abs (16.0-87.5%) with the addition of either 50 or 100 micrograms VA/ml. The addition of CHL also significantly reduced the number of MNBN (53.0-91.5%) at both concentrations tested. Chromosomal aberrations were also significantly reduced (41.0-83.0). These studies indicate that both VA and CHL are capable of effectively minimizing MTX-induced chromosomal damage.

Keshava C et al; Teratog Carcinog Mutagen 17 (6): 313-26 (1997-98)


EXPL THER Vanillin is a well-known food and cosmetic additive and has antioxidant and antimutagenic properties. It has also been suggested to have antifungal activity against major human pathogenic fungi, although it is not very effective. In this study, the antifungal activities of vanillin and 33 vanillin derivatives against the human fungal pathogen Cryptococcus neoformans, the main pathogen of cryptococcal meningitis in immunocompromised patients, were investigated. We found a structural correlation between the vanillin derivatives and antifungal activity, showing that the hydroxyl or alkoxy group is more advantageous than the halogenated or nitrated group in benzaldehyde. Among the vanillin derivatives with a hydroxyl or alkoxy group, o-vanillin and o-ethyl vanillin showed the highest antifungal activity against C. neoformans. o-Vanillin was further studied to understand the mechanism of antifungal action. We compared the transcriptome of C. neoformans cells untreated or treated with o-vanillin by using RNA sequencing and found that the compound caused mitochondrial dysfunction and triggered oxidative stress. These antifungal mechanisms of o-vanillin were experimentally confirmed by the significantly reduced growth of the mutants lacking the genes involved in mitochondrial functions and oxidative stress response.

PMID:24586538 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3930674 Kim JH et al; PLoS One 9 (2): e89122 (2014)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)


Antimutagenic Agents

Agents that reduce the frequency or rate of spontaneous or induced mutations independently of the mechanism involved. (See all compounds classified as Antimutagenic Agents.)


Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)


5.2 Absorption, Distribution and Excretion

... When vanillin was fed to rats at doses of 100 mg/kg most metabolites were excreted in the urine within 24 hr....

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 929


5.3 Metabolism/Metabolites

... Vanillin administered intraperitoneally to rats gave rise to a number of urinary products; chief among these was vanillic acid in both free and conjugated forms. Other metabolites were conjugated vanillin, conjugated vanillyl alcohol, and catechol.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 929


YIELDS PROTOCATECHUALDEHYDE PROBABLY BY MICROORGANISMS; VANILLIN-4-BETA-D-GLUCOSIDE IN BEAN & JAPONICA; VANILLIN-4-BETA-D-GLUCURONIDE IN RABBITS. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. V-2


... When vanillin was fed to rats at doses of 100 mg/kg most metabolites were excreted in urine within 24 hr, chiefly as glucuronide and/or sulfate conjugates, although the acids formed were also excreted free and as their glycine conjugates. In 48 hr 94% of the dose was accounted for, 7% as vanillin, 19% as vanillyl alcohol, 47% as vanillic acid, 10% as vanilloyglycine, 8% as catechol, 2% as 4-methylcatechol, 0.5% as guaiacol , and 0.6% as 4-methylguaiacol.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 929


YIELDS VANILLIC ACID IN MAN. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. V-2