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CS-W001157 4
Total: USD 88.00

Isovanillin

  • CAS No. 621-59-0

  • Cat. No. CS-W009023
  • Purity≥98%
  • MDL No.MFCD00003369

*For research and further manufacturing use only, not for direct human use.

Isovanillin|CS-W009023

Structure of 621-59-0

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General Information

  • CAS No. 621-59-0
  • Cat. No. CS-W009023
  • Purity ≥98%
  • MDL No. MFCD00003369
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈O₃
  • Molecular Weight None
  • Synonym(s) 3-Hydroxy-4-methoxybenzaldehyde
  • SMILES O=CC1=CC=C(OC)C(O)=C1

Description

3-Hydroxy-4-methoxybenzaldehyde on condensation with furan-2-carboxylic acid hydrazide and thiophene-2-carboxylic acid hydrazide yields Schiff-bases. It undergoes condensation reaction with1-azabicyclo[2.2.2]octan-3-one to give (Z)-2-(3-hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one.3-Hydroxy-4-methoxybenzaldehyde was used as starting reagent during the two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 and glycitein synthesis.

Application

Isovanillin serves as a versatile phenolic aldehyde building block in synthetic organic chemistry, enabling efficient access to bioactive heterocycles and natural product analogs. Its ortho-hydroxyl and aldehyde functionalities support direct condensation reactions, including Mannich-type cyclizations and Schiff base formation, with predictable regiochemistry. The compound exhibits good bench stability and is readily purified by recrystallization or chromatography, facilitating its use in multi-step synthesis workflows.

Synthesis

  • Route1
    • In-stock
      Protocatechualdehyde|CS-W009195
      139-85-5
    • null|null
      74-88-4
    • ~83%
    • In-stock
      Isovanillin|CS-W009023
      621-59-0

    References

    • Japan Tobacco Inc. Patent: US6509352 B1, 2003 ;
  • Route2

    References

    • Jempty, Thomas C.; Gogins, Kitty A. Z.; Mazur, Yehuda; Miller, Larry L. Journal of Organic Chemistry, 1981 , vol. 46, # 22 p. 4545 - 4551
  • Route3
    • 3-(Allyloxy)-4-methoxybenzaldehyde|CS-0359583
      18075-40-6
    • ~93%
    • In-stock
      Isovanillin|CS-W009023
      621-59-0

    References

    • Nawghare; Sakate; Lokhande Journal of Heterocyclic Chemistry, 2014 , vol. 51, # 2 p. 291 - 302

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P271-P261-P280-P305+P351+P338-P312-P337+P313-P403+P233-P501

Quality Control

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Computational Chemistry Data

  • TPSA   46.53
  • LogP   1.2133
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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