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37520 Sigma-Aldrich

3,4-Dihydroxybenzaldehyde

purum, ≥97.0% (HPLC)

Synonym: Protocatechualdehyde

  • CAS Number 139-85-5

  • Linear Formula (HO)2C6H3CHO

  • Molecular Weight 138.12

  •  Beilstein/REAXYS Number 774381

  •  EC Number 205-377-7

  •  MDL number MFCD00003370

  •  PubChem Substance ID 329755658

  •  NACRES NA.22

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Properties

Related Categories Aldehydes, Building Blocks, C7, Carbonyl Compounds, Chemical Synthesis,
Quality Level   100
grade   purum
assay   ≥97.0% (HPLC)
mp   150-155 °C
  150-157 °C (lit.)
SMILES string   Oc1ccc(C=O)cc1O
InChI   1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
InChI key   IBGBGRVKPALMCQ-UHFFFAOYSA-N

Description

General description

3,4-Dihydroxybenzaldehyde has been recognized as one of the antifungal compound extracted from the outer skin of green Cavendish bananas. It can be synthesized from catechol via Fries rearrangement.

3,4-Dihydroxybenzaldehyde is reported as bioactive compound which inhibits the H2O2-induced apoptosis of granulosa cells. Oxidation of 3,4-dihydroxybenzaldehyde on glassy carbon electrodes is reported to afford stable redox-active electropolymerized films containing a quinone moity.

Application

3,4-Dihydroxybenzaldehyde (Protocatechualdehyde) may be employed as starting reagent for the synthesis of 4-vinylbenzocrown ether.

3,4-Dihydroxybenzaldehyde may be used for the surface modification of nanocrystalline TiO2 particles. Electrodeposited layer of 3,4-dihydroxybenzaldehyde may be used as effective redox mediator during oxidation of NADH at graphene. It may be used in the preparation of new diSchiff base ligands, which forms di-, tri- and tetranuclear Co(II) and Cu(II) complexes.

Packaging

100 g in glass bottle

25 g in poly bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 37520.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
UL0380000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles
Peer-Reviewed Papers
15

References

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