All Photos(3)

37520

Sigma-Aldrich

3,4-Dihydroxybenzaldehyde

purum, ≥97.0% (HPLC)

Synonym(s):
Protocatechualdehyde
Linear Formula:
(HO)2C6H3CHO
CAS Number:
Molecular Weight:
138.12
Beilstein:
774381
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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

Packaging

25 g in poly bottle
100 g in glass 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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

3, 4-dihydroxybenzaldehyde, a fungistatic substance from green Cavendish bananas.
Mulvena D, et al.
Phytochemistry, 8(2), 393-395 (1969)
Tatjana D Savić et al.
Physical chemistry chemical physics : PCCP, 16(38), 20796-20805 (2014-08-29)
The surface modification of nanocrystalline TiO2 particles (45 Å) with catecholate-type ligands having different electron donating/electron withdrawing substituent groups, specifically 3-methylcatechol, 4-methylcatechol, 3-methoxycatechol, 3,4-dihydroxybenzaldehyde and 4-nitrocatechol, was found to alter the optical properties of nanoparticles in a similar way to...
Nicole L Ritzert et al.
Faraday discussions, 172, 27-45 (2014-11-27)
Over the past decade, there has been a great deal of interest in graphene with regards to its electrochemical behavior. Previous studies have focused on understanding fundamental processes such as charge transfer and molecular transport at the graphene-electrolyte interface as...
Ryohei Kono et al.
Acta histochemica et cytochemica, 47(3), 103-112 (2014-10-17)
Granulosa cells form ovarian follicles and play important roles in the growth and maturation of oocytes. The protection of granulosa cells from cellular injury caused by oxidative stress is an effective therapy for female infertility. We here investigated an effective...
Synthesis of 4'-vinylbenzocrown ethers.
Smid J, et al.
Organic Prep. and Proc. Int., 8(4), 193-196 (1976)

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