Showing Compound 3,4-Dihydroxybenzaldehyde (FDB012060)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:58 UTC

Update date

2019-11-26 03:06:06 UTC

Primary ID

FDB012060

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3,4-Dihydroxybenzaldehyde

Description

Protocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus .

CAS Number

139-85-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
1,2-Dihydroxy-4-formylbenzene	ChEBI
3,4-Dihydroxybenzenecarbonal	ChEBI
4-Formyl-1,2-benzenediol	ChEBI
4-Formyl-1,2-dihydroxybenzene	ChEBI
Protocatechualdehyde	ChEBI
Protocatechuic aldehyde	ChEBI
Protocatechualdehyde, 3H-labeled	MeSH
Rancinamycin IV	MeSH
Protocatechualdehyde, formyl-14C-labeled	MeSH
3,4-Dihydroxybenzaldehyde	HMDB
Protocatechualdehyde, 8CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	14.3 g/L	ALOGPS
logP	0.89	ALOGPS
logP	1.08	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	7.46	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.6 m³·mol⁻¹	ChemAxon
Polarizability	12.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C7H6O3

IUPAC name

3,4-dihydroxybenzaldehyde

InChI Identifier

InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H

InChI Key

IBGBGRVKPALMCQ-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=C(C=O)C=C1O

Average Molecular Weight

138.1207

Monoisotopic Molecular Weight

138.031694058

Classification

Description

Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
Catechol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydroxybenzaldehyde (CHEBI:50205 )
an aryl aldehyde (CPD-7616 )

Ontology

Disposition

Biological location:

Biofluid and excreta:

Urine

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 60.87%; H 4.38%; O 34.75%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	[neutral] lmax 220 (e 9500) (95% EtOH) (Derep)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	3,4-Dihydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052r-2900000000-fd0d28650a72226166e6	Spectrum
Predicted GC-MS	3,4-Dihydroxybenzaldehyde, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00yi-8690000000-16ccc54dcf22361cffb1	Spectrum
Predicted GC-MS	3,4-Dihydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0002-0040900010-522c055741661bbc5ba8	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0002-0040900010-522c055741661bbc5ba8	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0002-0040900010-522c055741661bbc5ba8	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-002r-0905000000-7987816fb8648b0eea18	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0900000000-aa91c9c469ec39450435	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0900000000-25b5b2bc87af9df04e91	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0900000000-03d9e2dbe57c9bcfb9ab	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-002r-0905000000-7987816fb8648b0eea18	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0900000000-aa91c9c469ec39450435	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0900000000-25b5b2bc87af9df04e91	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-aa91c9c469ec39450435	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-25b5b2bc87af9df04e91	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-db13978cfcbc33c6da32	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-ed3a0258f14e4361b25c	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-9200000000-cdb54c91531419396213	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-db13978cfcbc33c6da32	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-ed3a0258f14e4361b25c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-9200000000-cdb54c91531419396213	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-882b8375384be94a3491	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-25b2a170eaf9dd74c4a0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kw4-9300000000-e349b638bc98dcdf0ade	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-882b8375384be94a3491	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-25b2a170eaf9dd74c4a0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kw4-9300000000-e349b638bc98dcdf0ade	2015-05-27	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

723

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HCW75-Q:HCW75-Q

EAFUS ID

Not Available

Dr. Duke ID

PROTOCATECHUIC-ALDEHYDE|3,4-DIHYDROXYBENZALDEHYDE|PROTOCATECHUALDEHYDE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1040061

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

723

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti aggregant			DUKE
anti coagulant	50249	An agent that prevents blood clotting.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
dry	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medical	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
almond	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.