Cannabis Compound Database: Showing Compound Card for Protocatecuic aldehyde (CDB006366)

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Record Information

Version

1.0

Created at

2020-11-02 22:39:11 UTC

Updated at

2022-12-13 19:31:27 UTC

CannabisDB ID

CDB006366

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Protocatecuic aldehyde

Description

3,4-Dihydroxybenzaldehyde, also known as protocatechualdehyde or 1,2-dihydroxy-4-formylbenzene, 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. 3,4-Dihydroxybenzaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxybenzaldehyde is an almond, bitter, and dry tasting compound. Outside of the human body, 3,4-Dihydroxybenzaldehyde is found, on average, in the highest concentration within vinegars and grape wines. 3,4-Dihydroxybenzaldehyde has also been detected, but not quantified in, several different foods, such as orange bell peppers, common wheats, spelts, horseradish tree, and muskmelons. This could make 3,4-dihydroxybenzaldehyde a potential biomarker for the consumption of these foods.

Structure

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

Synonyms

Value	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

Chemical Formula

C₇H₆O₃

Average Molecular Weight

138.1207

Monoisotopic Molecular Weight

138.031694058

IUPAC Name

3,4-dihydroxybenzaldehyde

Traditional Name

3,4-dihydroxybenzaldehyde

CAS Registry Number

Not Available

SMILES

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

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

Chemical Taxonomy

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

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Protocatecuic aldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052r-2900000000-fd0d28650a72226166e6	Spectrum
Predicted GC-MS	Protocatecuic aldehyde, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00yi-8690000000-16ccc54dcf22361cffb1	Spectrum
Predicted GC-MS	Protocatecuic aldehyde, 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

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.00458 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.00208 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.00295 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.0017 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.00149 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.00181 mg/g dry wt	David S. Wishart,...	details