Showing Compound 4-Hydroxybenzaldehyde (FDB010504)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:09 UTC

Update date

2019-11-26 03:03:39 UTC

Primary ID

FDB010504

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Hydroxybenzaldehyde

Description

4-Hydroxybenzaldehyde, also known as 4-formylphenol, 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. 4-Hydroxybenzaldehyde exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzaldehyde is a sweet, almond, and balsam tasting compound. 4-Hydroxybenzaldehyde is found, on average, in the highest concentration within a few different foods, such as vinegar, oats (Avena sativa), and beer. 4-Hydroxybenzaldehyde has also been detected, but not quantified in, several different foods, such as horseradish trees (Moringa oleifera), chayotes (Sechium edule), peanuts (Arachis hypogaea), yardlong beans (Vigna unguiculata ssp. sesquipedalis), and mixed nuts. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Hydroxybenzaldehyde.

CAS Number

123-08-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-Formylphenol	ChEBI
p-Formylphenol	ChEBI
p-Hydroxybenzaldehyde	ChEBI
4-Hydroxy-benzaldehyde	HMDB
4-Hydroxybenzenecarbonal	HMDB
P-Hydroxy-benzaldehyde	HMDB
p-Oxybenzaldehyde	HMDB
Parahydroxybenzaldehyde	HMDB
Usaf m-6	HMDB
Para-hydroxybenzaldehyde	MeSH, HMDB
4-Hydroxybenzaldehyde	PhytoBank
4-hydroxy-Benzaldehyde	biospider
4-Hydroxybenzaldehyde, homopolymer	biospider
Benzaldehyde, 4-hydroxy-	biospider
Benzaldehyde, 4-hydroxy-, homopolymer	biospider
Benzaldehyde, p-hydroxy-	biospider
HBA	biospider
P-hydroxybenzaldehyde	biospider
P-oxybenzaldehyde	biospider
P-oxybenzaldehyde;p-hydroxy-benzaldehyde	biospider
PHB	biospider

Predicted Properties

Property	Value	Source
Water Solubility	9.51 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.38	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.62 m³·mol⁻¹	ChemAxon
Polarizability	11.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C7H6O2

IUPAC name

4-hydroxybenzaldehyde

InChI Identifier

InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H

InChI Key

RGHHSNMVTDWUBI-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=C(C=O)C=C1

Average Molecular Weight

122.1213

Monoisotopic Molecular Weight

122.036779436

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxybenzaldehyde (CHEBI:17597 )
a small molecule (4-HYDROXYBENZALDEHYDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Animal

Plant:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Prostate cancer

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	Solid
Physical Description	Not Available
Mass Composition	C 68.85%; H 4.95%; O 26.20%	DFC
Melting Point	Mp 115-116°	DFC
Boiling Point	Not Available
Experimental Water Solubility	8.45 mg/mL at 25 oC	JIN,LJ et al. (1998)
Experimental logP	1.35	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 7.62 (25°, H2O)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	330 (e 6600) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00di-9500000000-2c1739a8a2bc288e4a5c	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00di-8900000000-4eff34096f6bd4f30d10	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00di-9800000000-c8646d08ef8e23a3d49b	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00di-8900000000-60621d4d9871b2d7587d	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-05i0-1970000000-7ef151eab685361413a6	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00b9-1940000000-fa6b812457f26dce7720	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00b9-2940000000-0bfc68ade3f25f6ba1f2	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00b9-2940000000-b50ed8954cb10b92a30b	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00b9-2930000000-671031e52722de3402ec	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00di-8900000000-4eff34096f6bd4f30d10	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00di-9800000000-c8646d08ef8e23a3d49b	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00di-8900000000-60621d4d9871b2d7587d	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-05i0-1970000000-7ef151eab685361413a6	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00b9-1940000000-fa6b812457f26dce7720	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00b9-2940000000-0bfc68ade3f25f6ba1f2	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00b9-2940000000-b50ed8954cb10b92a30b	Spectrum
GC-MS	4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrum	splash10-00b9-2930000000-671031e52722de3402ec	Spectrum
Predicted GC-MS	4-Hydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6900000000-ea309e8826550692ddeb	Spectrum
Predicted GC-MS	4-Hydroxybenzaldehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-8900000000-781df730e85ee6b33891	Spectrum
Predicted GC-MS	4-Hydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0900000000-99136b39c7ec11a7bbca	Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-00di-0900000000-ab4c213ba9a645517aa3	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9300000000-7a1d8d268b763ce71331	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-002g-9000000000-e9050639f16e3b6d7939	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-00di-0900000000-27effb3a35bdb0d72310	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-00di-1900000000-731f917249c17a761e0f	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-00dj-5900000000-c46a92738e14de26b66c	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-006t-9500000000-7f1f8c64931b0dc6f66f	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0002-9100000000-39037b9523c5f3c7ed6c	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0002-9000000000-06c809ed4b25327e8b09	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-002b-9000000000-b93cdaad48fe246028dd	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-002b-9000000000-16e7fae11656d4e6cd8a	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0fba-9000000000-96924ab5b95b0d4fb857	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-298ab6a83ac989405983	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-12ad1640340af91bc8e8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0036-9000000000-ddc48e682b255bd53c5e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-785058db9c1fbc1b5950	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-c22365c838c065b99ed8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0100-9300000000-491fc6287b2479ddc1a6	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-298ab6a83ac989405983	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-12ad1640340af91bc8e8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0036-9000000000-ddc48e682b255bd53c5e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-785058db9c1fbc1b5950	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-c22365c838c065b99ed8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0100-9300000000-491fc6287b2479ddc1a6	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

725

DrugBank ID

DB03560

HMDB ID

HMDB11718

CRC / DFC (Dictionary of Food Compounds) ID

FBR96-V:FBR96-V

EAFUS ID

1724

Dr. Duke ID

4-HYDROXYBENZALDEHYDE|P-HYDROXYBENZALDEHYDE

BIGG ID

Not Available

KNApSAcK ID

C00002657

HET ID

HBA

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1040191

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

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
allelochemic			DUKE
anti feedant			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
tyrosinase inhibitor	59997	Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty	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.
balsam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.