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

Occurs naturally combined in many glycosides. Constituent of vanillin. Isol. in free state from opium poppy (Papaver somniferum) 4-Hydroxybenzaldehyde reacts with NAD+ and H2O to produce 4-hydroxybenzoate, NADH, and 2 protons. The reaction is catalyzed by 4-hydroxybenzaldehyde dehydrogenase.; ; 4-Hydroxybenzaldehyde is found in the benzoate degradation via hydroxylation, bisphenol A degradation, toluene and xylene degradation, and biosynthesis of phenylpropanoids pathways.

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	HMDB
4-hydroxy-Benzaldehyde	biospider
4-Hydroxybenzaldehyde, homopolymer	biospider
Benzaldehyde, 4-hydroxy-	biospider
Benzaldehyde, 4-hydroxy-, homopolymer	biospider
Benzaldehyde, p-hydroxy-	biospider
HBA	biospider
P-Hydroxy-benzaldehyde	HMDB
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-8900000000-4eff34096f6bd4f30d10	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9800000000-c8646d08ef8e23a3d49b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-8900000000-60621d4d9871b2d7587d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i0-1970000000-7ef151eab685361413a6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-1940000000-fa6b812457f26dce7720	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-2940000000-0bfc68ade3f25f6ba1f2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-2940000000-b50ed8954cb10b92a30b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-2930000000-671031e52722de3402ec	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-8900000000-4eff34096f6bd4f30d10	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9800000000-c8646d08ef8e23a3d49b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-8900000000-60621d4d9871b2d7587d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05i0-1970000000-7ef151eab685361413a6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-1940000000-fa6b812457f26dce7720	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-2940000000-0bfc68ade3f25f6ba1f2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-2940000000-b50ed8954cb10b92a30b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00b9-2930000000-671031e52722de3402ec	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-ea309e8826550692ddeb	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8900000000-781df730e85ee6b33891	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0900000000-99136b39c7ec11a7bbca	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-00di-0900000000-ab4c213ba9a645517aa3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9300000000-7a1d8d268b763ce71331	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-002g-9000000000-e9050639f16e3b6d7939	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-00di-0900000000-27effb3a35bdb0d72310	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-00di-1900000000-731f917249c17a761e0f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-00dj-5900000000-c46a92738e14de26b66c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-006t-9500000000-7f1f8c64931b0dc6f66f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0002-9100000000-39037b9523c5f3c7ed6c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0002-9000000000-06c809ed4b25327e8b09	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-002b-9000000000-b93cdaad48fe246028dd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-002b-9000000000-16e7fae11656d4e6cd8a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0fba-9000000000-96924ab5b95b0d4fb857	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-298ab6a83ac989405983	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-12ad1640340af91bc8e8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0036-9000000000-ddc48e682b255bd53c5e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-785058db9c1fbc1b5950	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-c22365c838c065b99ed8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0100-9300000000-491fc6287b2479ddc1a6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-298ab6a83ac989405983	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-12ad1640340af91bc8e8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0036-9000000000-ddc48e682b255bd53c5e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-785058db9c1fbc1b5950	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-c22365c838c065b99ed8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0100-9300000000-491fc6287b2479ddc1a6	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9500000000-2c1739a8a2bc288e4a5c	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

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.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound 4-Hydroxybenzaldehyde (FDB010504)

Structure for FDB010504 (4-Hydroxybenzaldehyde)