Showing Compound 4-Hydroxy-3,5-dimethoxybenzaldehyde (FDB000822)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:43 UTC

Update date

2019-11-26 02:55:28 UTC

Primary ID

FDB000822

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Hydroxy-3,5-dimethoxybenzaldehyde

Description

4-hydroxy-3,5-dimethoxybenzaldehyde, also known as sinapaldehyde or 2,6-dimethoxy-4-formylphenol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 4-hydroxy-3,5-dimethoxybenzaldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-hydroxy-3,5-dimethoxybenzaldehyde is a mild, sweet, and plastic tasting compound and can be found in a number of food items such as whisky, common grape, garden tomato (variety), and coriander, which makes 4-hydroxy-3,5-dimethoxybenzaldehyde a potential biomarker for the consumption of these food products. 4-hydroxy-3,5-dimethoxybenzaldehyde may be a unique S.cerevisiae (yeast) metabolite. Because it contains many functional groups, it can be classified in many ways - aromatic, aldehyde, phenol. It is a colorless solid (impure samples appear yellowish) that is soluble in alcohol and polar organic solvents. Its refractive index is 1.53 .

CAS Number

134-96-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2,6-Dimethoxy-4-formylphenol	MeSH
3,5-Dimethoxy-4-hydroxy-benzaldehyde	PhytoBank
3,5-Dimethoxy-4-Hydroxy-Benzaldehyde	biospider
3,5-Dimethoxy-4-hydroxybenzaldehyde	MeSH
3,5-DIMETHOXY-4-HYDROXYBENZALDEHYDE, PURE	biospider
3,5-Dimethoxy-4-hydroxybenzene carbonal	biospider
4-Formyl-2,6-dimethoxyphenol	PhytoBank
4-Formylsyringol	PhytoBank
4-Hydroksy-3,5-dwumetoksybenzaldehyd	biospider
4-Hydroxy-3,5-dimethoxybenzaldehyde	PhytoBank

Showing 1 to 10 of 25 entries

Predicted Properties

Property	Value	Source
Water Solubility	3.68 g/L	ALOGPS
logP	1.33	ALOGPS
logP	1.07	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	7.24	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.55 m³·mol⁻¹	ChemAxon
Polarizability	17.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H10O4

IUPAC name

4-hydroxy-3,5-dimethoxybenzaldehyde

InChI Identifier

InChI=1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3

InChI Key

KCDXJAYRVLXPFO-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC(C=O)=CC(OC)=C1O

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

Classification

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Hydroxybenzaldehyde
Anisole
Benzaldehyde
Benzoyl
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Aryl-aldehyde
Monocyclic benzene moiety
Ether
Organooxygen compound
Aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dimethoxybenzene (CHEBI:67380 )
hydroxybenzaldehyde (CHEBI:67380 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp14 192-193°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 59.34%; H 5.53%; O 35.13%	DFC
Melting Point	Mp 113-114°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-5900000000-6cbbbdbec8f6bba463d5	2015-03-01	View Spectrum
Predicted GC-MS	4-Hydroxy-3,5-dimethoxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ue9-0900000000-ef96b9e519092161a3cb	Spectrum
Predicted GC-MS	4-Hydroxy-3,5-dimethoxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxy-3,5-dimethoxybenzaldehyde, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Hydroxy-3,5-dimethoxybenzaldehyde, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-9100000000-5b6ba3c42dcd3af29af0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-002b-9500000000-59dc9fbf56278b4fa3d7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00or-9000000000-7fdf6c97fc44ba928757	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-05gi-0900000000-44ca2aac27277cc862f5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-002b-9500000000-648b4cea88c99f600180	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-05gi-0900000000-ec8dfff58a288a3a2202	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-9100000000-54826f5ed4bf4c650678	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00or-9000000000-03822b23e64682ed8879	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-888409d99d78544d7bda	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-9a08dd0b4c0aa032b821	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0hhi-3900000000-9de8232d167c5c3dc77e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-9ff54d007d617002d730	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-5756b0978ed9c9206dfc	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0671-5900000000-61166ea22e1f8c56bc12	2016-08-04	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

8655

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

722

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

BJH89-J:BJH96-J

EAFUS ID

1742

Dr. Duke ID

SYRINGALDEHYDE

BIGG ID

Not Available

KNApSAcK ID

C00007558

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1026801

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

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Food	Content Range	Average	Reference

Coconut	Expected but not quantified	Not Available	DUKE
Common grape	Expected but not quantified	Not Available	DUKE
Common walnut	0.87300 - 26.25000 mg/100 g	9.341 mg/100 g	PHENOL EXPLORER, DUKE
Coriander	Expected but not quantified	Not Available	DUKE
Corn	Expected but not quantified	Not Available	DUKE
Garden tomato (var.)	Expected but not quantified	Not Available	DUKE
Grape wine	0.000 - 0.668 mg/100 g	0.33387 mg/100 g	PHENOL EXPLORER
Rum	0.04300 - 0.04300 mg/100 g	0.04300 mg/100 g	PHENOL EXPLORER
Spirit	0.09711 - 0.09711 mg/100 g	0.09711 mg/100 g	PHENOL EXPLORER
Vinegar	0.07665 - 0.07665 mg/100 g	0.07665 mg/100 g	PHENOL EXPLORER

Showing 1 to 10 of 11 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti edemic			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	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
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE

Showing 1 to 4 of 4 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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