Cannabis Compound Database: Showing Compound Card for 1,4-Dimethoxybenzene (CDB005698)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References XML

Show more...Show more...Show more...

Record Information

Version

1.0

Created at

2020-04-27 16:46:44 UTC

Updated at

2021-01-04 18:49:09 UTC

CannabisDB ID

CDB005698

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

1,4-Dimethoxybenzene

Description

1,4-Dimethoxybenzene, also known as dimethyl hydroquinone or p-methoxy-anisole, is one of three structural isomers of dimethoxybenzene wherein two methoxy groups are substituted at three positions (the 1,2-, 1,3- and 1,4- positions) of the benzene ring. 1,4-Dimethoxybenzene belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. 1,4-Dimethoxybenzene exists as a white solid and is largely insoluble in water. 1,4-Dimethoxybenzene has a sweet, green and fennel-like aroma and an anise, powdery, earthy, fatty taste. It is approved for use as a flavoring ingredient and as a perfuming agent. 1,4-Dimethoxybenzene is mainly used in perfumes and soaps. It is also used as an intermediate in synthesis of organic compounds, including pharmaceuticals and as a developer in black and white film. 1,4-Dimethoxybenzene has been used as a base in synthesizing catecholamines and phenethylamines. Industrially, 1,4-Dimethoxybenzene is produced by the methylation of hydroquinone using dimethylsulfate and an alkali. 1,4-Dimethoxybenzene also occurs naturally and is found in willow (Salix), tea, coffee, papaya, hyacinth, zucchini (Cucurbita pepo) and in higher concentrations within peppermints. 1,4-Dimethoxybenzene appears to have pheromone-like activity as a floral volatile and attracts bees as it has a powerful response in their antenna (PMID: 16258713 , 30481663 ). 1,4-Dimethoxybenzene has also been identified as a breakdown product of acetaminophen in soil (PMID: 24316789 ). Dimethoxybenzenes are found in cannabis smoke. 1,4-Dimethoxybenzene is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
14-Dimethoxybenzene	ChEMBL, HMDB
1, 3-Bis(hydroxymethyl)-2-benzimidazolinone	HMDB
1,3-Bis(hydroxymethyl)-2-benzimidazolinone	HMDB
1,4-Dimethoxy benzene	HMDB
1,4-Dimethoxy-benzene	HMDB
1,4-Dimethoxybenzol	HMDB
4-Methoxyanisole	HMDB
4-Methoxyphenol, methyl ether	HMDB
Dimethyl ether hydroquinone	HMDB
Dimethyl hydroquinone	HMDB
Dimethylether hydrochinonu	HMDB
Dimethylhydroquinone	HMDB
Dimethylhydroquinone ether	HMDB
Dimethylolbenzimidazolon	HMDB
DMB	HMDB
Hydroquinone dimethyl ether	HMDB
Hydroquinone, dimethyl ether	HMDB
Methyl P-methoxyphenyl ether	HMDB
P-Dimethoxy-benzene	HMDB
P-Dimethoxybenzene	HMDB
P-Methoxy-anisole	HMDB
P-Methoxyanisole	HMDB
Quinol dimethyl ether	HMDB
Para-dimethoxybenzene	MeSH, HMDB

Chemical Formula

C₈H₁₀O₂

Average Molecular Weight

138.16

Monoisotopic Molecular Weight

138.0681

IUPAC Name

1,4-dimethoxybenzene

Traditional Name

1,4-dimethoxybenzene

CAS Registry Number

150-78-7

SMILES

COC1=CC=C(OC)C=C1

InChI Identifier

InChI=1S/C8H10O2/c1-9-7-3-5-8(10-2)6-4-7/h3-6H,1-2H3

InChI Key

OHBQPCCCRFSCAX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

P-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Phenol ether
Anisole
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	55 - 56 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	2.04	Not Available

Predicted Properties

Property	Value	Source
logP	2.05	ALOGPS
logP	1.66	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	38.98 m³·mol⁻¹	ChemAxon
Polarizability	14.83 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-3900000000-83320534feed23b07657	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-9800000000-f7ee9b9c0cbc026ac7d9	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-0079-0900000000-d37b2ca3e560908cc602	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-7900000000-0d29222a67c465237ce2	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-7900000000-0d29222a67c465237ce2	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-0079-5900000000-acbf1612453243f711e3	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-9400000000-1cbab0524dd620c92335	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-3900000000-83320534feed23b07657	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-9800000000-f7ee9b9c0cbc026ac7d9	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-0079-0900000000-d37b2ca3e560908cc602	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-7900000000-0d29222a67c465237ce2	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-7900000000-0d29222a67c465237ce2	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-0079-5900000000-acbf1612453243f711e3	Spectrum
GC-MS	1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrum	splash10-00dr-9400000000-1cbab0524dd620c92335	Spectrum
Predicted GC-MS	1,4-Dimethoxybenzene , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-3900000000-3b2e9d7e8452b0a3d8ba	Spectrum
Predicted GC-MS	1,4-Dimethoxybenzene , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,4-Dimethoxybenzene , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-20aae7ad5b5ec6c7956f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-461cb2ee91a194ee4b3a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc9-8900000000-cd4aecf5573c330cb2d5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-64595b22b622b7640bca	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-0a77422bf12a6c3ece0b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9700000000-237cdb6b19bd96847e4e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-2f7832bb660fbb1dff78	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2900000000-ddd925926a9c5068b4c7	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0wmi-9000000000-0f93a76ebcde78547367	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-08ef9d705ca98ce39abf	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2900000000-cbbf74f96a0823d0a948	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-f38e0a417b35f6456df3	2021-09-25	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

Not Available

External Links

HMDB ID

HMDB0029671

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000855

KNApSAcK ID

C00036386

Chemspider ID

21105878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

1,4-Dimethoxybenzene

METLIN ID

Not Available

PubChem Compound

9016

PDB ID

Not Available

ChEBI ID

1167379

References

General References

Dotterl S, Fussel U, Jurgens A, Aas G: 1,4-Dimethoxybenzene, a floral scent compound in willows that attracts an oligolectic bee. J Chem Ecol. 2005 Dec;31(12):2993-8. doi: 10.1007/s10886-005-9152-y. Epub 2005 Nov 4. [PubMed:16258713 ]
Zito P, Rosselli S, Bruno M, Maggio A, Sajeva M: Floral scent in Iris planifolia (Iridaceae) suggests food reward. Phytochemistry. 2019 Feb;158:86-90. doi: 10.1016/j.phytochem.2018.11.011. Epub 2018 Nov 24. [PubMed:30481663 ]
Li J, Ye Q, Gan J: Degradation and transformation products of acetaminophen in soil. Water Res. 2014 Feb 1;49:44-52. doi: 10.1016/j.watres.2013.11.008. Epub 2013 Nov 20. [PubMed:24316789 ]

Showing Compound Card for 1,4-Dimethoxybenzene (CDB005698)

Structure for CDB005698 (1,4-Dimethoxybenzene )