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

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Record Information
Version1.0
Created at2020-04-27 16:46:44 UTC
Updated at2021-01-04 18:49:09 UTC
CannabisDB IDCDB005698
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1,4-Dimethoxybenzene
Description1,4-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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
14-DimethoxybenzeneChEMBL, HMDB
1, 3-Bis(hydroxymethyl)-2-benzimidazolinoneHMDB
1,3-Bis(hydroxymethyl)-2-benzimidazolinoneHMDB
1,4-Dimethoxy benzeneHMDB
1,4-Dimethoxy-benzeneHMDB
1,4-DimethoxybenzolHMDB
4-MethoxyanisoleHMDB
4-Methoxyphenol, methyl etherHMDB
Dimethyl ether hydroquinoneHMDB
Dimethyl hydroquinoneHMDB
Dimethylether hydrochinonuHMDB
DimethylhydroquinoneHMDB
Dimethylhydroquinone etherHMDB
DimethylolbenzimidazolonHMDB
DMBHMDB
Hydroquinone dimethyl etherHMDB
Hydroquinone, dimethyl etherHMDB
Methyl P-methoxyphenyl etherHMDB
P-Dimethoxy-benzeneHMDB
P-DimethoxybenzeneHMDB
P-Methoxy-anisoleHMDB
P-MethoxyanisoleHMDB
Quinol dimethyl etherHMDB
Para-dimethoxybenzeneMeSH, HMDB
Chemical FormulaC8H10O2
Average Molecular Weight138.16
Monoisotopic Molecular Weight138.0681
IUPAC Name1,4-dimethoxybenzene
Traditional Name1,4-dimethoxybenzene
CAS Registry Number150-78-7
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 KeyOHBQPCCCRFSCAX-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point55 - 56 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP2.04Not Available
Predicted Properties
PropertyValueSource
logP2.05ALOGPS
logP1.66ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.98 m³·mol⁻¹ChemAxon
Polarizability14.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-3900000000-83320534feed23b07657Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-9800000000-f7ee9b9c0cbc026ac7d9Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-0079-0900000000-d37b2ca3e560908cc602Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-7900000000-0d29222a67c465237ce2Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-7900000000-0d29222a67c465237ce2Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-0079-5900000000-acbf1612453243f711e3Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-9400000000-1cbab0524dd620c92335Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-3900000000-83320534feed23b07657Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-9800000000-f7ee9b9c0cbc026ac7d9Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-0079-0900000000-d37b2ca3e560908cc602Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-7900000000-0d29222a67c465237ce2Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-7900000000-0d29222a67c465237ce2Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-0079-5900000000-acbf1612453243f711e3Spectrum
GC-MS1,4-Dimethoxybenzene , non-derivatized, GC-MS Spectrumsplash10-00dr-9400000000-1cbab0524dd620c92335Spectrum
Predicted GC-MS1,4-Dimethoxybenzene , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-3900000000-3b2e9d7e8452b0a3d8baSpectrum
Predicted GC-MS1,4-Dimethoxybenzene , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,4-Dimethoxybenzene , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-20aae7ad5b5ec6c7956f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-461cb2ee91a194ee4b3a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc9-8900000000-cd4aecf5573c330cb2d52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-64595b22b622b7640bca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-0a77422bf12a6c3ece0b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-237cdb6b19bd96847e4e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-2f7832bb660fbb1dff782021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-ddd925926a9c5068b4c72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wmi-9000000000-0f93a76ebcde785473672021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-08ef9d705ca98ce39abf2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-cbbf74f96a0823d0a9482021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f38e0a417b35f6456df32021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029671
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000855
KNApSAcK IDC00036386
Chemspider ID21105878
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,4-Dimethoxybenzene
METLIN IDNot Available
PubChem Compound9016
PDB IDNot Available
ChEBI ID1167379
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]