Cannabis Compound Database: Showing Compound Card for o-Dimethyl hydroquinone (CDB000648)

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Record Information

Version

1.0

Created at

2020-03-19 00:48:48 UTC

Updated at

2021-01-04 18:48:56 UTC

CannabisDB ID

CDB000648

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

o-Dimethyl hydroquinone

Description

1,2-Dimethoxybenzene, also known as veratrole, o-Dimethylhydroquinone or 2-Methoxyanisole 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. 1,2-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. It is the dimethyl ether derived from pyrocatechol. 1,2-Dimethoxybenzene exists as a clear, colorless liquid and is slightly soluble in water, but miscible in all organic solvents. 1,2-Dimethoxybenzene has a sweet, vanilla, creamy, and musty aroma. It is used as both a flavoring agent and a perfurming agent. 1,2-Dimethoxybenzene has been detected, but not quantified in, several different foods, such as corn, coffee, curry, rice, tea, milk and milk products, broccoli, and green vegetables. 1,2-Dimethoxybenzene is relatively electron-rich and thus readily undergoes electrophilic substitution, making it an ideal building block for the organic synthesis of other aromatic compounds. 1,2-Dimethoxybenzene also functions as an insect attractant for pollinating plants (PMID: 22937972 ). Dimethoxybenzenes are found in cannabis smoke. 1,2-Dimethoxybenzene is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-Dimethoxybenzol	ChEBI
2-Methoxyanisole	ChEBI
Catechol dimethyl ether	ChEBI
Methyl guaiacol	ChEBI
O,O-Dimethyl catechol	ChEBI
O-Dimethoxybenzene	ChEBI
Pyrocatechol dimethyl ether	ChEBI
Veratrole	MeSH
FEMA 3799	HMDB
Guaiacol methylether	HMDB
O-Dimethoxy-benzene	HMDB
Orthodimethoxybenzene	HMDB
Synthol	HMDB
Veratrol	HMDB
1,2-Dimethoxybenzene	MeSH

Chemical Formula

C₈H₁₀O₂

Average Molecular Weight

138.16

Monoisotopic Molecular Weight

138.0681

IUPAC Name

1,2-dimethoxybenzene

Traditional Name

veratrole

CAS Registry Number

91-16-7

SMILES

COC1=CC=CC=C1OC

InChI Identifier

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

InChI Key

ABDKAPXRBAPSQN-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

O-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

dimethoxybenzene (CHEBI:59114 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Poaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Laboratory chemical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	22.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	1.60	Not Available

Predicted Properties

Property	Value	Source
logP	2.1	ALOGPS
logP	1.66	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	-4.6	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	14.65 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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0f9j-9300000000-84232d2a7771f5297e19	2015-03-01	View Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000j-9500000000-ba3df3a0cec54fd4ddb1	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000i-9600000000-f768976db437187c3fe9	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-9ce5b11ff09d03512069	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000i-7900000000-074bcd0c663f55639243	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000j-9500000000-f6904476f7cfb2482f90	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-0f96-9100000000-82821a5bc5bbc4df87be	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000j-9500000000-ba3df3a0cec54fd4ddb1	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000i-9600000000-f768976db437187c3fe9	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-9ce5b11ff09d03512069	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000i-7900000000-074bcd0c663f55639243	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-000j-9500000000-f6904476f7cfb2482f90	Spectrum
GC-MS	o-Dimethyl hydroquinone, non-derivatized, GC-MS Spectrum	splash10-0f96-9100000000-82821a5bc5bbc4df87be	Spectrum
Predicted GC-MS	o-Dimethyl hydroquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-6900000000-3def7a8de562d9ad8c38	Spectrum
Predicted GC-MS	o-Dimethyl hydroquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-000i-0900000000-59a80da831843d5184e1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-000i-0900000000-d543225601eac501e480	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-0900000000-0dc8d9858fc1f6303e92	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-0900000000-2083d26506807f5733cd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-0900000000-da241afd8465683b4338	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0079-0900000000-6a74d1e3dd466db53877	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0079-0900000000-608cccb6ae052653a61b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-00dr-0900000000-4dd50241a6ad9dc07120	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-00dr-0900000000-2df36af936932591c82d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-00dr-0900000000-0c8975f2c2c954725d97	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-00di-1900000000-408b3a6fa1dcb4b736b1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0ab9-3900000000-37537f5395c7cdd9d04e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0a4i-6900000000-b34376ed4e790654e616	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-0a59-9400000000-4b20048c8c78431c945e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-001i-9100000000-75adf0e079ec008653ec	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-0f89-9000000000-f5043fce7ffa5ce956c7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-00di-0900000000-66be3b4be4fff2fa073b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-004i-9000000000-a6d296f4cff997d26f26	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-0a4i-0900000000-551ac0f723bcc2798d25	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-fca0b605e8d5224b20a6	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-065ed98981a51fc3722f	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9300000000-ee666f72073d7c63af1b	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-6dd2938f60d4205e97a6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-1c3155acdb826f8cb385	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ki7-9200000000-9b9c41d6b2a64125ccf0	2016-08-03	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	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

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

HMDB0032139

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008865

KNApSAcK ID

C00056272

Chemspider ID

13861009

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Veratrole

METLIN ID

Not Available

PubChem Compound

7043

PDB ID

Not Available

ChEBI ID

59114

References

General References

Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
Gupta AK, Akhtar TA, Widmer A, Pichersky E, Schiestl FP: Identification of white campion (Silene latifolia) guaiacol O-methyltransferase involved in the biosynthesis of veratrole, a key volatile for pollinator attraction. BMC Plant Biol. 2012 Aug 31;12:158. doi: 10.1186/1471-2229-12-158. [PubMed:22937972 ]

Showing Compound Card for o-Dimethyl hydroquinone (CDB000648)

Structure for CDB000648 (o-Dimethyl hydroquinone)