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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:05 UTC

Update Date

2023-02-21 17:21:39 UTC

HMDB ID

HMDB0032139

Secondary Accession Numbers

HMDB32139

Metabolite Identification

Common Name

1,2-Dimethoxybenzene

Description

1,2-Dimethoxybenzene, commonly known as veratrole, is a chemical compound with the formula C6H4(OCH3)2. It is the dimethyl ether derived from pyrocatechol. Veratrole is slightly soluble in water, but miscible in all organic solvents. It is a building block for the organic synthesis of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes electrophilic substitution. 1,2-Dimethoxybenzene is found in corn. 1,2-Dimethoxybenzene is a food additive listed in the EAFUS food Additive Database (Jan 2001). 1,2-Dimethoxybenzene is found in raw and cooked foods, e.g. cheeses, grapes and asparagus.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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

138.1638

Monoisotopic Molecular Weight

138.068079564

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

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032139)
Cytoplasm (HMDB: HMDB0032139)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032139)

Source

Endogenous

Endogenous (HMDB: HMDB0032139)

Plant

Plant (HMDB: HMDB0032139)
Poaceae (HMDB: HMDB0032139)

Animal

Animal (HMDB: HMDB0032139)

Exogenous

Food

Food (HMDB: HMDB0032139)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Cabbage

Broccoli (FooDB: FOOD00034)
Cauliflower (FooDB: FOOD00031)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Tea

Fruit

Fruits (FooDB: FOOD00871)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Exogenous (HMDB: HMDB0032139)

Process

Not Available

Role

Industrial application

Manufacturing industry

Laboratory chemical

Laboratory chemical (HMDB: HMDB0032139)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	22.5 °C	Not Available
Boiling Point	206.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3666 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.60	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.42 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.72	31661259
DarkChem	[M-H]-	127.543	31661259
DeepCCS	[M+H]+	125.061	30932474
DeepCCS	[M-H]-	121.854	30932474
DeepCCS	[M-2H]-	158.752	30932474
DeepCCS	[M+Na]+	133.707	30932474
AllCCS	[M+H]+	128.0	32859911
AllCCS	[M+H-H2O]+	123.3	32859911
AllCCS	[M+NH4]+	132.4	32859911
AllCCS	[M+Na]+	133.7	32859911
AllCCS	[M-H]-	126.2	32859911
AllCCS	[M+Na-2H]-	128.0	32859911
AllCCS	[M+HCOO]-	130.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Dimethoxybenzene	COC1=CC=CC=C1OC	1716.5	Standard polar	33892256
1,2-Dimethoxybenzene	COC1=CC=CC=C1OC	1103.2	Standard non polar	33892256
1,2-Dimethoxybenzene	COC1=CC=CC=C1OC	1147.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-000j-9500000000-ba3df3a0cec54fd4ddb1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-000i-9600000000-f768976db437187c3fe9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene CI-B (Non-derivatized)	splash10-000i-0900000000-9ce5b11ff09d03512069	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-000i-7900000000-074bcd0c663f55639243	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-000j-9500000000-f6904476f7cfb2482f90	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-0f96-9100000000-82821a5bc5bbc4df87be	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-000j-9500000000-ba3df3a0cec54fd4ddb1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-000i-9600000000-f768976db437187c3fe9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene CI-B (Non-derivatized)	splash10-000i-0900000000-9ce5b11ff09d03512069	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-000i-7900000000-074bcd0c663f55639243	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-000j-9500000000-f6904476f7cfb2482f90	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dimethoxybenzene EI-B (Non-derivatized)	splash10-0f96-9100000000-82821a5bc5bbc4df87be	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dimethoxybenzene GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-6900000000-3def7a8de562d9ad8c38	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dimethoxybenzene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f9j-9300000000-84232d2a7771f5297e19	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 0V, positive-QTOF	splash10-000i-0900000000-59a80da831843d5184e1	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 0V, positive-QTOF	splash10-000i-0900000000-d543225601eac501e480	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 1V, positive-QTOF	splash10-000i-0900000000-0dc8d9858fc1f6303e92	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 1V, positive-QTOF	splash10-000i-0900000000-2083d26506807f5733cd	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 1V, positive-QTOF	splash10-000i-0900000000-da241afd8465683b4338	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 2V, positive-QTOF	splash10-0079-0900000000-6a74d1e3dd466db53877	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 2V, positive-QTOF	splash10-0079-0900000000-608cccb6ae052653a61b	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 3V, positive-QTOF	splash10-00dr-0900000000-4dd50241a6ad9dc07120	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 3V, positive-QTOF	splash10-00dr-0900000000-2df36af936932591c82d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 3V, positive-QTOF	splash10-00dr-0900000000-0c8975f2c2c954725d97	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 4V, positive-QTOF	splash10-00di-1900000000-408b3a6fa1dcb4b736b1	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 5V, positive-QTOF	splash10-0ab9-3900000000-37537f5395c7cdd9d04e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 6V, positive-QTOF	splash10-0a4i-6900000000-b34376ed4e790654e616	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 8V, positive-QTOF	splash10-0a59-9400000000-4b20048c8c78431c945e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 9V, positive-QTOF	splash10-001i-9100000000-75adf0e079ec008653ec	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene Orbitrap 12V, positive-QTOF	splash10-0f89-9000000000-f5043fce7ffa5ce956c7	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene n/a 9V, positive-QTOF	splash10-00di-0900000000-66be3b4be4fff2fa073b	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene n/a 9V, positive-QTOF	splash10-004i-9000000000-a6d296f4cff997d26f26	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2-Dimethoxybenzene n/a 9V, positive-QTOF	splash10-0a4i-0900000000-551ac0f723bcc2798d25	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dimethoxybenzene 10V, Positive-QTOF	splash10-000i-0900000000-fca0b605e8d5224b20a6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dimethoxybenzene 20V, Positive-QTOF	splash10-000i-0900000000-065ed98981a51fc3722f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dimethoxybenzene 40V, Positive-QTOF	splash10-0udi-9300000000-ee666f72073d7c63af1b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dimethoxybenzene 10V, Negative-QTOF	splash10-000i-0900000000-6dd2938f60d4205e97a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dimethoxybenzene 20V, Negative-QTOF	splash10-000i-0900000000-1c3155acdb826f8cb385	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dimethoxybenzene 40V, Negative-QTOF	splash10-0ki7-9200000000-9b9c41d6b2a64125ccf0	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1040471

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ding Q, Jia G, Lown JW: Synthesis and antitumor cytotoxicity evaluation of pyrido[4,3,2-de]quinolines and isoquinolino[6,5,4,3-cde]quinolines. Anticancer Drug Des. 2000 Apr;15(2):99-108. [PubMed:10901297 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 1,2-Dimethoxybenzene (HMDB0032139)

MOL for HMDB0032139 (1,2-Dimethoxybenzene)

3D MOL for HMDB0032139 (1,2-Dimethoxybenzene)

3D SDF for HMDB0032139 (1,2-Dimethoxybenzene)

3D-SDF for HMDB0032139 (1,2-Dimethoxybenzene)

PDB for HMDB0032139 (1,2-Dimethoxybenzene)

3D PDB for HMDB0032139 (1,2-Dimethoxybenzene)

SMILES for HMDB0032139 (1,2-Dimethoxybenzene)

INCHI for HMDB0032139 (1,2-Dimethoxybenzene)

Structure for HMDB0032139 (1,2-Dimethoxybenzene)

3D Structure for HMDB0032139 (1,2-Dimethoxybenzene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra