Veratrole
Basic information
- CAS
91-16-7- Standard SMILES
COc1ccccc1OC- InChIKey
ABDKAPXRBAPSQN-UHFFFAOYSA-N- Molecular formula
- C8H10O2
- Average molar mass
- 138.16 g/mol
- Monoisotopic mass
- 138.06807956
Overview
Veratrole is a dimethoxybenzene with the methoxy groups at ortho-positions. It has a role as a plant metabolite.
Names & identifiers
- Preferred name
- Veratrole
- IUPAC
- 1,2-dimethoxybenzene
- English name
- 1,2-Dimethoxybenzene
- Molecular formula
- C8H10O2
- Molecular weight
- 138.16
Names & synonyms
1,2-DimethoxybenzeneVeratrole91-16-7VeratrolO-DIMETHOXYBENZENEPyrocatechol dimethyl etherCatechol dimethyl ether2-MethoxyanisoleBenzene, 1,2-dimethoxy-2-DimethoxybenzolO,O-Dimethyl catecholSynthol
Show more names
ODMBVeretroleFEMA 37991,2-DimethoxybenzolGUAIACOL METHYL ETHER
BrenzkatechindimethyletherFEMA No. 3799Dimethylether pyrokatechinuDTXSID704706561WJZ2Q41INSC-16934DTXCID5027065CHEBI:59114
Database identifiers
- CAS
91-16-7- PubChem CID
- 7043
- DTXSID
DTXSID7047065- ChEMBL
CHEMBL1668603- ChEBI
CHEBI:59114- UNII
- 61WJZ2Q41I
- EC Number
- 202-045-3
- Nikkaji
- J4.334F
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 18.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 81.3
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Ethers, Other
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (1,2-Dimethoxybenzene) -> IFRA transparency List
LogP
1.60
1.79
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
1.082-1.086
1.081 @25 °C
Flavoring AgentsEU Flavoring substances
Solubility
Insoluble in water
soluble (in ethanol)
Boiling Point
206.00 °C. @ 760.00 mm Hg
206-207 °C
206 °C @760 [mm Hg]
Melting Point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1781 reports by companies from 5 notifications to the ECHA C&L Inventory.
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory Information
Chemical: Benzene, 1,2-dimethoxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Benzene, 1,2-dimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,2-dimethoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: Veratrole (EC: 202-045-3)
Veratrole: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] An irritant; Harmful by ingestion; [Alfa Aesar MSDS] See Anisole.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity (Oral) - Category 4
Safety & protection
Protective Action Criteria (PAC)
2.7 [mg/m3]
29 [mg/m3]
180 [mg/m3]
Safety data
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
U.S. Production2023: 50,000 - <250,000 lb
Industry UsesIntermediate
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Benzene, 1,2-dimethoxy-: ACTIVE
Applications
Description1, 2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula C6H4(OCH3)2. It is a colorless liquid with a pleasant odor and slight solubility in water. It is the dimethyl ether derived from pyrocatechol, too. 1, 2-Dimethoxybenzene is naturally occurring. Its biosynthesis entails the methylation of guaiacol by guaiacol O-methyltransferase.1, 2-Dimethoxybenzene is an insect attractant. Guaiacol O-methyltransferase gene is first scent gene discovered so far in any plant species.
Uses1, 2-Dimethoxybenzene is a building block for the organic synthesis of other aromatic compounds. Veratrole is relatively electron-rich and thus readily undergoes electrophilic substitution. An example of the use of veratrole is in the synthesis of Domipizone. Veratrole can easily be brominated with NBS to give 4-bromoveratrole.
OccurrenceReported present in asparagus (raw and cooked), bonito (dried), broccoli (cooked), cauliflower (cooked), cognac, endive, grape, Gruyere de Comte cheese, guava, leek (raw and heated), olive, peas, rhubarb, rice bran and vanilla extract.
Related reactions
295 records
Compound notes
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