Basic information
- Standard SMILES
COc1cccc(OC)c1O- InChIKey
KLIDCXVFHGNTTM-UHFFFAOYSA-N- Molecular formula
- C8H10O3
- Average molar mass
- 154.16 g/mol
- Monoisotopic mass
- 154.06299418
Overview
2,6-dimethoxyphenol is a member of the class of phenols that is phenol substituted by methoxy groups at positions 2 and 6. It has a role as a plant metabolite. It is a member of phenols and a dimethoxybenzene.
Names & identifiers
- Preferred name
- 2,6-Dimethoxyphenol
- IUPAC
- 2,6-dimethoxyphenol
- English name
- 2,6-Dimethoxyphenol
- Molecular formula
- C8H10O3
- Molecular weight
- 154.16
Names & synonyms
2,6-DIMETHOXYPHENOL91-10-1SyringolPyrogallol 1,3-dimethyl etherPhenol, 2,6-dimethoxy-1,3-Dimethoxy-2-hydroxybenzene2-Hydroxy-1,3-dimethoxybenzene1,3-Dimethyl pyrogallate1,3-Di-o-methylpyrogallolPyrogallol dimethyletherFEMA No. 3137DTXSID2052607
Show more names
MCPDimethoxyphenol2,6-Dimethoxyphenol (syringol)2,6-DimethoxyphenylNatural 2,6-DimethoxyphenolAHUS2MIC10
4UQT464H8KCHEBI:955DTXCID0031180RefChem:83270202-041-1Aldrich2,6-Dwumetoksyfenol2,6-dimethoxy phenol
Database identifiers
- CAS
91-10-1- PubChem CID
- 7041
- DTXSID
DTXSID2052607- ChEMBL
CHEMBL109652- ChEBI
CHEBI:955- UNII
- 4UQT464H8K
- EC Number
- 202-041-1
- Nikkaji
- J27.321J
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 38.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 104
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Other Aromatic Compounds
FragrancesFragrance Ingredient (2,6-Dimethoxyphenol) -> IFRA transparency List
LogP
1.15
1.15
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
17.2 mg/mL at 13 °C
slightly soluble in water; soluble in oils
moderately soluble (in ethanol)
Boiling Point
260.00 to 261.00 °C. @ 760.00 mm Hg
261-262 °C
Melting Point55 - 56 °C
Physical Description
Light brown solidified mass or fragments; [Aldrich MSDS]
Solid
White or colourless crystals, woody medicinal rather dry odour
Physicochemical properties
- Melting point
- 50 · 50-57 °C(lit.)
- Boiling point
- 261 °C · 261 °C(lit.)
- Density
- 1.169 · 1.1690 (rough estimate)
- refractive index
- 1.4745 · 1.4745 (estimate)
- FEMA
- 3137 · 3137 | 2,6-DIMETHOXYPHENOL
- FLAVIS Number
- 4.036 · 04.036 | 2,6-Dimethoxyphenol
- Flash point
- 230 °F · >230 °F
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Crystalline Powder, Crystals, or Crystalline Solid
- pka
- 9.97 · 9.97±0.10(Predicted)
- color
- Off-white or gray to brown
- Odor
- 1 % · at 1.00 % in dipropylene glycol. smoky phenolic balsamic bacon powdery woody
- Odor Type
- smoky
- biological source
- synthetic
- Water Solubility
- 2 g/100 · 2 g/100 mL (13 ºC)
- JECFA Number
- 721 · 721
- BRN
- 1526871 · 1526871
- Henry's Law Constant
- 3.7 · 3.7×101 mol/(m3Pa) at 25℃, Sagebiel et al. (1992)
- InChI
- 1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3
- InChIKey
- KLIDCXVFHGNTTM-UHFFFAOYSA-N
- SMILES
- COc1cccc(OC)c1O
- LogP
- 0.77 · 0.77
- CAS DataBase Reference
- 91 · 91-10-1(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 2 · 2,6-DIMETHOXYPHENOL
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 UQT464H8K · 4UQT464H8K
- NIST Chemistry Reference
- 2 · Phenol, 2,6-dimethoxy-(91-10-1)
- EPA Substance Registry System
- 2 · Phenol, 2,6-dimethoxy- (91-10-1)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 301 · P301+P312+P330-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-36-37/39
- RIDADR
- 2811 · UN 2811 6.1/PG 1
- WGK Germany
- 3 · 3
- RTECS
- 900000 · SL0900000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29095090 · 29095090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1711) of reports.
Warning
H302 (> 99.9%): 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 1711 reports by companies from 12 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Phenol, 2,6-dimethoxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 27-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24958
Phenol, 2,6-dimethoxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes somnolence and dyspnea in intravenous lethal-dose study of cats; Causes general anesthesia in oral lethal-dose study of rats; Causes weight loss in 36-day oral studies of rats; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; Harmful by ingestion and skin absorption; [Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (> 99.9%)
Toxicology
Adverse EffectsNeurotoxin - Acute solvent syndrome
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SL0900000
- ridadr
- UN 2811 6.1/PG 1
- hs_code
- 29095090
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P301+P312+P330-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as flavoring agent or adjuvant; [FDA]
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationPhenol, 2,6-dimethoxy-: ACTIVE
Applications
OccurrenceReported found in beechwood tar creosote, onion, garlic, leek, chive, nira (Allium tuberosum Rotti), nobira (Allium grayi Regal) and caucus (Allium victoralis L.)
Uses2,6-Dimethoxyphenol has been used as a metabolite of lignin depolymerisation.It is also used as flavoring agent or adjuvant.It is reported to be the single most important flavor chemical in smoke flavors. It is used in smoke flavors, whisky, rum, tea, spice, savory, seafood, meat, liquorices, coffee, and nut flavors.
General Description2,6-Dimethoxyphenol has been identified as one of the volatile flavor constituents in shoyu (soy sauce), wine and wood smoke.
Preparation methods
Preparation2,6-Dimethoxyphenol is prepared by reacting pyrogallol with methyl iodide in alkaline aqueous medium; by demethylation of pyrogallol trimethyl ether in aqueous alkali or in alcohol.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 2,6-dimethoxyphenol is a member of the class of phenols that is phenol substituted by methoxy groups at positions 2 and 6. It has a role as a plant metabolite. It is a member of phenols and a dimethoxybenzene.
Related reactions
43 records
Linked notes
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