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91-10-1

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91-10-1 Usage

Chemical Properties

2,6-Dimethoxyphenol is an off-white or grey to brown crystalline powder that has a woody, medicinal, rather dry odor.

Occurrence

Reported found in beechwood tar creosote, onion, garlic, leek, chive, nira (Allium tuberosum Rotti), nobira (Allium grayi Regal) and caucus (Allium victoralis L.)

Uses

2,6-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.

Definition

ChEBI: 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.

Preparation

2,6-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.

Aroma threshold values

Detection: 400 ppb to 1.85 ppm

Taste threshold values

Taste characteristics at 60 ppm: sweet, medicinal, creamy, meaty, vanilla, spice.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 4444, 1979 DOI: 10.1021/jo01338a043Tetrahedron Letters, 34, p. 7667, 1993 DOI: 10.1016/S0040-4039(00)61534-4

General Description

2,6-Dimethoxyphenol has been identified as one of the volatile flavor constituents in shoyu (soy sauce), wine and wood smoke.

Purification Methods

Purify the phenol by zone melting or sublimation in a vacuum. [Beilstein 6 IV 7329.]

Check Digit Verification of cas no

The CAS Registry Mumber 91-10-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 91-10:
(4*9)+(3*1)+(2*1)+(1*0)=41
41 % 10 = 1
So 91-10-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3

91-10-1 Well-known Company Product Price

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  • Alfa Aesar

  • (B24253)  2,6-Dimethoxyphenol, 99%   

  • 91-10-1

  • 25g

  • 311.0CNY

  • Detail
  • Alfa Aesar

  • (B24253)  2,6-Dimethoxyphenol, 99%   

  • 91-10-1

  • 100g

  • 1172.0CNY

  • Detail
  • Sigma-Aldrich

  • (53877)  2,6-Dimethoxyphenol  analytical standard

  • 91-10-1

  • 53877-100MG

  • 1,628.64CNY

  • Detail

91-10-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,6-dimethoxyphenol

1.2 Other means of identification

Product number -
Other names Phenol, 2,6-dimethoxy-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:91-10-1 SDS

91-10-1Relevant articles and documents

Wildenhain,Henseke

, p. 479 (1969)

One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles

Guo, Tao,He, Jianghua,Liu, Tianwei,Zhang, Yuetao

supporting information, (2022/02/07)

It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.

Eco-friendly preparation of ultrathin biomass-derived Ni3S2-doped carbon nanosheets for selective hydrogenolysis of lignin model compounds in the absence of hydrogen

Chen, Changzhou,Jiang, Jianchun,Li, Jing,Liu, Peng,Wu, Dichao,Xia, Haihong,Zhou, Minghao

, p. 3090 - 3103 (2021/05/07)

Lignin is an abundant source of aromatics, and the depolymerization of lignin provides significant potential for producing high-value chemicals. Selective hydrogenolysis of the C-O ether bond in lignin is an important strategy for the production of fuels and chemical feedstocks. In our study, catalytic hydrogenolysis of lignin model compounds (β-O-4, α-O-4 and 4-O-5 model compounds) over Ni3S2-CS catalysts was investigated. Hence, an array of 2D carbon nanostructure Ni3S2-CSs-X-Yderived catalysts were produced using different compositions at different temperatures (X= 0 mg, 0.2 mg, 0.4 mg, 0.6 mg, and 0.8 mg; Y = 600 °C, 700 °C, 800 °C, and 900 °C) were prepared and applied for hydrogenolysis of lignin model compounds and depolymerization of alkaline lignin. The highest conversion of lignin model compounds (β-O-4 model compound) was up to 100% and the yield of the obtained corresponding ethylbenzene and phenol could achieve 92% and 86%, respectively, over the optimal Ni3S2-CSs-0.4-700 catalyst in iPrOH at 260 °C without external H2. The 2D carbon nanostructure catalysts performed a good dispersion on the surface of the carbon nanosheets, which facilitated the cleavage of the lignin ether bonds. The physicochemical characterization studies were carried out by means of XRD, SEM, TEM, H2-TPR, NH3-TPD, Raman and XPS analyses. Based on the optimal reaction conditions (260 °C, 4 h, 2.0 MPa N2), various model compounds (β-O-4, α-O-4 and 4-O-5 model compounds) could also be effectively hydrotreated to produce the corresponding aromatic products. Furthermore, the optimal Ni3S2-CSs-0.4-700 catalyst could be carried out in the next five consecutive cycle experiments with a slight decrease in the transformation of lignin model compounds.

Application of tungsten oxide supported monatomic catalyst in preparation of aromatic compound by hydrogenolysis of lignin

-

Paragraph 0044-0051, (2021/05/22)

The invention provides application of a tungsten oxide supported monatomic catalyst in preparation of aromatic compounds by hydrogenolysis of lignin. According to the method, various beta-O-4 model molecules, organic lignin, lignosulfonate and alkali lignin are taken as raw materials, and high-selectivity cracking of aryl ether bonds is realized in a hydrogen atmosphere at the temperature of 150-240 DEG C and the pressure of 0.7-3.0 MPa to obtain the aromatic compound. Compared with the prior art, the method has the advantages that when renewable natural biomass is used as the raw material and different lignin is used as the raw material for conversion, the highest yield of the aromatic bio-oil is 72%. Raw materials are cheap and wide in source; inorganic acid and alkali are not needed, and generation of a large amount of alkali liquor in traditional lignin catalysis is avoided; the method has the characteristics of cheap tungsten-based catalyst, green reaction process, atom economy and the like, and also has the characteristics of mild reaction conditions, high activity and selectivity, environment-friendly reaction process and the like.

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