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4-methoxy-3-methylphenol, also known as guaiacol, is an aromatic organic compound characterized by the presence of a methoxy group (O-CH3) and a methyl group (CH3) attached to a benzene ring. It is widely recognized for its distinctive smoky, medicinal odor, typically associated with wood smoke. 4-methoxy-3-methyl-phenol has a broad spectrum of applications across various industries, including chemical, pharmaceutical, and food sectors, due to its unique properties and potential health benefits.

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  • 14786-82-4 Structure
  • Basic information

    1. Product Name: 4-methoxy-3-methyl-phenol
    2. Synonyms: 4-methoxy-3-methyl-phenol;Phenol, 4-Methoxy-3-Methyl-;methoxy-3-methyl-phenol
    3. CAS NO:14786-82-4
    4. Molecular Formula: C8H10O2
    5. Molecular Weight: 138.1638
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 14786-82-4.mol
  • Chemical Properties

    1. Melting Point: 44-45 °C
    2. Boiling Point: 244.7 °C at 760 mmHg
    3. Flash Point: 121.9 °C
    4. Appearance: /
    5. Density: 1.078 g/cm3
    6. Vapor Pressure: 0.0191mmHg at 25°C
    7. Refractive Index: 1.53
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. PKA: 10.56±0.18(Predicted)
    11. CAS DataBase Reference: 4-methoxy-3-methyl-phenol(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-methoxy-3-methyl-phenol(14786-82-4)
    13. EPA Substance Registry System: 4-methoxy-3-methyl-phenol(14786-82-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 14786-82-4(Hazardous Substances Data)

14786-82-4 Usage

Uses

Used in Chemical Production:
4-methoxy-3-methylphenol is used as a precursor in the synthesis of various chemicals, most notably vanillin, a widely used flavoring agent. Its role in the production of vanillin is crucial, as it serves as a starting material for the creation of this popular flavor compound.
Used in Pharmaceutical Applications:
Guaiacol is utilized in the pharmaceutical industry for its potential antioxidant and anti-inflammatory properties. These characteristics make it a valuable compound for the development of medications aimed at treating conditions that involve oxidative stress and inflammation.
Used in the Food Industry:
In the food industry, 4-methoxy-3-methylphenol is employed as a preservative and flavoring agent. Its smoky flavor profile is particularly desirable in the production of smoked meats and cheeses, where it helps to impart a characteristic taste and aroma to these products.
Overall, 4-methoxy-3-methylphenol, or guaiacol, is a versatile compound with applications in chemical synthesis, pharmaceutical development, and food preservation and flavoring. Its distinctive properties and potential health benefits make it an important substance in these various fields.

Check Digit Verification of cas no

The CAS Registry Mumber 14786-82-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,7,8 and 6 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 14786-82:
(7*1)+(6*4)+(5*7)+(4*8)+(3*6)+(2*8)+(1*2)=134
134 % 10 = 4
So 14786-82-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O2/c1-6-5-7(9)3-4-8(6)10-2/h3-5,9H,1-2H3

14786-82-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methoxy-3-methylphenol

1.2 Other means of identification

Product number -
Other names 4-methoxy-3-methylphenol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:14786-82-4 SDS

14786-82-4Relevant articles and documents

Towards the rational design of novel charge-transfer materials: Biaryls with a dihedral angle-independent hole delocalization mechanism

Ivanova, Lena V.,Navale, Tushar S.,Wang, Denan,Lindeman, Sergey,Ivanov, Maxim V.,Rathore, Rajendra

, p. 5851 - 5854 (2018)

Biaryl cation radicals are important electroactive materials, which show two mechanisms of hole delocalization: static delocalization at small interplanar dihedral angles and dynamic hopping at larger angles, reflecting the interplay between electronic coupling and structural reorganization. Herein, we describe the rational design of biaryls possessing an invariant hole delocalization mechanism.

Catalytic Asymmetric Total Synthesis of (+)- and (-)-Paeoveitol via a Hetero-Diels-Alder Reaction

Li, Tian-Ze,Geng, Chang-An,Yin, Xiu-Juan,Yang, Tong-Hua,Chen, Xing-Long,Huang, Xiao-Yan,Ma, Yun-Bao,Zhang, Xue-Mei,Chen, Ji-Jun

, p. 429 - 431 (2017)

The first catalytic asymmetric total synthesis of (+)- and (-)-paeoveitol has been accomplished in 42% overall yield via a biomimetic hetero-Diels-Alder reaction. The chiral phosphoric acid catalyzed hetero-Diels-Alder reaction showed excellent diastereo-

Fabricating Bifunctional Co?Al2O3@USY Catalyst via In-Situ Growth Method for Mild Hydrodeoxygenation of Lignin to Naphthenes

Cheng, Shuai,Diao, Xinyong,Ji, Na,Jia, Zhichao,Li, Hanyang,Ri, Poknam,Wang, Shurong

, (2022/05/07)

To enhance the catalytic activity and stability of metal catalysts in the hydrodeoxygenation of lignin derivatives into naphthenes, a bifunctional Co?Al2O3@USY catalyst was fabricated by the reduction of CoAl layered double hydroxide in-situ grown on the USY zeolite. In the hydrodeoxygenation of guaiacol, a 100.0 % conversion with cyclohexane yield up to 93.6 % was achieved at 180 °C, 3 MPa for 4 h, which should be the hitherto lowest reaction temperature that has been reported over Co-based metal catalysts. This catalyst was also relatively stable with 5 runs and exhibited excellent catalytic performance in the hydrodeoxygenation of other lignin model compounds and even real lignin feedstock into naphthenes. The high-efficiency of Co?Al2O3@USY was attributed to the synergistic effect between well-dispersed small Co nanoparticles and abundant acidic sites on the USY surface, while the outstanding stability was attributed to the anchoring effect of Al2O3 matrix to Co nanoparticles which avoided the leaching of Co species and particle agglomeration. This work provides a potential strategy for the design of an efficient and stable catalyst for lignin utilization.

Synthetic method 4 - alkoxyphenol compounds

-

Paragraph 0073-0075, (2021/09/29)

The invention discloses a synthetic method of 4 - alkoxyphenol compounds, and belongs to the field of organic chemical synthesis. The method is as follows: An aryl alkyl ether compound is added to the sealing tube. The catalyst dimerization acetic acid rhodium and the oxidizing agent iodobenzene diethyl ester are added, a solvent trifluoroacetic anhydride is added, and the 4 -alkoxyphenol compound is prepared by heating reaction. To the invention, high regioselectivity direct hydroxylation of the aryl alkyl ether compound is realized, the application range of the substrate is wide, the yield is high, the activity after amplification reaction does not significantly decay, and higher yield is still obtained. The utility model has good practicability and industrial application prospect.

Para -Selective hydroxylation of alkyl aryl ethers

Zhu, Runqing,Sun, Qianqian,Li, Jing,Li, Luohao,Gao, Qinghe,Wang, Yakun,Fang, Lizhen

supporting information, p. 13190 - 13193 (2021/12/16)

para-Selective hydroxylation of alkyl aryl ethers is established, which proceeds with a ruthenium(ii) catalyst, hypervalent iodine(iii) and trifluoroacetic anhydride via a radical mechanism. This protocol tolerates a wide scope of substrates and provides a facile and efficient method for preparing clinical drugs monobenzone and pramocaine on a gram scale.

Discovery of 5,6-Bis(4-methoxy-3-methylphenyl)pyridin-2-amine as a WSB1 Degrader to Inhibit Cancer Cell Metastasis

Che, Jinxin,Jin, Zegao,Yan, Fangjie,You, Jieqiong,Xie, Jiangfeng,Chen, Binhui,Cheng, Gang,Zhu, Hong,He, Qiaojun,Hu, Yongzhou,Yang, Bo,Cao, Ji,Dong, Xiaowu

, p. 8621 - 8643 (2021/06/28)

The gain of cell motility is an essential prerequisite for cancer metastasis. The ubiquitin ligase subunit WD repeat and SOCS box-containing 1 (WSB1) has been demonstrated to regulate hypoxia-driven tumor cell migration. However, there is still a lack of methods for discovering inhibitors targeting the WSB1 axis. Here, we employed phenotypic screening models and identified compound4that displayed migration inhibitory activity against WSB1-overexpressing cells. Further studies indicated that it may function as a WSB1 degrader, thus leading to the accumulation of the Rho guanosine diphosphate dissociation inhibitor 2 (RhoGDI2) protein, reversing the expression of downstream F-actin and formation of membrane ruffles, and disturbing the migration capacity of cancer cells. Moreover, compound4exhibited a promisingin vivoanticancer metastatic effects. Our findings show the discovery of a new WSB1 degrader, providing a unique solution for the treatment of cancer metastasis.

Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A

Liu, Feipeng,Dong, Zhe,Wang, Jianchun,Dong, Guangbin

supporting information, p. 2144 - 2148 (2019/01/24)

To show the synthetic utility of palladium/norbornene (Pd/NBE) cooperative catalysis, here we report concise syntheses of indenone-based natural products, pauciflorol F and acredinone A, which are enabled by direct annulation between aryl iodides and unsa

Synthesis of Highly Enantio-Enriched Heliespirones A and C by a Diastereoselective Aromatic Claisen Rearrangement

Norcott, Philip,McErlean, Christopher S. P.

, p. 366 - 372 (2018/05/31)

Computational methods were used to investigate the stereochemical course of the extra-annular Claisen rearrangement. The stereochemical fidelity of the synthetic strategy and comparison of the optical properties support the hypothesis that the heliespirones are scalemic natural products.

Tuning the Reactivity of Peroxo Anhydrides for Aromatic C-H Bond Oxidation

Pilevar, Afsaneh,Hosseini, Abolfazl,?ekutor, Marina,Hausmann, Heike,Becker, Jonathan,Turke, Kevin,Schreiner, Peter R.

, p. 10070 - 10079 (2018/09/06)

Phenol moieties are key structural motifs in many areas of chemical research from polymers to pharmaceuticals. Herein, we report on the design and use of a structurally demanding cyclic peroxide (spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione, P4) for the direct hydroxylation of aromatic substrates. The new peroxide benefits from high thermal stability and can be synthesized from readily available starting materials. The aromatic C-H oxidation using P4 exhibits generally good yields (up to 96%) and appreciable regioselectivities.

Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants

Munday, Samuel D.,Dezvarei, Shaghayegh,Lau, Ian C.-K.,Bell, Stephen G.

, p. 2512 - 2522 (2017/07/12)

Cytochrome P450 CYP102A1 (P450 Bm3) variants were used to investigate the products arising from the P450 catalysed oxidation of a range of disubstituted benzenes. The variants used all generated increased levels of metabolites compared to the wild-type enzyme. With ortho-halotoluenes up to six different metabolites could be identified whereas the oxidation of 2-methoxytoluene generated only two aromatic oxidation products. Addition of an ethyl group markedly shifted the selectivity for oxidation to the more reactive benzylic position. Epoxidation of an alkene was also preferred to aromatic oxidation in 2-methylstyrene. Significant minor products arising from the migration of one substituent to a different position on the benzene ring were formed during certain P450-catalysed substrate turnovers. For example, 2-bromo-6-methylphenol was formed from the turnover of 2-bromotoluene and the dearomatisation product 6-ethyl-6-methylcyclohex-2,4-dienone was generated from the oxidation of 2-ethyltoluene. The RLYF/A330P variant altered the product distribution enabling the generation of certain metabolites in higher quantities. Using this variant produced 4-methyl-2-ethylphenol from 3-ethyltoluene with ≥90 % selectivity and with a biocatalytic activity suitable for scale-up of the reaction.

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