54344-92-2

Basic information

• Product Name: 4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE
• Synonyms: 4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE;CHEMBRDG-BB 5229799;TIMTEC-BB SBB010628;2,3,6-trimethyl-p-anisaldehyde;2,3,6-Trimethyl-p-anisaldehyd;4-metoxy-2,3,6-trimetylbenzaldehyde;4-methoxy-2,3,6-trimethylbenzaldehyde(SALTDATA: FREE)
• CAS NO: 54344-92-2
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• EINECS: 259-117-2
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aromatics
• Mol File: 54344-92-2.mol

Chemical Properties

• Melting Point: 63.0 to 68.0 °C
• Boiling Point: 301.2 °C at 760 mmHg
• Flash Point: 133.4 °C
• Appearance: White Crystaline Solid
• Density: 1.024 g/cm³
• Vapor Pressure: 0.00107mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Tetrahydrofuran
• CAS DataBase Reference: 4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE(54344-92-2)
• EPA Substance Registry System: 4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE(54344-92-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 54344-92-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block for the creation of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Fragrance Industry:
4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE is used as a fragrance ingredient in the perfumery industry. Its distinct aroma profile makes it a valuable component in the formulation of various fragrances, contributing to the overall scent profile of perfumes, colognes, and other scented products.
Used in Flavor Industry:
4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE is also used as a flavoring agent in the food and beverage industry. Its unique taste and aroma characteristics can be utilized to enhance the flavor of various products, such as candies, beverages, and other confectionery items.
Used in Pharmaceutical Industry:
4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds. Its chemical properties make it suitable for the development of new drugs and active pharmaceutical ingredients (APIs) with potential therapeutic applications.
Used in Dye and Pigment Industry:
4-METHOXY-2,3,6-TRIMETHYL-BENZALDEHYDE is used as a precursor in the production of dyes and pigments. Its chemical structure can be modified to create a range of colored compounds that can be used in various applications, such as textiles, plastics, and coatings.

InChI:InChI=1/C11H14O2/c1-7-5-11(13-4)9(3)8(2)10(7)6-12/h5-6H,1-4H3

Upstream product

• 20469-61-8 2,3,5-trimethylanisole 
• 68-12-2 N,N-dimethyl-formamide 
• 697-82-5 2,3,5-trimethylphenol 
• 74-88-4 methyl iodide 
• 154152-57-5 4-bromo-3-nitro-1,2,5-trimethylbenzene 
• 767-77-1 2,3,5-trimethylaniline 
• 5469-19-2 1-bromo-2,4,5-trimethylbenzene 
• 4885-02-3 Dichloromethyl methyl ether 

Downstream Products

• 63651-12-7 4-(4-methoxy-2,3,6-trimethylphenyl)-1,1,1-trifluoro-2-butyn-4-ol 
• 54757-46-9 acitretin 
• 54757-48-1 5-(4-methoxy-2,3,6 trimethylphenyl)-3-methylpenta-1,4-dien-3-ol 
• 54757-44-7 5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-diene-1-triphenylphosphonium bromide 
• 74479-40-6 butyl {(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl)phenyl-3,7-dimethylnona-2,4,6.8}tetraenoate 
• 63651-23-0 (Z)-2-Fluoro-3-(4-methoxy-2,3,6-trimethyl-phenyl)-acrylic acid 
• 20469-61-8 2,3,5-trimethylanisole 
• 1621283-94-0 2,3,6,2’,3’,6’-hexamethyl-4,4’-dihydroxy-trans-stilbene 
• 1621283-98-4 2,3,6,2’,3’,6’-hexamethyl-4,4’-dimethoxy-trans-stilbene 
• 1621283-97-3 4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylphenol) 
• 1621284-01-2 4,4’-((1E,3E,5E,7E,9E,11E,13E)-3,7,12-trimethyltetradeca-1,3,5,7,9,11,13-heptaene-1,14-diyl)bis(1-methoxy-2,3,5-trimethylbenzene) 
• 58508-38-6 (2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenal 
• 61630-49-7 (2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraen-1-ol 
• 54350-48-0 etretinate 

Relevant articles and documents

Design, synthesis, biological activities and DFT calculation of novel 1,2,4-triazole Schiff base derivatives

Series of 1,2,4-triazole Schiff bases (2a-2d, 2f-2h and 3a-3h) have been designed and synthesized. The structure of title compounds was confirmed on the basis of their spectral data and elemental analysis. All the target compounds were screened for their in vitro antifungal activity and antibacterial activity. Two of the tested compounds (2a and 2b) exhibited significant antifungal activity against most fungi, especially compound 2a showed better antifungal activity than triadimefon. Meanwhile, the antibacterial activity assay also indicated compound 2a exhibited excellent antibacterial activities comparable to chloramphenicol. The SAR manifested no substitution at position 5 of the triazole ring caused an increase in activity, and 3-phenoxy phenyl group introduced in 1,2,4-triazole scaffold can enhance the antibacterial activity. The DFT calculation indicated triazole ring, S atom and benzene ring in both of the 2a and 3a make a major contribution to the activity.

Tailoring 3,3'-dihydroxyisorenieratene to hydroxystilbene: Finding a resveratrol analogue with increased antiproliferation activity and cell selectivity

Four novel compounds were designed by "tailoring" 3,3'-dihydroxyisorenieratene (a natural carotenoid) based on an isoprene unit retention truncation strategy. Among them, the smallest molecule 1 (2,3,6,2',3',6'-hexamethyl-4,4'-dihydroxy-trans-stilbene) was concisely synthesized in a one-pot Stille-Heck tandem sequence, and surfaced as a promising lead molecule in terms of its selective antiproliferative activity mediated by blocking the NCI-H460 cell cycle in G1 phase. Additionally, theoretical calculations and cell uptake experiments indicate that the unique polymethylation pattern of compound 1 significantly induces a conformational change shift out of planarity and increases its cell uptake and metabolic stability. The observation should be helpful to rationally design resveratrol-inspired antiproliferative agents. Four novel compounds were designed by "tailoring" 3,3'-dihydroxyisorenieratene (a natural carotenoid) based on an isoprene unit retention truncation strategy. Among them, the smallest molecule 1 was concisely synthesized by a one-pot Stille-Heck tandem sequence, and surfaced as a promising lead molecule in terms of its selective antiproliferative activity (see figure).

One-pot synthesis of pyrimidinothiazolidinones and their anti-inflammatory and antimicrobial studies

In the present investigation, we report a one-pot synthesis of the title compounds, 2-arylidene-5-(2,3,6-trimethyl-4-methoxyphenyl)-7-substituted-5H- pyrimidino-[2,3-b]thiazolidine-3-ones 6a-j and 2-(5-nitro-2-thienylidine)-5-(2, 3,6-trimethyl-4-methoxyphenyl)-7-substituted-5H- pyrimidino-[2,3-b]thiazolidine- 3-ones 7a-e. Thus, 6a-j and 7a-e were prepared in good yields by refluxing 4-(2,3,6-trimethyl-4-methoxyphenyl)-6-methyl/aryl-3,4-dihydropyrimidin-2-(1H) -thiones 5, monochloro acetic acid, and anhydrous sodium acetate with the appropriate aromatic aldehyde/5-nitro-2-thiophenediacetate in acetic acid/acetic anhydride medium. The structures of these new compounds were established on the basis of their analytical and spectral data. Some of the newly synthesized compounds were screened for their anti-inflammatory and antimicrobial activity. They show moderate anti-inflammatory activity, and some of them were found to be promising antibacterial and antifungal agents. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

A new stereoselective synthesis of acitretin (=Soriatane, Neotigason)

A new synthesis of acitretin via a C15 + C5 route is reported. The C15 unit is the key step, involving a procedure that provides the required (all-E)-C15-aldehyde with high stereoselectivity.

Evaluation of retinoid lactones as topical therapeutic agents in dermatology

Purpose. Optimization of the therapeutic ratio of analogs of the topically active 11-cis,13-cis-12-hydroxymethylretinoic acid, δ-lactone (I) relative to antihyperproliferation and antihyperkeratinization vs. toxicity. Methods. Nine analogs of 1, in which variations were made in the lipophilic cyclohexenyl moiety or in the lactone ring, were evaluated for topical activity against hyperkeratinization, inhibition of TPA-induced DNA synthesis and for skin irritation. Results. Although more potent lactones than the parent lactone 1 were identified, none possessed the favorable therapeutic ratio associated with 1. Conclusions. The δ-lactone 1 possesses unique molecular features responsible for its desirable therapeutic ratio as an anti-hyperproliferative and antihyperkeratotic agent. In view of its very low systemic retinoid toxicity and the absence of any systemic toxicity, this lactone may be a good candidate for use in the topical treatment of acne.

STEREOSELECTIVE SYNTHESIS OF 5-ARYL-3-METHYL-2E,4E-PENTADIENALS

A series of 5-aryl-3-methyl-2E,4E-pentadienals were synthesized stereoselectively from 4-aryl-3E-buten-2-ones and methylmagnesium iodide followed by formylation of the obtained tertiary dimethylstyrylcarbinols by the formylating complex produced from dimethylformamide and phosphorus oxychloride.A synthesis of 2,3,6-trimethyl-4-methoxybenzaldehyde, starting from pseudocumene, is proposed.

Antidandruff compositions containing 9-(4-lower alkoxy-2,3,6-trilower-alkylphenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid lower alkyl amides

Compositions suitable for the care of the hair and scalp particularly with respect to the control of dandruff are disclosed. Said compositions comprise a suitable inert carrier and, as an active ingredient, a compound selected from those represented by the formula STR1 wherein R1, R2, R3, R4 and R6 are lower alkyl.