69877-38-9

Usage

Uses

Used in Perfumery and Aromatics Industry:
(2E,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal is used as a fragrance ingredient for its characteristic aroma, which contributes to the pleasant scent of perfumes and aromas. Its natural origin and unique scent profile make it a valuable component in creating complex and long-lasting fragrances.
Used in Pharmaceutical Development:
(2E,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal is used as a potential active pharmaceutical ingredient due to its antioxidant and antimicrobial properties. Its ability to combat oxidative stress and inhibit microbial growth makes it a promising candidate for the development of new drugs, particularly in the treatment of various diseases and conditions.
Used in Food Additives Industry:
(2E,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal is used as a flavoring agent in the food additives industry. Its natural aroma and flavor enhance the taste and appeal of various food products, providing a unique and desirable sensory experience for consumers.
Used in Organic Synthesis:
(2E,4E)-5-(4-Methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienal serves as a key intermediate in the synthesis of various organic compounds. Its unique chemical structure allows for further reactions and modifications, making it a versatile building block in the development of new chemical entities and materials.

InChI:InChI=1/C16H20O2/c1-11(8-9-17)6-7-15-12(2)10-16(18-5)14(4)13(15)3/h6-10H,1-5H3/b7-6+,11-8+

Upstream product

• 5927-18-4 trimethyl phosphonoacetate 
• 62924-31-6 1-(2,5,6-trimethyl-4-methoxyphenyl)-but-1-en-3-one 
• 68-12-2 N,N-dimethyl-formamide 
• 167637-42-5 5-(4'-methoxy-2',3',6'-trimethylphenyl)-3-methylpenta-2,4-dienol 
• 478496-90-1 (4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylidenepent-4-enal 
• 478496-91-2 (1E)-5,5-dimethoxy-1-(4-methoxy-2,3,6-trimethylphenyl)pent-1-en-3-one 
• 478496-92-3 2-[(1E)-3-(2,2-dimethoxyethyl)buta-1,3-dienyl]-5-methoxy-1,3,4-trimethylbenzene 
• 20469-61-8 2,3,5-trimethylanisole 
• 697-82-5 2,3,5-trimethylphenol 
• 54344-92-2 2,3,6-trimethyl-4-methoxy-benzaldehyde 
• 54757-47-0 4-(4'-methoxy-2',3',6'-trimethylphenyl)-but-3-ene-2-one 
• 167637-41-4 ethyl 3-methyl-5-(4'-methoxy-2',3',6'-trimethylphenyl)-2,4-pentadienoate 
• 5469-19-2 1-bromo-2,4,5-trimethylbenzene 
• 767-77-1 2,3,5-trimethylaniline 

Downstream Products

• 63651-18-3 7-(4-methoxy-2,3,6-trimethylphenyl)-2-fluoro-5-methyl-2(Z),4(E),6(E)-heptatrienoic acid, ethyl ester 
• 63700-90-3 9-(4-methoxy-2,3,6-trimethylphenyl)-4-fluoro-3,7-dimethyl-2(E),4(E),6(E),8(E)-nonatetraenoic acid ethyl ester 
• 54350-48-0 etretinate 
• 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) 
• 1621283-96-2 4,4’-((1E,3E,5E,7E,9E)-3,8-dimethyldeca-1,3,5,7,9-pentaene-1,10-diyl)bis(2,3,5-trimethylphenol) 
• 1621284-00-1 4,4’-((1E,3E,5E,7E,9E)-3,8-dimethyldeca-1,3,5,7,9-pentaene-1,10-diyl)bis(1-methoxy-2,3,5-trimethylbenzene) 
• 127644-85-3 (2Z,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid methyl ester 
• 127644-91-1 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2Z,4E,6E,8E-nonatetraenal 
• 127644-88-6 (2Z,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-ol 
• 69427-46-9 13-cis-Acitretin 
• 61630-49-7 (2E,4E,6E,8E)-9-(4-methoxyl-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraen-1-ol 
• 74479-45-1 9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraen-1-oic acid methyl ester 
• 54757-46-9 acitretin 

Relevant academic research and scientific papers

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).

Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 μM. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability.

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.

Polyene compounds useful in the treatment of allergic responses

Polyene compounds represented by the formula STR1 where R is H or lower alkyl of from 1 to 5 carbon atoms; R1 is H, lower alkyl of from 1 to 8 carbon atoms or aralkyl; and R2 is (CH2)n CH2 OH, CHO or CO2 R; wherein n is 1 or 2. The foregoing compounds have been found active in regulating the formation of lipoxygenase and as such possess therapeutic value in the treatment of inflammatory conditions and allergic responses.

Fluorinated aromatic polyenes

Compounds represented by the formula STR1 wherein R1, R2 and R3 are lower alkyl, R4 is lower alkoxy, R6 and R8 are methyl or trifluoro methyl, R9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R5, R7, R10, R11, R12 and R13 are hydrogen or fluorine with the proviso that at least one of R5, R7, R10, R11, R12 or R13 is fluorine or at least one of R6 or R8 is trifluoro methyl, or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.