99217-07-9

Upstream product

• 5273-86-9 C₁₂H₁₆O₃ 
• 4460-86-0 asaraldehyde 
• 75-07-0 acetaldehyde 
• 6906-65-6 1-propyl-2,4,5-trimethoxybenzene 
• 5353-15-1 1-allyl-2,4,5-trimethoxybenzene 
• 2883-98-9 α-asarone 
• 1392497-89-0 3-(2,4,5-trimethoxyphenyl)-(2E)-2-propen-1-ol 
• 14469-89-7 trans-2,4,5-trimethoxycinnamic acid ethyl ester 

Downstream Products

• 1380294-19-8 (E)-N-(1-(2,4,5-trimethoxyphenyl)hexa-1,5-dien-3-yl)acrylamide 
• 1380294-27-8 (E)-6-(2,4,5-trimethoxystyryl)-5,6-dihydropyridin-2(1H)-one 
• 1380294-02-9 (E)-1-(2,4,5-trimethoxyphenyl)hexa-1,5-dien-3-yl acrylate 
• 1380294-10-9 (E)-6-(2,4,5-trimethoxystyryl)-5,6-dihydro-2H-pyran-2-one 
• 1380293-94-6 (E)-1-(2,4,5-trimethoxyphenyl)hexa-1,5-dien-3-ol 
• 5353-15-1 1-allyl-2,4,5-trimethoxybenzene 
• 80749-75-3 (E)-3-(2,4,5-trimethoxy-phenyl)-acrylic acid methyl ester 
• 437761-99-4 2,4,5-trimethoxycinnamyltosylhydrazone 

Relevant academic research and scientific papers

Ultrasound-assisted convenient synthesis of hypolipidemic active natural methoxylated (E)-arylalkenes and arylalkanones

An ultrasound-assisted convenient method was developed for the conversion of toxic methoxylated cis-isomer of arylalkenes into its hypolipidemic active trans-isomer. Treatment of cis-isomer or mixture of all three isomers (1a-1j) with ammonium formate and 10% Pd/C gave arylalkanes (2a-2j), which upon oxidation with DDQ in anhydrous dioxane containing a little amount of silica gel, provided (E)-arylalkenes (3a-3g) in 42-72% yield depending upon the substituents attached at the aryl ring. The same method, upon addition of a few drops of water, provided hypolipidemic active arylalkanones (3h-3j) in 59-65% yield.

Phenyl indane from acorus calamus

Besides three known compounds, two new compounds, namely Z-3-(2,4,5-trimethoxy phenyl)-2-propenal and a new phenyl indane have been isolated from the rhizomes of Acorus calamus. These compounds have been characterized from their spectral data and by synthesis.

Synthesis and SAR investigation of natural phenylpropene-derived methoxylated cinnamaldehydes and their novel Schiff bases as potent antimicrobial and antioxidant agents

A series of cinnamyl compounds were synthesized from abundantly available methoxylated phenylpropenes and evaluated for their antimicrobial activity by the broth microdilution method against fourteen opportunistic bacterial and fungal human pathogens. Structure-activity relationship studies indicated that methylenedioxy cinnamaldehyde exhibited promising broad-spectrum activity against the tested microorganisms and hence was used as a lead structure to synthesize novel Schiff bases/heterocyclic compounds (23-33) under microwave irradiation. Out of these, thiazole-based Schiff bases have shown promising antibacterial activity against B. subtilis (26; MIC 0.12 mM), M. luteus (27; MIC 0.20 mM), and S. aureus (27; MIC 0.20 mM). Also, the compounds 23-33 were investigated for in vitro antioxidant activity using DPPH? assay where compound 28 showed a maximum of 80.71 % inhibition.

Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the γ-pyrones and the aza-goniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin (1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds.

Efficient one-pot, two-step synthesis of (E)-cinnmaldehydes by dehydrogenation-oxidation of arylpropanes using DDQ under ultrasonic irradiation

A general, efficient and new approach to the synthesis of cinnamaldehydes with trans-selectivity has been accomplished starting from arylpropanes. One-pot, two-step dehydrogenation and oxidation of arylpropanes with excess DDQ in dioxane containing a few drops of acetic acid gave (E)-cinnmaldehydes under ultrasound irradiation.

Process for the preparation of pharmacologically active α-asarone from toxic β-asarone rich acorus calamus oil

The present invention relates to a process for the preparation of high purity and yield α-asarone, trans 2,4,5-trimethoxy cinnamaldehyde, 2,4,5-trimethoxy-phenyl propionone, from β-asarone or β-asarone rich Acorus calamus oil containing α and γ-asarone by hydrogenating, followed by treatment with DDQ with or without solid support of silica gel or alumina in dry organic solvent and α-asarone can also be obtained by treating the hydrogenated product of β-asarone or β-asarone rich Acorus calamus with DDQ in an aqueous organic solvent to obtain an intermediate 2,4,5-trimethoxy phenyl propionone, which in turn is reduced with sodiumborohydride to obtain the corresponding 2,4,5-trimethoxy-phenyl propanol and followed by final treatment with a dehydrating agent.

A PROCESS FOR THE PREPARATION OF PHARMACOLOGICALLY ACTIVE ALPHA-ASARONE FROM TOXIC BETA-ASARONE RICH ACORUS CALAMUS OIL

The present invention relates to a process for the preparation of high purity and yield α-asarone, trans 2,4,5-trimethoxy cinnamaldehyde, 2,4,5-trimethoxy-phenyl propionone, from β-asarone or β-asarone rich Acorus calamus oil containing α and γ-asarone by hydrogenating, followed by treatment with DDQ with or without solid support of silica gel or alumina in dry organic solvent and α-asarone can also be obtained by treating the hydrogenated product of β-asarone or β-asarone rich Acorus calamus with DDQ in an aqueous organic solvent to obtain an intermediate 2,4,5-trimethoxy phenyl propionone, which in turn is reduced with sodiumborohydride to obtain the corresponding 2,4,5-trimethoxy-phenyl propanol and followed by final treatment with a dehydrating agent.

A mild and convenient procedure for the conversion of toxic β-asarone into rare phenylpropanoids: 2,4,5-Trimethoxycinnamaldehyde and γ-asarone

Oxidation of β-asarone (2) with DDQ gave trans-2,4,5- trimethoxycinnamaldehyde (3), which on treatment with p-toluenesulfonyl hydrazine provided corresponding α,β-unsaturated hydrazone derivative (4). Reduction of 4 with sodium borohydride in acetic acid afforded γ-asarone (1) in 43% yield.

Process for the preparation of substituted trans-cinnamaldehyde, a natural yellow dye, from phenylpropane derivatives

The present invention relates to the preparation of substituted trans-cinnamaldehyde, a natural yellow dye from Phenylpropane derivatives having R2-R3-R4-R5-R6 substitution, wherein R2 to R6 equal or different, being hydrogen or hydroxy or acyl or halogen or alkyl or heterocyclic or aryl or dioxymethylene or alkoxy groups, etc., by oxidizing the said phenylpropane derivatives using a oxidising agent such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or p-chloranil or pyridinium chlorochromate (PCC) or tBuOOH or or CrO3 with a catalytic amount of inorganic/organic acid or alumina, celite, and silica gel as a solid support for microwave irradiation and thus substituted trans-cinnamaldehydes, a natural yellow dye, are obtained in high yield ranging from 68-82%.

2,4,5-Trimethoxycinnamaldehyde from Caesulia axillaris Roxb.

Acetone extract of Caesulia axillaris Roxb. has yielded a new aromatic 2,4,5-trimethoxycinnamaldehyde along with the known γ-asarone and 2,4,5-trimethoxycinnamaldehyde.The structure of the new aldehyde has been established by spectral data and synthesis.