An Efficient Synthesis of 3,4,5-Trimethoxybenzaldehyde from Vanillin

Rao, Durvasula V.; Stuber, F. A.

doi:10.1055/s-1983-30315

Cited by 37 publications

(24 citation statements)

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“…Vanillin has been used to synthesize 3,4,5‐trimethoxybenzaldehyde, a valuable pharmaceutical intermediate, by a three‐step process (Rao and Stuber 1983). In view, those two analogues of TMBA, 1,2,3,4‐tetramethoxy benzene and methyl 3,4,5‐trimethoxy benzoate were simultaneously detected in fruiting bodies.…”

Section: Discussionmentioning

confidence: 99%

Production of a COX-2 inhibitor, 2,4,5-trimethoxybenzaldehyde, with submerged cultured Antrodia camphorata

Chen

Chyau

Hseu

2007

Lett Appl Microbiol

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Aims: To investigate the active ingredient in fruiting bodies and to produce it with cultured mycelium in Antrodia camphorata (BCRC 35398). Methods and Results: The volatile components from the fruiting bodies, the liquid cultured broth of A. camphorata and Cinnamomum kanehirae wood were separately isolated by steam distillation–solvent extraction and identified by gas chromatography–mass spectrometry. In the fruiting bodies, a COX‐2 inhibitor 2,4,5‐trimethoxybenzaldehyde (TMBA) was found to be the most abundant constituent, but was totally absent in its cultured broth and its natural host, C. kanehirae wood. On feeding with the acid‐digested sawdust of C. kanehirae wood or vanillin to the broth for culture, TMBA was produced in both cultured broths. Conclusion: The TMBA identified in fruiting bodies was an active ingredient whose functions consisted with the reported experiences of this mushroom. Feeding vanillin to culture broth could produce TMBA containing mycelium product like its fruiting bodies did. Significance and Impact of the Study: This study found an active ingredient in fruiting bodies of A. camphorata and elucidated this compound derived from digested sawdust of C. kanehirae wood. A feasible method was also developed to produce TMBA containing mycelium by feeding vanillin.

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Section: Discussionmentioning

confidence: 99%

Production of a COX-2 inhibitor, 2,4,5-trimethoxybenzaldehyde, with submerged cultured Antrodia camphorata

Chen

Chyau

Hseu

2007

Lett Appl Microbiol

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“…Syringaldehyde ( M1S ) is a lignin-derived lignin monomer, which can be nearly quantitatively methylated to the corresponding derivative with 96% yield. 440 , 441 (−)-Rhaphidecursinol B ( PN5 ), first isolated from Rhaphidophora decursiva Schott (Araceae), 419 , 442 can be obtained from methylated syringaldehyde ( M1S ) in only three steps. 443 PN5 was found active against Plasmodium falciparum , the parasite responsible for the most severe form of malaria.…”

Section: Compounds With Pharmacological Activity From Lignin-derived mentioning

confidence: 99%

“…Combretastatin derivatives also show antitumor activity, and the Z isomer of PC3 was the most potent derivative in the paper presented by Riant et al 536 It was synthesized from methylated M1S in four steps with 33% yield. M1S can be quantitatively (96%) methylated 440 , 441 which means five steps to PC3 from M1S .…”

Section: Compounds With Pharmacological Activity From Lignin-derived mentioning

confidence: 99%

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Bright Side of Lignin Depolymerization: Toward New Platform Chemicals

et al. 2018

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Lignin, a major component of lignocellulose, is the largest source of aromatic building blocks on the planet and harbors great potential to serve as starting material for the production of biobased products. Despite the initial challenges associated with the robust and irregular structure of lignin, the valorization of this intriguing aromatic biopolymer has come a long way: recently, many creative strategies emerged that deliver defined products via catalytic or biocatalytic depolymerization in good yields. The purpose of this review is to provide insight into these novel approaches and the potential application of such emerging new structures for the synthesis of biobased polymers or pharmacologically active molecules. Existing strategies for functionalization or defunctionalization of lignin-based compounds are also summarized. Following the whole value chain from raw lignocellulose through depolymerization to application whenever possible, specific lignin-based compounds emerge that could be in the future considered as potential lignin-derived platform chemicals.

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“…These 13 C-enriched coniferins are also intended to be used for the preparation of DHPs (Terashima et al 1995), specifically 13 C-enriched at the corresponding position of the guaiacyl ring. It is possible to prepare syringaldehyde-[4-13 C], and syringaldehyde-[3-13 C] from vanillin-[4-13 C] (14) and vanillin-[5-13 C] (27), respectively, by the procedure of Rao and Stuber (1983). Syringin-[4-13 C] and syringin-[3-13 C] can be prepared from these 13 C-syringaldehydes (Terashima et al 1996).…”

Section: Resultsmentioning

confidence: 99%