26350-60-7

Basic information

• Product Name: Thomasidioic acid
• Synonyms: (±)-Thomasidioic acid;Thomasidioic acid
• CAS NO: 26350-60-7
• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.4
• Mol File: 26350-60-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Thomasidioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Thomasidioic acid(26350-60-7)
• EPA Substance Registry System: Thomasidioic acid(26350-60-7)

Safety Data

• Hazardous Substances Data: 26350-60-7(Hazardous Substances Data)

Upstream product

• 530-59-6 trans-3,5-dimethoxy-4-hydroxycinnamic acid 
• 530-59-6 sinapinic acid 
• 42041-51-0 methyl (E)-sinapate 
• 41514-36-7 2,6-bis(4'-hydroxy-3',5'-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-4,8-dione 

Downstream Products

• 530-55-2 2,6-dimethoxy-p-quinone 
• 23204-42-4 6-hydroxy-5,7-dimethoxynaphthalene-2-carboxylic acid 
• 23212-62-6 rac.-Thomasidiosaeure-7,4'-dimethylether-dimethylester 

Relevant articles and documents

Evaluation of alkaline conversion of sinapic acid to thomasidioic acid

Conditions which promote the alkaline conversion of sinapic acid (SA), the main phenolic acid in canola, to the lignan thomasidioic acid (TA) were investigated as the presence of TA could affect nutritional and functional properties of canola products. Re

Structural changes of sinapic acid during alkali-induced air oxidation and the development of colored substances

Structural changes of sinapic acid were induced by air oxidation in aqueous solutions at pH 7-10 and followed by spectral and high-performance liquid chromatographic (HPLC) analysis. Color properties of the sinapic acid solutions were determined by taking

Determination of free diferulic, disinapic and dicoumaric acids in plants and foods

Hydroxycinnamates are common phenolic compounds of plants and plant foods, often found in substantial quantities. Due to their high in vitro antioxidant activity they can easily be oxidized under oxidative conditions. In this study, we found that in vitro

Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fiber

Two 8-8-coupled sinapic acid dehydrodimers and at least three sinapate-ferulate heterodimers have been identified as saponification products from different insoluble and soluble cereal grain dietary fibers. The two 8-8-disinapates were authenticated by comparison of their GC retention times and mass spectra with authentic dehydrodimers synthesized from methyl or ethyl sinapate using two different single-electron metal oxidant systems. The highest amounts (481 μg/g) were found in wild rice insoluble dietary fiber. Model reactions showed that it is unlikely that the dehydrodisinapates detected are artifacts formed from free sinapic acid during the saponification procedure. The dehydrodisinapates presumably derive from radical coupling of sinapate-polymer esters in the cell wall; the radical coupling origin is further confirmed by finding 8-8 and 8-5 (and possibly 8-0-4) sinapate-ferulate cross-products. Sinapates therefore appear to have an analogous role to ferulates in cross-linking polysaccharides in cereal grains and presumably grass cell walls in general.

Thomasidioic acid and 6-hydroxy-5,7-dimethoxy-2-naphthoic acid: Are they really natural products?

It has been shown that air oxidation of alkaline aqueous solutions of sinapic acid produces both thomasidioic acid (1), and 6-hydroxy-5,7-dimethoxy-2-naphthoic acid (2) in high yield, with the relative amounts dependent on the basicity of the solution. It has also been shown that naphthoic acid 2 is a secondary oxidation product of thomasidioic acid, a reaction that also produces 2,6-dimethoxy-p-benzoquione (3). The question of whether compounds 1, 2 and 3 are really natural products, as previously reported, is discussed.