20733-94-2

Basic information

• Product Name: antithiamine factor
• Synonyms: antithiamine factor;METHYLSINAPATE;3-(4-Hydroxy-3,5-dimethoxyphenyl)propenoic acid methyl ester;3,5-Dimethoxy-4-hydroxybenzeneacrylic acid methyl ester;Methyl 4-hydroxy-3,5-dimethoxycinnamate;Sinapic acid methyl ester;Methyl 3-(4-hydroxy-3,5-diMethoxyphenyl)acrylate
• CAS NO: 20733-94-2
• Molecular Formula: C₁₂H₁₄O₅
• Molecular Weight: 238.24
• Mol File: 20733-94-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 89.9-90.7 °C(Solv: carbon tetrachloride (56-23-5))
• Boiling Point: 372.3°Cat760mmHg
• Flash Point: 140.6°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 4.55E-06mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.90±0.23(Predicted)
• CAS DataBase Reference: antithiamine factor(CAS DataBase Reference)
• NIST Chemistry Reference: antithiamine factor(20733-94-2)
• EPA Substance Registry System: antithiamine factor(20733-94-2)

Safety Data

• Hazardous Substances Data: 20733-94-2(Hazardous Substances Data)

Usage

General Description

The "antithiamine factor" refers to a group of chemicals that can inhibit the absorption and utilization of thiamine, also known as vitamin B1, in the body. These compounds, which include polyhydroxyphenols and certain sulfur-containing compounds, can be found in raw freshwater fish, shellfish, and ferns, as well as in certain plants and grains such as tea leaves, coffee beans, and betel nuts. When consumed in sufficient quantities, the antithiamine factor can lead to thiamine deficiency and potentially result in symptoms such as fatigue, irritability, and muscle weakness.

InChI:InChI=1/C12H14O5/c1-15-9-6-8(4-5-11(13)17-3)7-10(16-2)12(9)14/h4-7,14H,1-3H3/b5-4+

Upstream product

• 134-96-3 syringic aldehyde 
• 530-59-6 sinapinic acid 
• 75-36-5 acetyl chloride 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 

Downstream Products

• 530-59-6 sinapinic acid 
• 1316855-24-9 methyl (E)-3-[2-(4-hydroxy-3,5-dimethoxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]propen-2-enoate 
• 1316855-25-0 C₂₄H₂₈O₁₀ 
• 1316855-26-1 methyl (E)-3-[2-(4-hydroxy-3,5-dimethoxyphenyl)-3-methoxycarbonyl-2,3-dihydro-1-4-benzodioxan-7-yl]propen-2-enoate 
• 1316855-23-8 methyl (E)-3-[2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]propen-2-enoate 
• 487-35-4 (+/-)-syringaresinol 
• 20675-96-1 Syringenin 
• 1240483-58-2 8-(4-hydroxy-3,5-dimethoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromen-6-one 

Relevant articles and documents

Colorimetric and ratiometric sensors derivated from natural building blocks for fluoride ion detection

Three novel colorimetric and ratiometric probes (SH-1~3) for fluoride ion detection were designed and synthesized from nature small molecules. Obvious yellow-to-orange color change of these probes in the THF was achieved only in presence of F?

Antifungal activity of cinnamic acid and benzoic acid esters against Candida albicans strains

Candida albicans is an important opportunistic fungal pathogen capable of provoking infection in humans. In the present study, we evaluated the antifungal effect of 23 ester derivatives of the cinnamic and benzoic acids against 3 C. albicans strains (ATCC-76645, LM-106 and LM-23), as well as discuss their Structure–Activity Relationship (SAR). The antifungal assay results revealed that the screened compounds exhibited different levels of activity depending on structural variation. Among the ester analogues, methyl caffeate (5) and methyl 2-nitrocinnamate (10) were the analogues that presented the best antifungal effect against all C. albicans strains, presenting the same MIC values (MIC?=?128?μg/mL), followed by methyl biphenyl-2-carboxylate (21) (MIC?=?128, 128 and 256?μg/mL for C. albicans LM-106, LM-23, and ATCC-76645, respectively). Our results suggest that certain molecular characteristics are important for the antifungal action.

Chemical interaction between polyphenols and a cysteinyl thiol under radical oxidation conditions

Chemical interaction between polyphenols and thiols was investigated under radical oxidation conditions using a model cysteinyl thiol derivative, N-benzoylcysteine methyl ester. The radical oxidation was carried out with a stoichiometric amount of 2,2-diphenyl-1-picrylhydrazyl (DPPH), and the decreases in the amounts of polyphenols and the thiol were measured by HPLC analysis. Cross-coupling products between various polyphenols and the thiol were examined by LC-MS in reactions that showed decreases in both the polyphenols and the thiol. The LC-MS results indicated that three phenolic acid esters (methyl caffeate, methyl dihydrocaffeate, and methyl protocatechuate) and six flavonoids (kaempferol, myricetin, luteolin, morin, taxifolin, and catechin) gave corresponding thiol adducts, whereas three polyphenols (methyl ferulate, methyl sinapate, and quercetin) gave only dimers or simple oxidation products without thiol substituents. Thiol adducts of the structurally related compounds methyl caffeate and methyl dihydrocaffeate were isolated, and their chemical structures were determined by NMR analysis. The mechanism for the thiol addition was discussed on the basis of the structures of the products.