7345-82-6

Basic information

• Product Name: trans-2,3-Dimethoxycinnamic acid
• Synonyms: TRANS-2,3-DIMETHOXYCINNAMIC ACID;3-(2,3-DIMETHOXYPHENYL)ACRYLIC ACID;LABOTEST-BB LT00452956;DIMETHOXYCINNAMIC-2,3 ACID;(E)-3-(2,3-DIMETHOXY-PHENYL)-ACRYLIC ACID;2,3-Dimethoxycinnamic acid;(Z)-3-(2,4-DIMETHOXYPHENYL)ACRYLIC ACID;trans-2,3-Dimethoxycinnamic acid, 98+%
• CAS NO: 7345-82-6
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21
• EINECS: 231-249-5
• Product Categories: C11 to C12;Carbonyl Compounds;Carboxylic Acids
• Mol File: 7345-82-6.mol

Chemical Properties

• Melting Point: 182-184 °C(lit.)
• Boiling Point: 351.6oC at 760 mmHg
• Flash Point: 136.7oC
• Appearance: /
• Density: 1.203±0.06 g/cm3(Predicted)
• Vapor Pressure: 1.51E-05mmHg at 25°C
• PKA: 4.40±0.10(Predicted)
• BRN: 2695122
• CAS DataBase Reference: trans-2,3-Dimethoxycinnamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-2,3-Dimethoxycinnamic acid(7345-82-6)
• EPA Substance Registry System: trans-2,3-Dimethoxycinnamic acid(7345-82-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 7345-82-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Trans-2,3-Dimethoxycinnamic acid is used as an intermediate in the synthesis of complex organic molecules for pharmaceutical applications. Its unique structure allows for the creation of new compounds with potential therapeutic properties.
Used in Chemical Synthesis:
Trans-2,3-Dimethoxycinnamic acid is used as a building block in the synthesis of various organic compounds, such as (2E,2'E,2''E)-N,N',N''-(nitrilotri-2,1-ethanediyl)tris[3-(2,3-dimethoxyphenyl)-2-propenamide]. trans-2,3-Dimethoxycinnamic acid serves as an example of the versatility of trans-2,3-Dimethoxycinnamic acid in chemical synthesis, where it can be used to create a wide range of molecules with different applications.

InChI:InChI=1/C11H12O4/c1-14-9-5-3-4-8(11(9)15-2)6-7-10(12)13/h3-7H,1-2H3,(H,12,13)/p-1/b7-6+

Upstream product

• 141-82-2 malonic acid 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 5424-52-2 (E)-4-(2,3-dimethoxyphenyl)-but-3-en-2-one 

Downstream Products

• 103796-18-5 2,3-dimethoxy-trans-cinnamic acid amide 
• 79618-90-9 (E)-ethyl 3-(2,3-dimethoxyphenyl)prop-2-enoate 
• 15854-60-1 methyl 3-(2,3-dimethoxyphenyl)propenoate 
• 1026126-04-4 (E)-N-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-(2,3-dimethoxy-phenyl)-acrylamide 
• 10538-48-4 2,3-dimethoxyhydrocinnamic acid 
• 1026259-26-6 1-((E)-7-Bromo-hept-3-enyl)-2,3-dimethoxy-benzene 
• 1026383-15-2 (E)-5-(2,3-Dimethoxy-phenyl)-pent-2-enoic acid ethyl ester 
• 1025893-47-3 Methanesulfonic acid (E)-5-(2,3-dimethoxy-phenyl)-pent-2-enyl ester 
• 1026822-94-5 (E)-7-(2,3-Dimethoxy-phenyl)-hept-4-enoic acid methyl ester 
• 1026289-23-5 Methanesulfonic acid (E)-7-(2,3-dimethoxy-phenyl)-hept-4-enyl ester 
• 1026306-70-6 2-[(E)-5-(2,3-Dimethoxy-phenyl)-pent-2-enyl]-malonic acid dimethyl ester 
• 103853-10-7 3-(2,3-dimethoxyphenyl)propan-1-ol 
• 129150-13-6 3-(2,3-Dimethoxy-phenyl)-propionaldehyde 
• 6342-80-9 4,5-dimethoxyindanone 

Relevant articles and documents

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Myeloid differentiation protein 2 (MD2) is an essential molecule which recognizes lipopolysaccharide (LPS), leading to initiation of inflammation through the activation of Toll-like receptor 4 (TLR4) signaling. Caffeic acid phenethyl ester (CAPE) from propolis of honeybee hives could interfere interactions between LPS and the TLR4/MD2 complex, and thereby has promising anti-inflammatory properties. In this study, we designed and synthesized 48 CAPE derivatives and evaluated their anti-inflammatory activities in mouse primary peritoneal macrophages (MPMs) activated by LPS. The most active compound, 10s, was found to bind with MD2 with high affinity, which prevented formation of the LPS/MD2/TLR4 complex. The binding mode of 10s revealed that the major interactions with MD2 were established via two key hydrogen bonds and hydrophobic interactions. Furthermore, 10s showed remarkable protective effects against LPS-caused ALI (acute lung injury) in vivo. Taken together, this work provides new lead structures and candidates as MD2 inhibitors for the development of anti-inflammatory drugs.

Copper catalyzed oxygen assisted C(CNOH)-C(alkyl) bond cleavage: A facile conversion of aryl/aralkyl/vinyl ketones to aromatic acids

A novel copper-catalyzed aerobic oxidative C(NOH)-C(alkyl) bond cleavage reaction of aryl/aralkyl/vinyl ketones for the synthesis of aromatic/acrylic acids is described. A series of ketones having aryl/aralkyl/vinyl at the one end and methyl to any higher alkyl at the other end can be selectively cleaved and converted into the corresponding acids via oxime intermediates.

Synthesis and leishmanicidal activity of cinnamic acid esters: Structure-activity relationship

Several cinnamic acid esters were obtained via Fischer esterification of cinnamic acids derivatives with aliphatic alcohols. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes and cytotoxic activity was evaluated against mammalian U-937 cells. The compounds 11, 15-17, and 23, were active against Leishmania parasite and although toxic for mammalian cells, they still are potential candidates for antileishmanial drug development. A SAR analysis indicates that first, while smaller alkyl chains lead to higher selectivity indices (10, 11 vs. 12-17); second, the degree of oxygenation is essential for activity, primarily in positions 3 and 4 (17 vs. 18-20 and 22); and third, hydroxyl groups increase both activity and cytotoxicity (14 vs. 23). On the other hand, the presence of a double bond in the side chain is crucial for cytotoxicity and leishmanicidal activity (12 vs. 21). However, further studies are required to optimize the structure of the promising molecules and to validate the in vitro activity against Leishmania demonstrated here with in vivo studies.

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Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium

The Rodionov reaction of 49 available aliphatic and aromatic aldehydes with malonic acid and ammonium acetate in alcoholic medium, resulting in formation of β-amino acids, propenoic, and ylidenemalonic acids, was studied. Certain regioselectivity regularities of the reaction were revealed. Among the variety of ketones studied, cyclohexanone is the only whose reaction yields a β-amino acid. Unusual dehydrofluorination of 6-chloro-2-fluorocinnamic acid under the Rodionov reaction was discovered. 2005 Pleiades Publishing, Inc.

Design and synthesis of low molecular weight compounds with complement inhibition activity

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This study was performed to explain a regiospecific demethylation of 3-alkyl-1,2-dimethoxybenzenes.PRDDO-MO calculations show that the low-energy conformation of the carbon of a methoxy group having two ortho neighbors on a benzene ring is located out of the plane of the aromatic ring, whereas a methoxy group with only one ortho neighbor executes restricted rotation in the plane of the ring.The carbon portion of the methoxy group is turned away from the neighboring substituent.These calculations also show that the atomic charge on the oxygen atom in the former caseexceeds that in the latter.The carbon of a methoxy group with two ortho neighbors yields 13C NMR T1 relaxation times longer than those with only one ortho neighbor, also suggesting that the methoxy group with two ortho neighbors is crowded out of the plane of the aromatic ring. 13C NMR chemical shifts of these ortho-substituted methoxybenzenes did not correlate well with shifts predicted from published additive parameters; this again suggests an unusual methoxy group orientation and distribution of electrons.The forced rotation of a methoxy group out of the plane of the benzene ring diminishes the release of electrons from the methoxy group to the benzene ring.The resulting higher atomic charge on the oxygen and the orientation of the oxygen orbitals facilitate complexation with Lewis acids and methoxy group cleavage.

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