This compound belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule building block. For chemical applications, refer to the Reaction Conditions and Synthetic Utility sections for representative procedures and conditions.
Biological Roles
Item-specific biological data: Not specified for this item; for research use only (per Product Data). No biological testing data are provided.
General context (literature):
Cinnamic acids are part of the broader phenylpropanoid family in plants, where analogous structures serve as intermediates in lignin, flavonoid, and coumarin biosynthesis. Methoxy substitution modulates lipophilicity and electronic properties, which can influence interactions with enzymes and membranes in biochemical assays.
The conjugated double bond and aromatic ring confer UV absorption typical of cinnamates; derivatives of cinnamic acid are widely used in research on antioxidant mechanisms, enzyme modulation, and as synthetic intermediates to probe structure–activity relationships. Such roles pertain to research contexts and do not imply any biological efficacy for this specific item.
Experimental considerations:
Solubility in aqueous buffers is limited unless converted to salts; DMSO stock solutions diluted into buffered systems are common in biochemical assays, maintaining final DMSO ≤1–2% v/v to minimize solvent effects.
The carboxylate’s pKa (~4.2–4.6, literature) means partial ionization occurs in mildly acidic media, which can alter partitioning and assay readouts.
Buffer Applications
This compound is not a buffering reagent and is not commonly used to prepare biological or analytical buffer systems.
Practical notes if used in buffered assays (general):
Prepare concentrated stocks in DMSO or ethanol, then dilute into the desired buffer while maintaining final organic cosolvent at low percentages.
Aqueous solubility increases in basic buffers (as carboxylate); if using as salt, adjust pH carefully and account for counterion effects.
For routine buffer preparation guidance, refer instead to dedicated buffering agents (e.g., phosphate, HEPES, Tris).
Green Alternatives
This product is a solid building block rather than a process solvent. “Green alternatives” thus focus on greener solvent and reagent choices when handling it.
Prefer bio-based or lower-toxicity solvents (EtOAc, MeTHF, 2-propanol, ethanol) over chlorinated solvents (DCM) or NMP/DMF when feasible.
For amidations/esterifications, use EtOAc or 2-MeTHF as medium; remove by reduced pressure with minimal energy.
For hydrogenation, ethanol is a practical green medium versus IPA/EtOAc blends.
Greener coupling strategies (general):
Employ water-compatible carbodiimides (EDC·HCl) or CDI in greener solvents; consider enzyme-catalyzed esterifications in green media for select applications.
Explore photoredox/nickel decarboxylative couplings in MeOH/EtOH/EtOAc rather than highly polar aprotics where compatible.
Tradeoffs:
Polar aprotic solvents (DMF/DMSO) enhance solubility and rates but introduce workup and environmental burdens; balance with substrate loading and temperature to enable greener alternatives.
Strong Lewis acids for O-demethylation (e.g., BBr3) are effective but hazardous; milder oxidative demethylations (e.g., using ceric ammonium nitrate on protected derivatives) may reduce hazards at the cost of selectivity.
Pharmaceutical Uses
Item-specific pharmacopeial status/uses: Not specified for this item; refer to CoA/Spec Sheet. This product is supplied strictly for research use only.
General formulation/manufacturing context (literature):
Aromatic cinnamic acid derivatives are used as intermediates in API synthesis and as reference compounds in analytical development. The trans-alkene and methoxy substitution provide handles for selective derivatization (esterification, amidation) to produce prodrugs or advanced intermediates.
In pre-formulation research, cinnamate scaffolds serve as chromophores for HPLC/UV method development and impurity profiling.
Excipient role: No recognized role as a standard excipient; not intended for human or veterinary administration.
Physical Properties
Item-specific specifications (from Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/typical values for the trans isomer (for reference; not item specifications):
Phase at ambient: organic solid (aromatic carboxylic acid)
Acid dissociation: pKa of cinnamic acids typically ~4.2–4.6 (literature); 2,3-dimethoxy substitution modestly acid-weakening relative to unsubstituted
Lipophilicity: clogP expected in the 1.3–1.8 range (prediction, literature/computed) due to two methoxy groups and one carboxylate
Solubility profile (qualitative, literature):
Water: low at neutral pH; increases markedly in basic media (as the carboxylate salt)
Organic solvents: soluble in polar aprotics (DMSO, DMF), moderately to well soluble in alcohols (MeOH/EtOH) and acetone/EtOAc; sparing in nonpolar hydrocarbons
UV/Vis: strong π→π* absorption in near-UV (conjugated cinnamate chromophore); specific λmax not provided here
Melting/boiling points, density, refractive index: Not specified here; consult primary literature or CoA/Spec Sheet for item-specific values.
Notes: All values above (except where marked as “Not specified”) are general literature/computed guidance for the class of compounds and the named structure and must not be treated as product specifications.
Quality & Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades for this material (general):
Research or analytical grades typically specify assay (e.g., HPLC/GC), residual solvents, and chromatographic purity. For conjugated aromatics, UV-Vis baselines and isomeric purity (E vs Z) can be relevant.
Isomeric composition: For cinnamic acid derivatives, the E (trans) isomer is usually predominant and often specified; verify by 1H NMR (coupling of vinyl protons, J ≈ 15–16 Hz for trans) and HPLC.
Common documentation: Certificate of Analysis (CoA) usually reports assay (%), identification (NMR/IR), loss on drying or KF (if applicable), and impurity profile.
Stabilizers: None are typically added for solid aromatic carboxylic acids; if any stabilizer is present, it should be declared on the label/CoA.
Practical recommendations:
If your application is photochemical or analytical, verify UV absorbance background and absence of colored impurities.
For synthesis, check for residual inorganic salts and confirm acid number or neutralization equivalent to ensure accurate stoichiometry.
Reaction & Applications
As a functionalized cinnamic acid, trans-2,3-dimethoxycinnamic acid serves as a versatile building block in synthesis and materials research.
Esterification: Fischer (acid-catalyzed in MeOH/EtOH) to give methyl/ethyl cinnamates; or DCC/EDC–DMAP mediated at rt in DCM/DMF.
Amidation: Carbodiimide (EDC/HOBt, HATU) coupling with amines to form amides; suitable in DMF/DCM with base (DIPEA).
Hydrogenation: Selective reduction of C=C (Pd/C, H2, EtOH) to the 2,3-dimethoxyphenylpropionic acid; harsher conditions reduce CO2H or O-demethylate (avoid).
Halogenation/activation of CO2H: Conversion to acid chloride (SOCl2 or oxalyl chloride, catalytic DMF) for acylation; subsequent reactions include Friedel–Crafts acylations of activated arenes.
Decarboxylative couplings: Via redox-active esters (NHP esters) enabling Ni/photoredox-mediated arylation, alkenylation, borylation—useful to access 2,3-dimethoxy-styrenyl derivatives.
O-Demethylation (if desired): BBr3/AlCl3 conditions to access catechol analogs (handle with care; the acid may require protection).
Perkin/Knoevenagel synthesis relevance: This molecule is a product-type of classic condensations; analogous methods are used for derivative preparation.
Practical tips:
Confirm E stereochemistry by 1H NMR (Jtrans ~15–16 Hz). Avoid prolonged strong acid/heat that can isomerize the double bond.
Methoxy groups direct electrophilic substitution ortho/para; however, the ring is already disubstituted—regioselectivity requires planning.
For coupling chemistry, dry solvents and exclude moisture; pre-form the acid chloride freshly to minimize polymerization/side reactions.
Reaction Conditions
Representative literature-type conditions for common transformations of this substrate (guidance only; optimize per lab):
Fischer esterification: ROH (MeOH/EtOH, 5–20 vol eq), catalytic H2SO4 or p-TsOH (1–5 mol%), reflux 4–16 h; remove water (Dean–Stark for higher alcohols). Typical isolated yields 70–95% depending on alcohol.
Steglich esterification: Alcohol (1.2–1.5 eq), DCC (1.2–1.5 eq), DMAP (0.1 eq), DCM (0.1–0.5 M), 0 °C to rt, 2–18 h; filter DCU; 70–95%.
Acid chloride formation: SOCl2 (3–5 eq), catalytic DMF (1–2 drops), reflux 1–3 h; remove excess under vacuum; use in situ. Alternatively, (COCl)2 under similar conditions.
Hydrogenation (C=C reduction): 5–10 wt% Pd/C (5–10 mol% metal), H2 (1–3 bar), EtOH or EtOAc, rt–40 °C, 2–8 h; monitor by TLC/HPLC; typical 80–95% to phenethyl acid.
Redox-active ester formation and decarboxylative coupling: N-hydroxyphthalimide (1.2 eq), DIC (1.2 eq), DMAP (0.1 eq), DCM, rt, 2–6 h to form RAEs; then Ni/photoredox catalysis (Ir(ppy)3 1–2 mol%, NiCl2·dme 5–10 mol%), blue LEDs, MeCN/MeOH/EtOAc, rt, 4–18 h (yields substrate- and partner-dependent).
Notes:
Protect methoxy groups if harsh Lewis acids/bases are employed.
Maintain anhydrous conditions for coupling; rigorously dry DCM/DMF and glassware.
Verify E/Z integrity post-reaction if exposure to strong acids/UV could isomerize the double bond.
Safety & Handling
GHS information from Product Data:
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General laboratory safety guidance for aromatic carboxylic acids (literature/best practice; defer to SDS):
Hazards: May cause skin/eye irritation and respiratory tract irritation as dust; avoid inhalation of particulates. Weak organic acids can cause localized irritation.
PPE: Use lab coat, suitable gloves (e.g., nitrile), safety glasses or goggles; handle powders in a fume hood to minimize dust exposure.
Handling: Avoid dust generation; use dedicated spatulas; cap containers promptly. For solutions, avoid contact with bases/acids that could cause exothermic neutralization.
Incompatibilities: Strong oxidizers; strong bases/acids (reactivity/neutralization); reagents that form reactive acid chlorides (e.g., SOCl2, oxalyl chloride) unless intended.
First aid (summary; follow SDS):
Skin/eye: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spills: Avoid dust; collect mechanically; wipe residue with damp disposable towels/appropriate solvent; dispose per regulations.
Fire: Combustible organic solid; use CO2, dry chemical, or foam. Combustion may produce CO/CO2; firefighters wear SCBA.
Always consult the product-specific SDS for definitive hazard classification and response procedures.
Solvent Selection
This product is a moderately lipophilic aromatic carboxylic acid with a conjugated alkene and two methoxy groups.
Polarity/miscibility (general, literature):
Poorly soluble in water at neutral pH; readily soluble as its carboxylate in aqueous base.
Good solubility in DMSO and DMF; moderate to good in methanol, ethanol, acetone, ethyl acetate; limited in nonpolar solvents (hexanes, toluene).
Selection guidance by task:
NMR: DMSO-d6 or CD3OD typically provide clear spectra; CDCl3 may require gentle warming/sonication due to limited solubility.
Purification: Recrystallization from alcohols (EtOH/MeOH) or EtOAc/hexanes mixtures is common; for base-labile impurities, use non-aqueous systems.
Reaction media: For esterification/amidation, use anhydrous DCM, DMF, or toluene with appropriate coupling agents; for hydrogenation, EtOH/EtOAc under H2 with Pd/C.
Aqueous workup: Adjust pH to 8–9 to extract as carboxylate into aqueous phase or to pH <2 to protonate and extract into organic phase.
Comparison (general):
DMSO vs DMF: DMSO offers higher solvating power and is greener but harder to remove; DMF is easier to remove but has regulatory scrutiny—choose based on downstream needs.
Alcohols vs esters: Alcohols can participate in Fischer esterification under acid; use esters (EtOAc) or chlorinated solvents (DCM) to avoid unintended ester formation.
Storage & Reconstitution
Storage (from Product Data):
Store at room temperature.
Shipped at ambient conditions (Normal).
General best practices for this compound class:
Keep tightly closed in a dry, well-ventilated place. Use desiccation if the laboratory environment is humid.
Protect from prolonged exposure to strong light/UV to minimize any risk of E/Z isomerization or discoloration of conjugated materials.
Avoid sources of strong acids/bases unless intended for reaction; the solid is generally stable under typical lab conditions.
Reconstitution/preparation of stock solutions (guidance):
DMSO stocks: 10–100 mM are readily prepared; filter-sterilize if needed for biochemical assays. Store aliquots at 2–8 °C or −20 °C to reduce freeze–thaw; warm to dissolve precipitates.
Alcoholic stocks: Prepare in ethanol or methanol for immediate use; verify stability if storing >24–48 h.
Aqueous use: Dissolve by adding a minimal amount of base (e.g., NaOH) to form the sodium salt, or cosolvate with DMSO before dilution into buffer; adjust pH after dilution as needed.
Research Use Note: For research use only (per Product Data).
Structure & Identity
trans-2,3-Dimethoxycinnamic acid is a cinnamic acid derivative bearing two adjacent methoxy substituents on the aromatic ring (ortho- and meta- to the styryl carboxylic acid side chain) and an E-configured (trans) double bond.
Item-specific identifiers from Product Data:
CAS: 7345-82-6
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists "292150", which is not a standard InChIKey format.)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and composition (for reference; not item-specific specifications):
Molecular formula (literature): C11H12O4
Molecular weight (literature): ~208.21 g/mol
Representative SMILES (literature): OC(=O)/C=C/c1c(OC)c(OC)ccc1 (depicts the E-alkene and 2,3-dimethoxy substitution)
Stereochemistry: E (trans) about the C=C bond of the cinnamate moiety
Functional groups: aromatic ring, two aryl methoxy (–OCH3) substituents at the 2- and 3-positions, α,β-unsaturated carboxylic acid (conjugated alkene + CO2H)
2D structure in words: a benzene ring bearing adjacent methoxy groups, para to which runs a trans-CH=CH–CO2H chain (conjugated to the ring).
Synthetic Utility
Key features of trans-2,3-dimethoxycinnamic acid that enable downstream synthesis:
Functional handles:
Carboxylic acid: convertible to esters, amides, acid chlorides, anhydrides; platform for coupling (EDC/HATU/CDI) and decarboxylative cross-couplings via redox-active esters.
Conjugated C=C: chemoselective hydrogenation (to phenethyl acid), Michael additions (with activated nucleophiles under specific conditions), and cycloadditions with strong dienophiles are possible though the electron-rich ring modulates reactivity.
Aryl methoxy groups: amenable to O-demethylation to catechols; direct metalation α to methoxy can be leveraged with directing strategies.
Retrosynthetic value:
Disconnection at the C=C bond suggests access via Perkin or Wittig/HWE olefination between a 2,3-dimethoxybenzaldehyde and an acetate/phosphonate equivalent to set the E geometry.
The acid can be protected (as ester) to enable conditions incompatible with CO2H (e.g., strong bases, Lewis acids) and later hydrolyzed.
Derivatization map (examples, literature):
Esters → photopolymerizable cinnamates or crosslinkable materials (research context).
Amides → conjugation to amines/peptides for probe development.
Decarboxylative borylation → 2,3-dimethoxy-styrenyl boronates for Suzuki couplings.
Target Specificity
Not applicable. This product is a small-molecule organic acid, not a biological targeting reagent (e.g., antibody, enzyme inhibitor with defined target panel). No target specificity data are provided in the Product Data.
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