Avenanthramide A - ≥99% , CAS No.108605-70-5

CAS: 108605-70-5 Cat. No.: A1048393 Numéro CE: 806-391-1 PubChem CID: 5281157

GRADE & PURITY ≥99%

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Specifications

Spécifications et pureté

≥99%

Conditions de stockage de stockage

Store at 2-8°C,Protected from light

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Pureté

≥99%

Noms et identifiants

• Sourires canoniques: C1=CC(=CC=C1C=CC(=O)NC2=C(C=C(C=C2)O)C(=O)O)O
• IUPAC Name: 5-hydroxy-2-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]benzoic acid
• InChIKey: QGUMNWHANDITDB-FPYGCLRLSA-N
• INCHI: 1S/C16H13NO5/c18-11-4-1-10(2-5-11)3-8-15(20)17-14-7-6-12(19)9-13(14)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-3+
• Isomères SMILES: C1=CC(=CC=C1/C=C/C(=O)NC2=C(C=C(C=C2)O)C(=O)O)O
• CAS alternatif: 108605-70-5
• PubChem CID: 5281157
• Termes d'entrée MeSH: avenanthramide A

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Cinnamic acids and derivatives
      • Subclass Hydroxycinnamic acids and derivatives
        • Level5 Hydroxycinnamic acids
          • Level6 Avenanthramides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Cinnamic acids and derivatives
• Subclass: Hydroxycinnamic acids and derivatives
• Intermediate Tree Nodes: Hydroxycinnamic acids
• Direct Parent: Avenanthramides
• Alternative Parents: N-cinnamoylanthranilic acids Acylaminobenzoic acid and derivatives Coumaric acids and derivatives Hydroxybenzoic acid derivatives Anilides Benzoic acids Styrenes Benzoyl derivatives N-arylamides 1-hydroxy-2-unsubstituted benzenoids Vinylogous amides Secondary carboxylic acid amides Carboxylic acids Monocarboxylic acids and derivatives Hydrocarbon derivatives Organopnictogen compounds Carbonyl compounds Organic oxides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Avenanthramide - N-cinnamoylanthranilic acid - Acylaminobenzoic acid or derivatives - Coumaric acid or derivatives - Cinnamic acid amide - Hydroxybenzoic acid - Benzoic acid or derivatives - Anilide - Benzoic acid - N-arylamide - Styrene - Benzoyl - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Benzenoid - Monocyclic benzene moiety - Vinylogous amide - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid.
• External Descriptors: hydroxycinnamic acid

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propriétés chimiques et physiques

• Poids moléculaire: 299.280 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 299.079 Da
• Monoisotopic Mass: 299.079 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 428.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

No item-specific, validated protocols are provided for this SKU. The following general procedures are commonly used when employing Avenanthramide A as an analytical standard or research probe; adjust to your system and validate internally.

• HPLC/LC–UV assay (general):

  • Prepare a 10 mM stock in DMSO. Dilute into 50:50 MeOH/H2O (0.1% formic acid) to 1–100 µM calibration standards.
  • Column: C18 reversed phase; mobile phase: water (0.1% acid) / acetonitrile or methanol gradient; detect at dual wavelengths (e.g., 280 and ~320 nm) to capture aromatic and cinnamoyl chromophores.

• LC–MS setup (general):

  • Ionization: ESI negative mode commonly gives strong deprotonated [M–H]− signals for phenolic acids/amides; scan for m/z ~298 (literature MW 299.28).
  • Keep DMSO ≤1% in final injections to avoid ion suppression.

• Photostability test (general):

  • Split solutions into amber vs clear vials; expose clear vials to ambient light; monitor E/Z ratio and degradation by HPLC over time.

• Antioxidant assay controls (chemical, not biological claims):

  • Include Avenanthramide A as a comparator in in vitro radical scavenging assays (e.g., DPPH) with Trolox standards.

These are general/literature-style methods. Item-specific performance characteristics are Not specified for this item; refer to CoA/Spec Sheet and SDS.

Biological Roles

General/literature perspective (no clinical claims):

• Natural occurrence: Avenanthramide A is a predominant phenylpropanoid amide in oats (Avena sativa). It consists of p-coumaric acid coupled via an amide bond to 5-hydroxyanthranilic acid. It belongs to the avenanthramide family (A, B, C) that vary by substitution on the cinnamoyl ring.

• Biosynthesis (plant biochemistry): Formed via the phenylpropanoid pathway and arylamine N-acyltransferases that couple hydroxycinnamoyl-CoA thioesters to hydroxyanthranilic acid. The trans cinnamoyl double bond is typical in the native metabolite.

• Biochemical properties: The conjugated system and phenolic groups support radical stabilization and metal-chelation behaviors; these underlie common observations of antioxidant capacity in chemical assays (e.g., DPPH, ABTS, ORAC) in vitro. Such assay activities are context-dependent and do not imply physiological effects.

• Plant role: Reported to participate in defense-related responses and stress signaling in oats, consistent with phenylpropanoid amide functions in plants (literature).

• Analytical relevance: Serves as a marker compound for authenticity and quality assessment of oat-derived materials and for comparative metabolomics across cultivars and processing conditions.

Note: The above are literature/general insights and are not specifications or performance guarantees for this specific item. For research use only.

Buffer Applications

This compound is not a buffering reagent. However, it can be used in buffers as an analyte or assay probe.

• Compatibility (general guidance):

  • Prepare concentrated stocks in DMSO, then dilute into the desired assay buffer (e.g., phosphate, HEPES) while keeping final DMSO ≤1–2% v/v to minimize solvent effects.
  • Aqueous solubility improves at basic pH due to carboxylate formation; however, sustained alkaline pH may promote slow amide hydrolysis and E/Z isomerization. For stability, use near-neutral pH (6.5–7.5) when feasible and minimize light exposure.

• Adsorption considerations: Phenolic aromatics may adsorb to plastics at low concentrations; prefer glass vials and silanized glass LC vials for trace work.

• Filtration: Use low-binding PTFE or PVDF syringe filters; avoid nylon for acidic solutions due to potential interaction with phenolics.

• Example preparation (general, not item-specific):

  • 10 mM stock in DMSO → dilute 1:1000 into 50 mM phosphate buffer, pH 7.4, to achieve 10 µM working solution (final DMSO 0.1%). Verify solubility visually and by baseline stability in UV.

Item-specific buffer capacities, pKa values, and ionic strength effects are Not specified for this item; consult primary literature and validate in your system.

Green Alternatives

While Avenanthramide A itself is a target analyte rather than a solvent/reagent, greener choices can be made in its handling, extraction, and analysis.

• Greener solvent choices (general):

  • Prefer bio-ethanol or water–ethanol mixtures for sample preparation and solid-phase extraction loading/wash steps when matrix allows.
  • Replace chloroform/DMF where possible with ethyl acetate, MeTHF, or aqueous MeOH/ACN for partitioning and chromatography.

• Minimizing environmental footprint:

  • Use aqueous LC with higher water fractions and shorter gradients; optimize column efficiency to reduce solvent consumption.
  • Employ UHPLC to cut run times and solvent volumes.
  • For solid-phase cleanup, select reusable glassware and low-waste SPE formats (e.g., microcartridges) and recover solvents for recycling when compliant.

• Trade-offs (balanced view):

  • Ethanol/water improves safety but may reduce extraction efficiency for tightly bound phenolics compared to MeOH/acetone.
  • 2-MeTHF is bio-based and less volatile than THF but can give different selectivity in normal-phase separations; confirm method suitability.

Comparison snapshot (general guidance):

• Ethanol/H2O: safer, renewable; moderate extraction strength; excellent for food matrices.
• MeOH: strong extractor; toxic; good UV transparency.
• ACN: superior LC performance; petrochemical origin; moderate toxicity.

Note: No item-specific green certifications apply; implement lab-level green chemistry practices aligned with your method constraints.

Pharmaceutical Uses

No pharmacopeial grade or excipient status is provided for this item. This product is supplied strictly for research use.

• Formulation context (general): Avenanthramide A may be employed as a reference marker in quality control of botanical raw materials or experimental formulations containing oat-derived phenolics. It can assist in identity testing, content uniformity studies, and stability-indicating method development.

• Analytical roles:

  • System suitability/retention marker in HPLC methods for phenylpropanoid amides.
  • Reference standard for calibration curves in LC–UV/LC–MS.

• Not a drug substance/excipient: There is no claim of compliance with USP/Ph.Eur./JP monographs for this specific lot. Any use in regulated development would require independent qualification and fit-for-purpose validation by the user.

• Stability-indicating studies (general): Useful for forced-degradation panels (light, oxidative, thermal, pH stress) to challenge analytical methods intended for oat or phenolic-containing formulations.

Item-specific regulatory status, residual solvent limits, and elemental impurity profiles: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Item-specific specifications have not been provided for this SKU. Where helpful, representative literature values are included strictly for contextual use in method development; verify against the CoA/SDS before use.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (literature): ~299.28 g/mol (C16H13NO5).
• Acid–base character (literature): weakly acidic (carboxylic acid, phenolic OH); amide is neutral; no formal basic center.
• Solubility (literature/experience):
  • Good solubility in polar aprotic organics (DMSO, DMF, NMP); soluble in methanol/ethanol; sparingly soluble in water at neutral pH; increased aqueous solubility in basic media via carboxylate formation (note: base may promote E/Z isomerization and slow hydrolysis over time).
• UV/Vis (literature): strong π–π* absorption in near-UV due to cinnamoyl conjugation; typical λmax reported in the 300–330 nm range with additional band ~280 nm; exact cutoff/ε Not specified for this item; refer to CoA/Spec Sheet.
• LogP/logD (literature): moderate hydrophobicity (aromatic–amide conjugate); reported logP values in the low-to-mid 1–2 range depending on method; item-specific value Not specified.
• Melting point, refractive index, density, water or peroxide content: Not specified for this item; refer to CoA/Spec Sheet.

Stability considerations (literature): photosensitive (cinnamoyl E→Z isomerization and oxidation possible); phenolic oxidation in air/light may occur—protect from light and store cool as per Product Data.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet. In the absence of a declared grade, users should confirm assay, residual solvents, and chromatographic purity by reviewing the CoA and, if needed, running orthogonal purity checks (e.g., HPLC-UV with dual wavelengths, LC–MS, and 1H NMR).

• Typical quality considerations for Avenanthramide A standards:

  • Isomeric integrity: E/Z ratio of the cinnamoyl double bond can shift under light/alkaline conditions; high-quality material will specify E:Z content or confirm E-isomer predominance.
  • Oxidative by-products: Phenoxy radical coupling or quinone-like species can form on prolonged exposure; look for low-level late-eluting peaks in HPLC.
  • Water content: Hygroscopicity is generally low-to-moderate, but Karl Fischer values may be reported; for this item: Not specified for this item; refer to CoA/Spec Sheet.
  • Residual metals/peroxides/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• Stabilizers: None stated for this item. If present in other lots, stabilizers (e.g., antioxidants) can impact UV/Vis and redox assays—verify prior to analytical use.

• Documentation: Request CoA, NMR, and chromatograms for the specific lot received. For quantitative studies (e.g., calibration standards), consider secondary verification against a certified reference material when available.

Reaction and Applications

This compound is primarily used as a reference standard and probe molecule in natural products, redox chemistry, and plant metabolite studies, rather than as a routine reagent. Nevertheless, its conjugated phenylpropanoid amide scaffold lends itself to several practical applications.

• Research applications (general/literature):

  • Analytical standard for oat-derived avenanthramides in food/plant matrices (HPLC/LC–MS method development, retention/response factor benchmarking).
  • Model substrate for studying phenolic oxidation, radical scavenging kinetics, and E/Z photoisomerization of cinnamoyl systems.
  • SAR comparisons among Avenanthramides A, B, and C (p-coumaroyl vs feruloyl vs caffeoyl substitutions) in biochemical assays.

• Chemical reactivity/transformations (literature):

  • Esterification of the carboxylic acid to form methyl/ethyl esters for volatility and stability in GC/MS or to tune lipophilicity.
  • Selective protection of phenolic OH groups (e.g., acetates, benzyl ethers) to modulate stability and chromatographic behavior.
  • Amide hydrolysis (harsh) to regenerate 5-hydroxyanthranilic acid and p-coumaric acid; base- or enzyme-catalyzed routes studied mechanistically.
  • Photoinduced E↔Z isomerization about the cinnamoyl double bond; monitor by UV and HPLC.

• Practical tips:

  • Protect from light during experiments; use amber vials and wrap glassware with foil.
  • Degas solutions for oxidation studies; add internal standards for quantitative work.
  • Calibrate detection at two wavelengths (e.g., 280 and ~320 nm) to follow aromatic and cinnamoyl chromophores, respectively.

Reaction Conditions

General literature conditions related to synthesis/derivatization of Avenanthramide A (for context; not item specifications):

• Amide bond formation (EDC/HOBt):

  • Reagents: 1.1–1.5 equiv EDC·HCl, 1.1 equiv HOBt (or Oxyma), base (DIPEA), p-coumaric acid, 5-hydroxyanthranilic acid.
  • Solvent: DMF or DCM/DMF; 0–25°C; 4–18 h.
  • Notes: Protect phenols if competitive O-acylation occurs; exclude light to preserve E-isomer; typical isolated yields reported in moderate-to-good range depending on protection strategy (literature).

• Acid chloride coupling:

  • Generate p-coumaroyl chloride with oxalyl chloride (cat. DMF), then couple to anthranilate in pyridine or DCM with base at 0–5°C to RT.
  • Caution: acid chlorides can racemize adjacent stereocenters in other systems and may cause E→Z isomerization; use low temperatures and short times.

• Esterification (Fischer):

  • MeOH, catalytic H2SO4 or HCl(g), RT–reflux; monitor to avoid amide cleavage.

• Photochemistry:

  • E↔Z isomerization under UV/visible irradiation; monitor by HPLC-UV at dual wavelengths (e.g., 280/320 nm). Work under amber light to maintain isomer ratio.

• Oxidation studies:

  • Phenoxyl radical generation with peroxidase/H2O2 or electrochemical methods to assess redox behavior; degas and use scavengers as controls.

All parameters above are literature/general guidance and must be optimized per laboratory conditions.

Safety and Handling

• Regulatory/SDS note: Definitive hazard classification and exposure controls must be taken from the product SDS. The following are general laboratory precautions for phenolic amide natural products.

• GHS classification and hazard statements: Not specified for this item; refer to SDS. In absence of classification, handle as a Combustible Solid, Harmful if swallowed/inhaled/absorbed, Eye/Skin Irritant (general precautionary approach).

• Primary hazards (general):

  • Phenolic functionality may cause skin/eye irritation; dusts may irritate respiratory tract.
  • Conjugated phenolics can be light-sensitive; degradation may generate additional irritants.

• PPE and engineering controls:

  • Wear lab coat, nitrile gloves, and splash goggles; handle powders/solutions in a fume hood to minimize inhalation.
  • Avoid direct light during handling; use amber glassware when feasible.

• Incompatibilities (general):

  • Strong oxidizers; strong bases/acids (can promote hydrolysis/isomerization); prolonged exposure to UV/visible light.

• First aid overview (consult SDS for detailed steps):

  • Skin: Wash with soap/water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; obtain medical advice.

• Fire response: Use CO2, dry chemical, or foam; combustion may produce CO/CO2 and nitrogen oxides.

• Waste: Collect solutions/solids as organic chemical waste per institutional and local regulations.

Solvent Selection

Avenanthramide A is a moderately polar, polyphenolic amide with limited aqueous solubility at neutral pH but good solubility in polar organics.

• Practical solvent choices (literature/practice):

  • Stock preparation: DMSO (preferred), DMF, or NMP for high-concentration stocks; methanol or ethanol for HPLC calibration standards.
  • Working solutions: Dilute DMSO stocks into aqueous buffers; maintain final organic ≤1–2% v/v for most biochemical assays to avoid solvent effects.
  • Aqueous solubilization: Brief basification (e.g., dilute NaOH) can form the carboxylate to increase solubility; promptly neutralize to minimize amide hydrolysis and E/Z isomerization.

• Polarity/miscibility (general):

  • Polar aprotic solvent compatibility is excellent; miscible cosolvent systems (MeOH/H2O, ACN/H2O) are commonly used for LC.

• When to choose alternatives:

  • If phenolic oxidation is a concern, prefer oxygen-free, degassed solvents and amber vials.
  • For greener practice, consider bio-based ethanol or 2-MeTHF for extractions; for analytical LC, aqueous ACN or MeOH remain standards.

• Small comparison (general):

  • DMSO: maximal solubility, strong UV background >260 nm.
  • MeOH: good for UV at ~320 nm; volatile and LC-friendly.
  • ACN: lower viscosity, good peak shape; moderate solubility vs MeOH.

Note: Item-specific solvent specifications (water solubility, partition coefficients, UV cutoff) are Not specified for this item; refer to CoA/Spec Sheet.

Storage and Reconstitution

• Storage conditions (from Product Data): Store at 2–8°C, protected from light. Shipments are on wet ice.

• Light/oxygen precautions: Use amber vials or wrap in aluminum foil to minimize E→Z isomerization and oxidative degradation. For long-term retention of potency and chromatographic purity, minimize headspace oxygen and consider inert gas overlay (N2/Ar) after opening.

• Reconstitution (general guidance):

  • Solvents: DMSO (preferred), DMF, or ethanol; aqueous buffers are suitable only after preparing an organic stock solution.
  • Suggested stock: 10–50 mM in DMSO, aliquoted into light-protected microvials. Label with preparation date and concentration.
  • Filtering: If particulate is observed, clarify with a 0.2 µm PTFE filter.

• Aliquoting and freeze–thaw: To avoid concentration drift and degradation, prepare single-use aliquots. If freezing solutions, store at ≤−20°C in amber vials and avoid repeated freeze–thaw cycles.

• Stability notes (general/literature): Phenolic amides can slowly degrade under light, heat, and alkaline pH; monitor by HPLC. Maintain neutral pH in aqueous media when possible and use fresh dilutions.

• Container compatibility: Prefer glass. For low-concentration aqueous work, use low-bind/silanized glass to limit adsorption.

Item-specific shelf life, assay limits, and impurity specifications: Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

Avenanthramide A is a phenylpropanoid amide (oat-derived avenanthramide) comprising a p-coumaroyl moiety conjugated to 5-hydroxyanthranilic acid via an amide linkage.

• Item-specific identifiers (from Product Data):

  • SKU: A1048393
  • Product Name: Avenanthramide A
  • CAS: 108605-70-5
  • PubChem CID: 5281157
  • InChIKey: 296551 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structure description (general/literature):

  • Core features: trans-cinnamoyl (p-coumaroyl; 4-hydroxycinnamoyl) fragment conjugated to an anthranilic acid ring bearing a phenolic OH at the 5-position; amide bond at the 2-amino (ortho to carboxyl) position of anthranilic acid.
  • Functional groups: phenolic hydroxyls (2 total), amide, carboxylic acid (on the anthranilate), conjugated alkene (E-cinnamoyl), and two aromatic rings.
  • Stereochemistry: E (trans) about the cinnamoyl C=C (literature/common form).

• Empirical identifiers (literature, for reference only; not item specifications):

  • Molecular formula (literature): C16H13NO5
  • Molecular weight (literature): ~299.28 g/mol

• 2D depiction in words: an anthranilic acid ring bearing CO2H at C1, amide at C2 linking to a para-hydroxycinnamoyl chain terminating in a phenyl ring with a p-OH; an additional phenolic OH at C5 of the anthranilic ring; the cinnamoyl double bond is conjugated to the aryl ring and the amide carbonyl.

Synthetic Utility

Although Avenanthramide A is typically a target/analyte rather than a synthon, its functionality provides instructive chemistry and potential derivatizations.

• Functional group handles:

  • Carboxylic acid (anthranilate): amenable to esterification (MeOH/HCl, Fischer) or coupling to form amides/anhydrides.
  • Phenolic OH groups: protectable as acetates, carbonates, or benzyl ethers; sites for selective O-alkylation/acylation.
  • Amide bond: stable under mild conditions; hydrolyzable under strong acid/base or enzymatic amidase conditions (mechanistic studies).
  • Conjugated alkene: undergoes E↔Z photoisomerization; potential for Michael-type additions under specific activation, though deactivated by conjugation to amide and aryl ring.

• Named methods relevant to preparation/derivatization (literature):

  • Carbodiimide couplings (DCC or EDC·HCl) with catalytic DMAP/HOBt to assemble the amide from p-coumaric acid (or its activated ester) and 5-hydroxyanthranilic acid.
  • Acid chloride route: p-coumaroyl chloride generated with oxalyl chloride and coupled to anthranilate under basic conditions at low temperature.
  • Transesterification/esterification to modulate lipophilicity for analytical separations.

• Retrosynthetic note: Disconnection at the amide reveals hydroxycinnamic acid (p-coumaric) and 5-hydroxyanthranilic acid building blocks; protecting-group strategy typically required to control O- vs N-acylation.

These points are literature/general; they are not manufacturing instructions for this item.

Target Specificity

Not applicable. This product is a small-molecule phenylpropanoid amide, not an antibody or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.