Aciculatin , CAS No.134044-97-6

CAS: 134044-97-6 Cat. No.: A1445246 Formula: C₂₂H₂₂O₈ Molecular Weight: 414.41

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Aciculatin is a compound with cytotoxic, anti-inflammatory and anti-arthritic activities, and its synthetic route including specific chemical reaction steps was determined through the first total synthesis.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

Molecular Weight

414.41

Application Protocols

No manufacturer-validated application protocols are provided for this item. The following are literature-style, non-product-specific examples to help design experiments. Verify and optimize for your system.

• LC‑MS/MS calibration (example, literature/general):
  1. Prepare a 10 mM stock in DMSO (amber vial). 2) Serially dilute into MeOH to 1.0 mg/mL, then into 50:50 MeOH:water (0.1% formic acid) to 1–1000 ng/mL. 3) Inject 2–10 μL on a C18 column (e.g., 2.1×100 mm, 1.7 μm). 4) Gradient 5–95% ACN over 10–15 min. 5) Monitor UV 340 nm and MS MRM transitions optimized for your instrument. 6) Assess linearity (R2≥0.995), LOD/LOQ, and matrix effects via post-extraction spike.
• In vitro assay dosing (general):
  1. Make 50 mM DMSO stock. 2) Dilute into assay buffer to desired μM concentration ensuring final DMSO ≤0.1–0.5%. 3) Include vehicle controls and adsorption controls (low-bind plastics/glass). 4) Confirm absence of precipitation by light scattering or visual check.
• Stability check by HPLC (general):
  1. Store aliquots at −20 °C. 2) At defined intervals, thaw one aliquot, analyze by short C18 method. 3) Compare area% of the main peak to baseline; investigate new peaks for oxidative/deglycosylated products. These are illustrative only and not validated for this specific lot. Consult the CoA for lot-specific guidance.

Biological Roles

• Context (literature/general): Aciculatin is described as a plant-derived flavone C‑glycoside. Flavonoid glycosides serve as secondary metabolites involved in plant defense, UV protection, pigmentation, and signaling. C‑glycosides are notably more resistant to hydrolysis than O‑glycosides due to the C–C glycosidic bond.
• Molecular features relevant to biology:
  • Multiple phenolic hydroxyl groups enable hydrogen bonding and metal chelation; these features can modulate interactions with proteins and membranes in experimental systems.
  • The sugar moiety increases polarity and can influence transport/uptake in plant tissues and, in in vitro systems, modulate permeability compared to the corresponding aglycone.
• Research use (non-clinical):
  • Employed as a defined standard to study biosynthetic pathways of flavonoid C‑glycosides in plants via metabolomics and stable isotope labeling.
  • Used as a calibration/analyte for assessing extraction efficiencies from botanical matrices and for profiling stress-induced metabolic changes.
• Important caveats:
  • Any biological activity observations in literature are system- and assay-dependent and should not be extrapolated to clinical contexts; this product is for research use only.
  • Binding of polyphenols to assay components (e.g., serum proteins, plastic surfaces) can complicate interpretation; include appropriate vehicle and matrix controls.

Buffer Applications

This compound is not a buffering agent. However, it is frequently dissolved into assay buffers for in vitro research.

• Preparation for aqueous assays (general guidance):
  • Prepare a concentrated stock (e.g., 10–50 mM) in DMSO under low light. Vortex and, if needed, gently warm (≤35 °C) to aid dissolution; avoid prolonged heating.
  • Dilute into pre-warmed assay buffer with vigorous mixing to achieve final DMSO ≤0.1–0.5% v/v. Common buffers: PBS, HEPES, or Tris; select based on downstream assay compatibility.
  • Filter through 0.22 μm PTFE (preferred) or PES if particulate persists; avoid cellulose filters that may adsorb polyphenols.
• Practical considerations:
  • Phenolic compounds can exhibit pH-dependent ionization; verify pH after addition of stock solution if precise pH is critical.
  • Adsorptive losses to plastics may occur at sub‑μM levels; use low-bind plastics or glass vials/cuvettes.
• Stability checks:
  • Track UV‑Vis or HPLC peak area over time in your working buffer to confirm short-term stability and absence of precipitation.
  • If instability is observed, consider adding an inert protein carrier (e.g., 0.1% BSA) or 0.01–0.05% antioxidant compatible with the assay—validate to avoid interference.

Green Alternatives

As a solid natural product reference compound, “green alternatives” primarily concern the choice of solvents and workflows rather than replacement of the molecule itself.

• Solvent considerations (general):
  • Prefer ethanol/water mixtures where feasible for preparative handling; however, analytical solubility/response may necessitate MeOH or ACN.
  • Choose ACN over MeOH when reduced toxicity and improved biodegradability tradeoffs fit your method goals; consider recycled/LC‑MS‑grade solvents with on-site purification.
• Workflow optimization:
  • Minimize DMSO usage by preparing higher-concentration stocks and performing accurate micro-dilutions.
  • Implement microplate-based assays and microscale extractions (SPE) to reduce solvent volume.
• Comparison (general guidance): | Use-case | Conventional choice | Greener shift | Trade-offs | | — | — | — | — | | LC‑MS calibration | ACN/0.1% FA | EtOH/water (if soluble) or ACN recovered via solvent recycler | Solubility/peak shape may suffer in EtOH; recycling requires infrastructure | | Sample prep | Liquid–liquid with CH2Cl2/EtOAc | EtOAc or 2‑MeTHF; or SPE with aqueous elution where possible | Recovery for polar glycosides may drop; method re-validation needed |
• Energy and materials:
  • Use amber glass vials and maintain cold-chain storage to slow degradation, reducing the need for repeat syntheses/purchases.
  • Batch your analytical runs to limit purge/vent cycles and solvent consumption.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. This product is supplied strictly for research use only and is not intended for human or veterinary use.

• Relevant non-clinical/analytical contexts (general):
  • Reference standard in quality assessment of botanical raw materials or extracts that are known to contain aciculatin or related flavonoid C‑glycosides.
  • System suitability marker and retention-time/fragmentation check compound for LC‑UV/LC‑MS profiling of polyphenolic fractions.
  • Tool compound in pre-formulation research exploring solubility enhancement strategies (co-solvents, cyclodextrins) for polyphenolic analytes.
• Manufacturing/QA notes (general):
  • When used as a calibrant in process development or botanical QC, document purity, lot-specific assay values, and exact solvent composition of standards (especially water content) to ensure traceability.
  • Employ stability-indicating methods to differentiate degradation products (e.g., oxidative dimers or de‑glycosylated species) from the parent during storage studies of botanical materials.
• Regulatory disclaimer: No compendial monograph is cited here; any use in regulated workflows should be supported by internal method validation and reference to the item’s CoA and SDS.

Physical Properties

Item-specific physico-chemical specifications were not provided in the Product Data; consult the CoA/Spec Sheet for definitive values.

• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Literature for flavone C‑glycosides often shows decomposition or broad melting ranges.)
• Boiling point: Not applicable/Not meaningful (decomposes before boiling; literature generalization for glycosylated polyphenolics).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable to solids; Not specified for this item; refer to CoA/Spec Sheet.
• pKa: Not specified for this item; literature for phenolic flavonoids often shows multiple acidic pKa values (>7 for less activated phenols; lower if conjugated/chelating). Use experimental determination for this item if critical.
• LogP/LogD: Not specified for this item; literature expectation for glycosides is lower logP (greater polarity) than the corresponding aglycone.
• Solubility (literature/general guidance):
  • Highly soluble in DMSO; soluble in methanol and acetonitrile; sparingly to moderately soluble in ethanol; poorly soluble in water at neutral pH due to the flavone core despite the sugar.
  • Aqueous solubility can improve with co-solvent (e.g., 0.1–1% DMSO) or mild basification, but base can risk phenolate formation and potential degradation—evaluate stability before use.
• UV/Vis (literature/general for flavones): strong π–π* bands near 250–280 nm and 330–360 nm; exact λmax depends on substitution and medium. Use your own spectrum for method development.

Quality & Grades

• Grade/purity in Product Data: Not specified for this item; refer to CoA/Spec Sheet.
• Typical expectations for research-grade natural product reference standards (general/literature):
  • High chemical purity by HPLC/UPLC (often ≥95%) and defined identity by NMR/MS/UV are customary for quantitative work. When performing quantitative LC‑MS, verify residual solvent levels and moisture content if relevant to assay accuracy.
• What the grade implies (general):
  • Analytical/reference grade: tight control of chromatographic purity and UV background for quantification and method validation.
  • Standard research grade: suitable for screening, mechanistic assays, or as a spike/recovery control; may carry broader impurity profiles.
• Stabilizers: None specified for this item. If stabilizers/antioxidants are required in your workflow, select them to be LC‑MS compatible (e.g., ascorbate/metabisulfite used cautiously). Always confirm absence/presence on the CoA if stabilizers could interfere with analytical endpoints.
• Recommended verification at receipt:
  • Inspect CoA for identity (NMR, HRMS, UV), chromatographic purity, and water content if gravimetric standard preparation is planned.
  • Run a quick HPLC purity check under your method to ensure baseline separation of potential congeners common to plant extracts.

Reaction & Applications

Given its role as a complex natural product standard, aciculatin is more commonly used as an analytical reference and probe rather than as a bulk reagent in synthetic transformations.

• Research/analytical applications (literature/general):
  • Reference standard for quantification of aciculatin in plant materials by HPLC‑UV or LC‑MS/MS (calibration curves, spike–recovery, matrix validation).
  • Positive control in phenolic/flavonoid content assays; method development for separation of C‑ vs O‑glycosides.
  • Tool compound in chemical biology screens to study interactions of polyphenolic scaffolds with enzymes or transporters (non-clinical, research only).
• Derivatization possibilities (method development):
  • Phenolic groups can be methylated (e.g., MeI/K2CO3 or diazomethane—exercise extreme caution) to assess peak identity/shift or improve GC amenability.
  • Acetylation (Ac2O/pyridine) of hydroxyls provides diagnostic mass shifts for structure confirmation.
• Practical tips:
  • Dry, oxygen-reduced conditions extend solution stability; consider preparing fresh standards every 1–2 weeks and storing aliquots at −20 °C.
  • For LC‑MS/MS, optimize collision energies to track both aglycone and sugar-involving fragments typical of C‑glycosides.
• Not typically used in: organometallic catalysis, cross-coupling, or as a solvent/reductant; instead, refer to Synthetic Utility for its relevance as a structural benchmark.

Reaction Conditions

There are no item-specific reaction condition specifications for this product. The compound is generally employed as an analytical standard or probe rather than as a reagent. The following guidance is general/literature-based for handling and derivatization relevant to method development:

• Methylation of phenolic –OH (for GC amenability/peak ID):
  • Diazomethane in ether at 0–25 °C, minutes to hours; or MeI/K2CO3 in acetone/DMF at room temperature to 50 °C, 1–4 h. Strict safety protocols required for diazomethane.
• Acetylation (for MS shift/confirm –OH count):
  • Ac2O/pyridine or DMAP catalysis in DCM/MeCN, 0–25 °C, 0.5–2 h. Quench with MeOH/water and purify rapidly to avoid hydrolysis.
• Stability considerations:
  • Avoid strong base (>pH 10) and prolonged heating, which can induce degradation or rearrangements of polyphenolic glycosides.
  • Minimize exposure to air and light; perform under nitrogen/argon when feasible.
• Analytical method development (LC‑MS/MS; literature general):
  • Mobile phase: water/ACN or water/MeOH with 0.05–0.1% formic acid; gradient elution.
  • Detection: ESI negative and positive modes can both be informative; optimize source temperature and cone voltage for maximal response. Note: The above are general literature conditions for phenolic flavonoids/C‑glycosides and are not specifications for this item. Verify on small scale before adoption.

Safety & Handling

• GHS classification and hazard statements: Not specified for this item; refer to SDS.
• Signal word/pictograms: Not specified for this item; refer to SDS.
• General laboratory precautions (good practice for polyphenolic natural products):
  • Wear appropriate PPE: lab coat, safety glasses, and nitrile gloves. Avoid inhalation of dust and contact with skin/eyes.
  • Handle powders in a fume hood to minimize dust exposure. Use anti-static tools/spatulas for accurate weighing of small quantities.
  • Avoid strong bases, strong acids, and strong oxidants; phenolic natural products can undergo oxidation or hydrolysis under harsh conditions.
  • Protect from light to minimize photo-oxidation; use amber vials and foil wrapping during handling and storage.
• First-aid overview (defer to SDS for authoritative instructions):
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; monitor for respiratory irritation; seek medical advice if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Collect in organic solid/solution waste per institutional and local regulations. Avoid drain disposal.
• Special risks: Phenolic compounds may bind to plastics; prefer glassware for analytical standards. Trace metal ions can catalyze oxidation—use high-purity solvents and, if needed, add chelators or degas solutions.

Solvent Selection

• Polarity class and miscibility (literature/general for flavone glycosides):
  • Best primary solvents: DMSO (excellent), methanol (good), acetonitrile (good). Ethanol: moderate. Water: typically low solubility without co-solvent.
  • For LC‑UV/LC‑MS, acetonitrile/water or methanol/water with 0.1% formic acid are common mobile phases; formic acid can sharpen peaks and improve ionization.
• Choosing solvents by use-case:
  • Stock solutions for bioassays: prepare at 10–50 mM in anhydrous DMSO; dilute into aqueous buffers to ≤0.1–0.5% DMSO final to minimize vehicle effects.
  • Analytical calibration: prepare gravimetric standards in methanol or acetonitrile for HPLC/UPLC; use class-A glassware and verify solution stability.
  • Spectroscopy: methanol or acetonitrile in amber cuvettes to minimize photodegradation.
• Practical tips:
  • Degas solutions (sparging or sonication under inert gas) to limit oxidative degradation of phenolic moieties.
  • Glass vials with PTFE-lined caps reduce adsorption losses compared to polypropylene at low μg/mL levels.
• Quick comparison (general):
  • DMSO: maximal solubility; may suppress ESI response at higher %; viscous.
  • MeOH: LC‑MS friendly, protic; can promote acyl/ketal exchange in sensitive compounds—evaluate stability.
  • ACN: LC‑MS friendly, aprotic; lower viscosity; sometimes lower solubility than MeOH for glycosides.

Storage & Reconstitution

• Storage conditions (from Product Data): Store at −20 °C. Protect from light. Maintain desiccation if possible to limit moisture uptake. Do not store in frost-prone auto‑defrost freezers due to temperature cycling.
• Shipping: Shipped in an ice chest with ice pads (from Product Data) to preserve integrity during transit.
• Reconstitution (general guidance for polyphenolic glycosides):
  • Allow vial to equilibrate to room temperature in a desiccator before opening to prevent condensation.
  • For analytical stocks, dissolve in anhydrous DMSO (preferred for maximum solubility) or LC‑MS–grade methanol/acetonitrile. Typical stock concentrations: 10–50 mM (verify solubility empirically).
  • Vortex thoroughly; brief sonication may help. Avoid prolonged heating; if needed, gentle warming (≤35 °C) can aid dissolution.
• Aliquoting and stability:
  • Prepare single-use aliquots in amber glass vials; flush headspace with inert gas (N2/Ar) if long-term storage is planned.
  • Store aliquots at −20 °C. Minimize freeze–thaw cycles; discard aliquots showing discoloration or new peaks by HPLC.
• Aqueous working solutions:
  • Prepare fresh on the day of use. If stability beyond 24 h is required, verify by a stability-indicating HPLC method at your working concentration and matrix.
• Item-specific specifications not provided:
  • Moisture limits, assay/purity, residual solvents, and exact solubility: Not specified for this item; refer to CoA/Spec Sheet.
• Research use only: Not for human or veterinary use.

Structure & Identity

• Item identity specific to this catalog entry:
  • CAS: 134044-97-6
  • SKU: A1445246
  • Product name: Aciculatin
  • Category: Life Science research chemical (research use only)
• Item-specific identifiers not provided in Product Data:
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Structural description (literature/general):
  • Aciculatin is reported in the literature as a plant-derived polyphenolic flavonoid C‑glycoside (natural product) isolated from grasses (e.g., Chrysopogon/Desmostachya spp.).
  • Typical features of a flavone C‑glycoside include: a flavone (2-phenyl-4H‑1‑benzopyran‑4‑one) aglycone bearing phenolic –OH groups and a sugar moiety C‑linked to the A‑ring (commonly at C‑6 or C‑8) rather than O‑glycosidically.
  • 2D structure in words (literature): a fused benzopyranone (chromen‑4‑one) scaffold with a pendant phenyl ring at C‑2; multiple phenolic substituents on the rings; a hexose ring attached via a carbon–carbon bond to the flavone A‑ring. No stereocenters are typically present in the aglycone; the sugar confers multiple stereocenters.
• Stereochemistry (literature): sugar moiety possesses defined configurations at the hexose centers; the aglycone is planar/aromatic.

Synthetic Utility

Although not commonly used as a building block, aciculatin is valuable in synthetic chemistry as a benchmark target and as a reactivity probe.

• Benchmark target (literature/general):
  • The C‑glycosidic linkage and polyphenolic substitution pattern make it a representative challenge for total synthesis and for method development in regioselective C‑glycosylation of flavones.
  • Serves as a reference for studying late-stage diversification of flavonoids (e.g., selective O‑acylation/methylation) while preserving a C‑glycoside.
• Reactivity handles (general):
  • Phenolic –OH groups: amenable to protection (Me/Ac/Bz) and ether/ester formation; also enable metal-chelation experiments.
  • Conjugated carbonyl (chromen‑4‑one): participates in hydrogen bonding and can be selectively reduced or derivatized under mild conditions in model studies (ensure compatibility to avoid C‑glycoside cleavage).
• Analytical synthetic utility:
  • Used to validate synthetic C‑glycosylation methods by co-injection and MS/MS matching of natural and synthetic material.
  • Fragmentation pathways of C‑glycosides vs O‑glycosides furnish diagnostic ions; helpful for structure elucidation workflows.
• Limitations:
  • The complex, sensitive structure is not ideal for routine multistep transformations; most applications are comparative or method-development in nature rather than preparative synthesis.

Target Specificity

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