Latifolin , CAS No.10154-42-4

CAS: 10154-42-4 Cat. No.: L996338 PubChem CID: 340211

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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.

Action Type

INHIBITOR

Names and Identifiers

Canonical Smiles

COC1=CC(=C(C=C1C(C=C)C2=CC=CC=C2O)O)OC

IUPAC Name

5-[(1R)-1-(2-hydroxyphenyl)prop-2-enyl]-2,4-dimethoxyphenol

InChIKey

OJVQOGDGFIJYPN-LLVKDONJSA-N

INCHI

1S/C17H18O4/c1-4-11(12-7-5-6-8-14(12)18)13-9-15(19)17(21-3)10-16(13)20-2/h4-11,18-19H,1H2,2-3H3/t11-/m1/s1

Isomeric SMILES

COC1=CC(=C(C=C1[C@H](C=C)C2=CC=CC=C2O)O)OC

PubChem CID

340211

NSC Number

370336

MeSH Entry Terms

latifolin

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Diphenylmethanes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Diphenylmethanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylmethanes
• Alternative Parents: Methoxyphenols Dimethoxybenzenes 4-alkoxyphenols Phenoxy compounds Anisoles Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Diphenylmethane - M-dimethoxybenzene - Dimethoxybenzene - Methoxyphenol - 4-alkoxyphenol - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Ether - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
• External Descriptors: Neoflavonoids

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

Chemical and Physical Properties

• Molecular Weight: 286.320 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 286.121 Da
• Monoisotopic Mass: 286.121 Da
• Topological Polar Surface Area: 58.900 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 333.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No item-specific tested application protocols are provided for this SKU.

General guidance (for small-molecule handling in research settings):

• Stock solution preparation: Dissolve compound in dry DMSO or methanol to prepare a 10–50 mM stock (as solubility allows). Vortex and, if needed, sonicate briefly. Filter through 0.22 µm PTFE before analytical use.
• Working solutions: Dilute stocks into assay buffer or mobile phase immediately before use. Keep final DMSO/MeOH content ≤0.5–1% v/v for most biochemical assays.
• HPLC/UPLC method development: Start with ACN/H2O or MeOH/H2O gradients (0.1% formic acid for UV/MS compatibility). Monitor at multiple wavelengths (e.g., 254, 280, 320 nm) to capture polyphenolic chromophores.
• Stability checks: Assess short-term stability at assay temperature and in light-exposed conditions; prepare fresh solutions daily if oxidative degradation is observed.

For any specialized application (e.g., derivatization, metal-complexation studies), consult primary literature pertaining to Latifolin and verify conditions with small-scale pilots.

Biological Roles

Scope: No medical/clinical claims are made. The following summarizes literature-based, general biochemical context for plant polyphenols akin to Latifolin.

• Natural origin (literature): Latifolin has been reported as a phenolic constituent of certain Dalbergia species and other hardwood taxa, where such compounds may function in plant defense and pigmentation.
• Chemical biology properties: Polyphenols commonly display redox activity and metal-chelating capacity due to phenolic OH groups and conjugation; these features can influence oxidative signaling and enzyme interactions in biochemical assays.
• Assay handling: For cell-free biochemical studies, compounds of this class are typically dosed from DMSO stock solutions with final organic content kept ≤0.5–1% v/v to control solvent effects (general practice).
• Metabolic considerations: Phenolic compounds are often subject to phase II conjugation (glucuronidation, sulfation) in mammalian systems and oxidative metabolism via peroxidases/monooxygenases in plants (literature, general), which is relevant when designing in vitro metabolic stability studies.
• Spectroscopic utility: Strong UV absorbance of the conjugated core enables straightforward tracking in protein-binding or partitioning studies using UV–Vis HPLC or spectrophotometric assays.

Item-specific biological role information is not provided; consult primary literature and the CoA for any characterization data associated with this SKU.

Buffer Applications

Not typically applicable. Latifolin is a small-molecule natural product and not used as a buffering agent. If incorporated into biological assays, it is usually delivered from an organic stock solution (e.g., DMSO or ethanol) into an existing buffer system (PBS, HEPES, Tris, etc.).

Practical notes (general):

• Keep final organic solvent ≤0.5–1% v/v to avoid perturbing buffer properties.
• Avoid high-pH buffers if phenolic stability is a concern, as deprotonation can accelerate oxidation.
• Filter-sterilize assay solutions when needed and prepare fresh working dilutions to minimize degradation.

Green Alternatives

Context: Latifolin is a solid analyte/standard rather than a process solvent; “green alternatives” primarily concern the choice of solvents and reagents used to dissolve, purify, or derivatize it.

Greener choices (general guidance):

• Dissolution: Prefer ethanol or methanol (renewable origin available) over DMF/DMSO where solubility permits. Consider water–ethanol mixtures with small DMSO cosolvent for assays.
• Chromatography: Favor EtOH/H2O or ACN/H2O (with minimal volatile buffers) over chlorinated eluents. Supercritical CO2 with polar modifiers is an option for preparative separations.
• Protection/activation reagents: For esterification, use enzymatic catalysis (lipases) in green solvents (2-MeTHF, CPME, EtOAc) when feasible instead of DCC; if carbodiimides are required, choose EDC·HCl in aqueous ethanol to reduce urea waste handling.

Comparison table (literature-based, not item-specific):

• DMSO vs EtOH: DMSO maximizes solubility but is harder to remove; EtOH is greener and volatile but may limit stock concentration.
• DMF/MeCN vs 2-MeTHF/EtOAc: Polar aprotics are effective for coupling; 2-MeTHF/EtOAc offer lower toxicity and better EHS profile, with potential trade-offs in solubility and reaction rates.

Operational tips:

• Minimize headspace oxygen and light exposure to reduce oxidative waste from degraded phenolics.
• Use microscale reactions and high-throughput screening to reduce solvent volumes in method development.

Pharmaceutical Uses

No item-specific pharmacopeial status or excipient role is provided for this product.

General context (non-clinical; for research and development use only):

• Polyphenolic natural products like Latifolin are occasionally used as analytical reference standards in pharmaceutical research to support botanical raw material identification, impurity profiling, or method validation.
• In pre-formulation research, such compounds may be explored for physicochemical characterization (solubility, pKa, lipophilicity) and compatibility with excipients; however, there is no indication this SKU is intended for formulation use beyond laboratory studies.
• If used in dosage-form research, dissolution typically relies on co-solvents (EtOH, PEG 400) or cyclodextrin inclusion complexes; these activities should be confined to non-clinical, exploratory settings.

For any regulated use, obtain full characterization (identity, purity, residual solvents, elemental impurities) and verify compliance with applicable guidelines. This product is designated: For research use only.

Physical Properties

Item-specific data from Product Data:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

Physical/chemical parameters (not specified for this item):

• Melting point, boiling point, density, refractive index, pKa, logP, UV–Vis maxima, water content/limits: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance (for context only; not item-specific specifications):

• Neoflavonoids and related polyphenols are typically crystalline solids with limited aqueous solubility and good solubility in polar aprotic/organic solvents (e.g., DMSO, DMF, MeOH, EtOH, acetone).
• Phenolic OH groups generally confer weak acidity (typical phenolic pKa ~8–10, literature) and enable hydrogen bonding; conjugation contributes to characteristic UV absorbance in the 250–380 nm range (literature), useful for HPLC/UPLC-UV detection.
• Thermal behavior often shows decomposition before boiling; careful control of drying temperature is recommended to avoid oxidative darkening of phenolics (literature).

Practical notes:

• For analytical preparation, dissolve small amounts in dry DMSO or MeOH to prepare primary stock solutions; dilute into assay media immediately before use to minimize oxidation (general best practice for polyphenols).
• If solid-state form (hydrate/solvate, polymorph) is relevant to your method, verify by XRPD/DSC/TGA as appropriate; consult the item-specific CoA.

Quality & Grades

Item-specific quality information:

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and guidance:

• When purity is not specified, assume research-grade material intended for laboratory research use only. For quantitative analytical workflows (e.g., as a reference standard), request a current CoA detailing assay purity (e.g., HPLC area %), water content (Karl Fischer), and residual solvents.
• For phenolic natural products, typical quality determinants include:
  • Identity: Confirmed by NMR (1H/13C), HRMS, and chromatographic purity (HPLC/UPLC with diode-array detection to check for coeluting congeners).
  • Purity profile: Reporting of related substances (isomeric/neoflavonoid impurities) is recommended for method validation.
  • Optical activity: If stereochemistry is relevant, a specific rotation or CD spectrum may be provided; otherwise, verify as racemic or achiral.
  • Residual solvents/metals/peroxides/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers: None indicated for this item. If oxidative sensitivity is a concern, consider aliquoting under inert atmosphere after receipt.

Documentation:

• Request batch-specific CoA and, if needed, a detailed specification sheet describing analytical methods, acceptance criteria, and storage/shipping conditions used for this SKU.

Reaction & Applications

Manufacturer Applications: Not specified for this item.

General research uses (literature/generic):

• Reference standard: Used as an analytical reference in phytochemical profiling and quality control of plant materials where Latifolin has been reported.
• SAR/assay studies: Polyphenolic scaffolds are commonly evaluated in biochemical assays; typical handling involves DMSO stocks and serial dilution (for research use only).

Chemical reactivity and derivatization (general):

• Phenolic OH transformations: Etherification (Williamson), esterification (Steglich/DCC–DMAP), carbonate/carbamate formation, and silylation (TBDMS/TMS) to modulate lipophilicity or protect groups for multistep synthesis.
• Electrophilic substitution: Activated aromatic rings may undergo halogenation, nitration (mild), or Friedel–Crafts-type acylation on less deactivated positions, subject to directing effects of phenols.
• Oxidation/reduction: Phenols can be oxidized to quinone-like species (e.g., with DDQ, Ag2O); carbonyl-containing cores (typical for neoflavonoids) allow reductions (NaBH4) or condensations (e.g., with hydrazines to hydrazones) for analytical tagging.
• Metal chelation: Ortho-dihydroxy motifs can chelate metals; useful for colorimetric complexation or as handles in affinity separations (literature).

Practical tips:

• Use anhydrous conditions for base-mediated O-alkylations; exclude air/light when prolonged heating is required to minimize oxidative degradation.
• For analytical derivatization (GC-MS), convert phenols to trimethylsilyl ethers (BSTFA + TMCS) to enhance volatility (if structure permits).

Reaction Conditions

No item-specific reaction condition data are provided for this SKU. The following are general literature-guided conditions relevant to phenolic polyphenols and neoflavonoid-like scaffolds (for research planning only):

• O-Alkylation (Williamson): Phenol (1.0 eq), NaH or K2CO3 (1.1–2.0 eq), alkyl halide (1.2–2.0 eq), dry DMF or acetone, 0–25 °C to reflux, 1–12 h. Protect from moisture and oxygen for sensitive substrates.
• Esterification (Steglich): Phenol (1.0 eq), carboxylic acid (1.2 eq), DCC (1.2 eq), DMAP (0.1 eq), CH2Cl2 or EtOAc, 0 °C to rt, 2–16 h. Filter dicyclohexylurea, purify by silica gel. Alternative: EDC·HCl/NHS in MeCN/EtOH–H2O.
• Silylation (TBDMS-Cl): Phenol, TBDMS-Cl (1.2–2.0 eq), imidazole (2.0 eq), DMF, rt, 2–6 h. Deprotect with TBAF in THF.
• Selective oxidation: Phenolic to quinone-like systems using DDQ (1.1–2.0 eq) in toluene/MeCN at 0–25 °C; monitor carefully to avoid over-oxidation (literature).
• Hydrogenation of aryl–alkenyl linkages: H2 (1–5 bar), Pd/C (5–10 wt%), EtOH/EtOAc, rt–50 °C, 1–6 h, if unsaturation is present and reduction is desired.

Yields are highly substrate-dependent; consult primary literature for Latifolin-specific transformations once exact substitution is confirmed. Always validate conditions on small scale and monitor by LC/MS or TLC with multiwavelength UV detection.

Safety & Handling

Item-specific hazard data (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 (not a substitute for SDS):

• PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid inhalation of dust/aerosols.
• Avoid: Contact with strong oxidizers and strong bases that can deprotonate phenolic OH groups aggressively; minimize exposure to air and light to reduce oxidative discoloration common to phenolics (general).
• First aid (overview): If inhaled, move to fresh air; if on skin/eyes, rinse with water for at least 15 minutes; if ingested, rinse mouth—seek medical attention in all cases. Follow institutional protocols.
• Spill response: Avoid dust generation. Collect mechanically or with HEPA-filtered vacuum. Dispose in accordance with local regulations.
• Fire safety: Many organic solids are combustible; use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and irritating fumes.
• Stability considerations: Polyphenols may undergo slow oxidation; store under recommended conditions, tightly closed, with desiccant/inert gas if long-term storage is planned.

Always consult the product-specific SDS for authoritative hazard classification, exposure limits, and emergency procedures.

Solvent Selection

Applicability: As a polyphenolic natural product, Latifolin is typically handled as a solid that requires organic solvents for dissolution.

General/literature-based solvent behavior (not item-specific specs):

• Polarity class: Moderate polarity solute due to phenolic OH groups and conjugation; favors polar protic and polar aprotic solvents.
• Good solvents: DMSO, DMF, methanol, ethanol, acetone, acetonitrile (literature). Solubility in nonpolar hydrocarbons (hexanes) is usually poor.
• Aqueous media: Limited intrinsic solubility at neutral pH; solubility increases with co-solvents (≤1–2% DMSO/EtOH) or at basic pH via phenolate formation (may affect stability/assays).

Selection guidance by application:

• Analytical stocks: Prepare concentrated stocks in dry DMSO or MeOH, then dilute into mobile phase or assay buffer immediately before use to limit oxidation.
• Preparative chromatography: Use MeOH/H2O or ACN/H2O with formic acid or ammonium formate if MS compatibility is desired; monitor at multiple UV wavelengths due to broad π→π* absorption.
• Derivatization reactions: Anhydrous polar aprotics (DMSO, DMF, MeCN) or alcohols under base/acid catalysis, depending on the transformation of phenolic OH.

Comparison (general):

• DMSO offers highest solvating power but can complicate lyophilization; MeOH/EtOH are greener but may provide lower maximum concentrations; ACN is volatile and MS-friendly but less green.

Storage & Reconstitution

Item-specific storage/shipping (from Product Data):

• Storage Conditions: Store at −20 °C.
• Shipped In: Ice chest + Ice pads.
• Research Use Note: For research use only.

General handling and reconstitution guidance (not item-specific specifications):

• Long-term storage: Keep tightly sealed in original container, protected from light and moisture. Consider storing under inert gas (argon/nitrogen) with desiccant for polyphenolic stability.
• Aliquoting: Upon first opening, promptly aliquot the solid or prepare concentrated stock solutions (e.g., in dry DMSO or MeOH), then store aliquots at −20 °C to minimize freeze–thaw and headspace oxygen exposure.
• Thawing: Allow vials to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation.
• Solution stability: Many phenolic compounds show limited stability in solution at ambient conditions; prepare fresh working solutions on the day of use. Avoid prolonged exposure to basic pH and light.
• Reconstitution tips: If dissolution is slow, gentle warming (≤40 °C) and brief sonication can help. Do not overheat; avoid aqueous-only media unless pH or co-solvent supports solubility.

For lot-specific stability/shelf-life and any recommended diluents, consult the product’s CoA/Spec Sheet and SDS.

Structure & Identity

Brief overview: Latifolin is a plant-derived polyphenolic natural product (literature) frequently classified among neoflavonoid/flavonoid-like constituents isolated from Dalbergia and related genera.

• Item-specific identifiers from Product Data:
  • CAS: 10154-42-4
  • CID: 340211
  • InChIKey: 259947 (as provided; note that this is not in standard 27-character InChIKey format)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Composition (item-specific):
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (general literature description, not item-specific):
  • Reported as an oxygenated aromatic polyphenol bearing multiple phenolic hydroxyl groups and a conjugated aryl–carbonyl framework typical of neoflavonoids.
  • Features likely include one or more benzene rings fused/connected to a heteroatom-containing ring or aryl carbonyl core; phenolic OH groups confer hydrogen-bond donor/acceptor capacity and metal-chelating propensity.
  • Expected to be largely planar across the conjugated core with rotatable aryl–aryl or aryl–alkenyl bonds depending on substitution (literature).
• 2D structure (descriptive, literature-based):
  • A substituted polyphenolic scaffold with an extended π-system; phenolic OH substituents ortho/para to each other on one or more rings; carbonyl functionality embedded in an aryl ketone or heterocyclic context typical of neoflavonoids.

Note: For definitive structural representation (SMILES, exact stereochemistry if any), consult the Certificate of Analysis/Spec Sheet for this specific lot.

Synthetic Utility

From a synthetic standpoint (general literature for phenolic neoflavonoids):

• Functional group handles: Multiple phenolic OH groups enable O-functionalization (alkylation, acylation, carbonate formation) and serve as protective group sites (e.g., TBDMS, benzyl, MOM). The conjugated aryl–carbonyl core allows further manipulation (reductions, condensations) for analog synthesis.
• Scaffold diversification: Late-stage diversification through selective O-alkylation/arylation (e.g., Ullmann–Goldberg, Buchwald–Hartwig for aryl ethers) or Mitsunobu inversion at secondary alcohol sites if present.
• Probes and tags: Installation of photoreactive (diazirine) or clickable (azide/alkyne) moieties via carbonate/carbamate linkers creates chemical biology probes while preserving the aromatic core.
• Analytical derivatization: Trimethylsilylation (BSTFA/TMCS) or acylation (acetic anhydride, TFAA) increases volatility/hydrophobicity for GC-MS or alters retention in LC for peak resolution.
• Retrosynthetic value: The scaffold exemplifies convergent assembly from substituted phenols and C3 units via Claisen–Schmidt-type condensations and cyclizations (common in flavonoid/neoflavonoid syntheses, literature), offering a platform to access analog libraries.

Note: The exact substitution pattern and stereochemistry for Latifolin determine reactivity/selectivity; consult structural data from the CoA or primary literature when planning site-selective transformations.

Target Specificity

Not applicable. This product is a small-molecule natural product, not a biological macromolecule or antibody. No antigen/epitope/clone/isotype or species reactivity data apply.