Isoagarotetrol - ≥98% , CAS No.104060-61-9

CAS: 104060-61-9 Cat. No.: I988625 Formula: C₁₇H₁₈O₆ Peso molecolare: 318.32 PubChem CID: 21636029

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

Sorrisi canonici

C1=CC=C(C=C1)CCC2=CC(=O)C3=C(O2)C(C(C(C3O)O)O)O

IUPAC Name

(5S,6R,7S,8R)-5,6,7,8-tetrahydroxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromen-4-one

InChIKey

CWMIROLCTHMEEO-XUWVNRHRSA-N

INCHI

1S/C17H18O6/c18-11-8-10(7-6-9-4-2-1-3-5-9)23-17-12(11)13(19)14(20)15(21)16(17)22/h1-5,8,13-16,19-22H,6-7H2/t13-,14+,15-,16+/m0/s1

Isomeri SMILES

C1=CC=C(C=C1)CCC2=CC(=O)C3=C(O2)[C@@H]([C@H]([C@@H]([C@H]3O)O)O)O

PubChem CID

21636029

Peso molecolare

318.32

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Pyrans
      • Subclass Pyranones and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Pyrans
• Subclass: Pyranones and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyranones and derivatives
• Alternative Parents: Benzene and substituted derivatives Heteroaromatic compounds Secondary alcohols 1,2-diols Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pyranone - Benzenoid - Monocyclic benzene moiety - Heteroaromatic compound - Secondary alcohol - 1,2-diol - Oxacycle - Polyol - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as pyranones and derivatives. These are compounds containing a pyran ring which bears a ketone.
• External Descriptors: Not available

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

Proprietà chimiche e fisiche

• Peso molecolare: 318.320 g/mol
• XLogP3: -0.800
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 318.11 Da
• Monoisotopic Mass: 318.11 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 531.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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 tested bioassay or immunoassay protocols are provided in the Product Data for this SKU. General handling guidance for analytical or screening workflows:

• Stock solution preparation (general): Dissolve in anhydrous DMSO (e.g., 10–50 mM). Vortex and, if needed, sonicate briefly. Filter (0.22 µm PTFE) for LC use.
• LC-MS calibration: Prepare serial dilutions in ACN/H2O (1:1, +0.1% formic acid or 5–10 mM ammonium acetate), bracketed by blanks. Store aliquots at −20 °C for long-term reference stability if required.
• GC-MS (after silylation): React with BSTFA/MSTFA, quench excess, and inject promptly to minimize back-hydrolysis.

These are general recommendations only. Validate conditions for your instrumentation and sensitivity requirements.

Biological Roles

No biological function is specified for this catalog item. The following is general literature context and not a medical/clinical claim.

• Natural occurrence: Isoagarotetrol is reported in the agarwood chemical space, which comprises sesquiterpenoids and highly oxygenated small molecules linked to resinous heartwood formation in Aquilaria/Gyrinops species.
• Biosynthetic context (literature): Such compounds derive from terpenoid pathways (farnesyl pyrophosphate precursors), followed by extensive oxidation/hydroxylation steps; isomerization yields families such as agarotetrol and isoagarotetrol.
• Ecological role (literature): Oxygenated sesquiterpenes are often associated with plant defense and resin formation; they can contribute to the characteristic aroma and resin quality markers of agarwood.
• Analytical relevance: Due to structural specificity, iso/agarotetrols serve as chemical markers for authentication and chemotaxonomic studies.

Research-only notice:

• This product is supplied strictly for research use only (as stated). It is not intended for human or veterinary use, diagnostics, foods, or cosmetics.

Buffer Applications

Isoagarotetrol is a neutral, non-ionic small molecule and is not typically used to formulate buffer systems or control pH.

• If preparing aqueous assay solutions, dissolve first in DMSO or MeOH, then dilute into the target buffer (e.g., phosphate, HEPES, ammonium acetate) while monitoring for precipitation.
• For LC-MS applications, volatile buffers (ammonium formate/acetate, 2–20 mM) are recommended to preserve ionization efficiency. This guidance is general and not specific to the item’s certified properties.

Green Alternatives

As a solid small molecule (not a process solvent), “greener alternatives” pertain mainly to the choice of handling solvents and derivatization reagents.

Greener solvent considerations (general):

• Prefer ethanol or methanol (renewable feedstocks available) over chlorinated solvents. For high solubility needs, consider propylene carbonate or ethylene carbonate blends as greener high-permittivity options when compatible with analytics.
• For LC work, water/ethanol or water/acetonitrile gradients minimize environmental impact versus DMF/DMSO-heavy systems; retain a small DMSO cosolvent only as needed.

Comparison (general guidance):

• DMSO vs Ethanol
  • Solubilizing power: DMSO > EtOH
  • Greenness/biodegradability: EtOH > DMSO
  • Viscosity and volatility: EtOH easier to remove; DMSO harder to dry

Reagent selection:

• For protection chemistry, replace benzylation (requires hydrogenolysis) with carbonate-based protecting groups (e.g., dimethyl/di-tert-butyl carbonates) that can be removed under milder, less wasteful conditions where applicable.
• Favor organocatalytic or enzymatic acylations (e.g., lipase-catalyzed) in green solvents to reduce metal waste and harsh reagents.

Waste minimization:

• Use micro-scale derivatizations for GC-MS method development.
• Employ solid-phase extraction (SPE) to reduce solvent volumes during sample cleanup.

Note: Verify analytical compatibility before substituting solvents/reagents, particularly for LC-MS.

Pharmaceutical Uses

No pharmacopoeial status or excipient role is provided in the Product Data.

• Typical research-only roles (general):
  • Reference standard for natural product profiling and authentication (e.g., agarwood constituents).
  • Impurity/marker analysis in herbal raw material QC.
• Formulation relevance: As a polyol without strong chromophores, isoagarotetrol is not commonly used as an excipient. If employed in discovery biology, it is handled as a stock solution in DMSO/MeOH and dispensed at low microliter volumes.

Regulatory note:

• Supplied for research use only; not for therapeutic, diagnostic, or clinical application. No claims of safety or efficacy are made or implied.

Physical Properties

Item-specific specifications are not provided in the Product Data and should be verified on the CoA/SDS for the supplied lot.

• Appearance (catalog): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable for a polyol (decomposes before distillation) — exact value not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general/literature): Polyols of this class are typically soluble in DMSO, methanol, ethanol, and aqueous-organic mixtures; sparingly soluble to insoluble in nonpolar solvents (hexane, cyclohexane). Water solubility can vary with hydroxyl pattern and stereochemistry.
• Partitioning (literature expectation): Low logP relative to hydrocarbon sesquiterpenes due to multiple –OH groups; however, still sufficiently hydrophobic to prefer organic media unless ionized/derivatized.
• Hygroscopicity (literature): Multi–OH natural products may exhibit mild hygroscopicity and strong hydrogen bonding; they often form amorphous solids or high-melting crystalline powders.

Practical notes (general):

• Dissolve initially in a small volume of anhydrous DMSO or MeOH, then dilute with compatible media if needed. Gentle warming (≤40 °C) and sonication can assist dissolution; avoid prolonged heating to prevent degradation.

Quality and Grades

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

Context and implications:

• For small-molecule reference standards such as isoagarotetrol, suppliers typically control identity by 1H/13C NMR, HRMS, and HPLC/UPLC purity. When grade is unspecified, verify the lot’s actual assay (%), chromatographic purity, and residual solvent limits on the CoA.
• If offered as a library/ screening compound (per Category: 小分子和化合物库), expect packaging in milligram quantities with documentation supporting structural identity and purity thresholds compatible with discovery workflows.
• UV transparency is often limited for polyols lacking strong chromophores; if you require HPLC quantitation by UV, confirm the wavelength response or consider derivatization for enhanced detection.
• Stabilizers: None indicated in the Product Data. If your application is trace analysis or quantitative reference use, verify absence of additives on the CoA.

Quality verification checklist (recommended):

• Confirm lot-specific purity (area% by HPLC) and identity (NMR/MS).
• Review water content (Karl Fischer) if moisture-sensitive procedures are planned; Not specified for this item—check CoA.
• Confirm any inorganic/metal impurities if relevant to your method; Not specified for this item—check CoA.

Always match your application (analytical reference, discovery screening, or synthetic precursor) to the documented grade.

Reaction and Applications

Manufacturer Applications: Not specified in the Product Data for this SKU. The following expands on common uses of isoagarotetrol-like standards in research settings (literature/general):

• Reference standard for agarwood chemistry: Used to support authentication and quality assessment of agarwood by LC/GC-MS profiling, where iso/agarotetrols and complementary sesquiterpenes serve as marker constituents.
• Analytical method development: Calibration of retention times and MS response in targeted analyses of polyhydroxylated sesquiterpenoids; matrix-spike recovery studies in plant extracts.
• Derivatization chemistry:
  • Selective acylation/silylation (e.g., TMS, MSTFA, acyl anhydrides) to improve GC volatility/detection.
  • Stepwise protection–deprotection strategies (e.g., TBDMS, TIPS, benzyl) to interrogate structure–activity or to prepare analogs.
• Synthesis/semisynthesis: Serves as a polyol scaffold enabling oxidation (TEMPO/Pinnick for primary OH to acids; Swern/DMP for secondary OH to ketones), etherification (Williamson), and carbonate/urethanes formation.

Practical tips (general):

• Many polyols are air-stable but can undergo slow oxidation; maintain neutral to slightly acidic conditions during storage.
• For GC-MS method development, consider silylation to enhance volatility; ensure complete derivatization to avoid peak splitting from partial products.
• In LC-MS, negative-mode ESI may show poor response; adduct formation in positive mode (NH4+, Na+) can be exploited for sensitivity.

Reaction Conditions

General conditions relevant to polyol derivatization and analytical preparation; adapt to your substrate and confirm with small-scale trials.

• Silylation for GC-MS: BSTFA or MSTFA (with 1% TMCS), 60–70 °C, 20–60 min; anhydrous acetonitrile or pyridine. Ensure glassware dryness; verify completion by disappearance of –OH in IR/NMR.
• Steglich esterification: Carboxylic acid (1.2–2.0 eq), DCC or EDCI, catalytic DMAP, dry DCM or ACN, 0 °C to rt, 2–18 h. Monitor for overacylation on multiple –OH sites.
• Carbonate formation: CDI (1.2–1.5 eq) in THF/ACN, rt, then nucleophile addition. Alternatively, triphosgene (carefully, in fume hood) with base at 0–25 °C.
• Selective oxidation (primary OH): TEMPO (5–10 mol%), NaOCl/KBr, pH ~9–10, 0–5 °C to rt; or TEMPO/BAIB in MeCN/H2O at rt. For secondary OH, DMP or Swern, −78 to 0 °C.
• Etherification: NaH or KH (1.1–1.5 eq) in THF/DMF at 0–25 °C, then alkyl halide; protect other OH groups to control selectivity.

Workup and purification tips:

• Polyols often streak on silica; use gradient polarity (hexane/EtOAc to EtOAc/MeOH), or ion-exchange resins if acidic/basic groups are introduced.
• For analytical standards, finish with vacuum drying (ambient–40 °C) to remove high-boiling solvents.

Expected yields: Highly substrate- and site-selectivity dependent; multi–OH substrates can give mixtures if not carefully protected. Optimize stoichiometry and order of protection.

Safety and Handling

Safety details specific to this catalog item are not provided in the Product Data. Always consult the SDS for authoritative guidance.

• GHS Classification / Pictograms / H-Statements: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• General hazard profile (literature/analogues): Neutral, polyhydroxylated natural products commonly present low acute toxicity by dermal or inhalation routes but may cause eye/skin irritation. Dusts can be nuisance particulates; avoid inhalation.
• PPE: Safety glasses, lab coat, and disposable nitrile gloves as a minimum. Use dust mask or local exhaust ventilation if handling fine powders.
• Handling: Avoid dust generation; handle in a clean, dry environment. Prevent cross-contamination—particularly if the compound will be used as an analytical reference standard.
• Incompatibilities (general): Strong oxidizers; moisture may affect weighing accuracy for hygroscopic polyols. Avoid strong acids/bases during storage.
• First aid (overview):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; seek medical attention if irritation continues.
  • Ingestion: Rinse mouth; seek medical advice.
• Spill response: Avoid dust; collect mechanically or with damp disposable towels. Dispose of in accordance with local regulations.

Note: The above are general lab safety practices. For this SKU, defer to the official SDS provided with the shipment.

Solvent Selection

Isoagarotetrol is a neutral, multi-hydroxyl natural product standard. Solvent choice primarily reflects the high hydrogen-bonding capacity and moderate polarity.

• Polarity class (general): Polar, protic functionality; behaves as a polyol. Prefers polar organic solvents.
• Recommended primary solvents (literature/practice):
  • DMSO: Excellent for preparing concentrated stock solutions for screening or analytics.
  • Methanol/Ethanol: Good solubility; compatible with LC-MS and many bioassay buffers after dilution.
  • Acetonitrile + small % water or MeOH: Useful for LC separations; solubility depends on composition.
• Limited solubility: Nonpolar hydrocarbons (hexane, heptane), weakly polar ethers (MTBE, diethyl ether) are typically poor.
• Aqueous handling: Direct water solubility may be limited and variable. For aqueous work, dissolve first in DMSO or MeOH, then dilute into buffer with vigorous mixing to avoid precipitation. Keep final DMSO ≤1–2% v/v when required by bioassays.

Comparison (general guidance):

• DMSO: maximum solubilization; hygroscopic, high boiling.
• MeOH/EtOH: greener profile than DMSO; lower solubilizing power than DMSO for hydrophobic polyols.
• ACN: strong eluent for LC; moderate solubility; low viscosity; often combined with water.

Tip: For recovery-critical workflows (qNMR, quantitative reference prep), precondition glassware and use anhydrous solvents to minimize variability from adventitious water.

Storage and Reconstitution

• Storage (catalog): Room temperature (per Product Data). Protect from moisture and direct light. For long-term archival of analytical standards, consider desiccated storage in the dark.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Form/Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution (general guidance):
  • Dissolve initially in anhydrous DMSO or methanol to prepare concentrated stocks.
  • For aqueous use, dilute the organic stock slowly into buffer with vigorous mixing to avoid precipitation; maintain final DMSO ≤1–2% v/v for typical bioassays.
  • If particulate persists, warm gently (≤40 °C) and/or sonicate; avoid prolonged heating.
• Aliquoting: To minimize freeze–thaw and moisture uptake, prepare single-use aliquots in amber vials or PCR tubes.
• Stability: Item-specific stability data are not provided; Not specified for this item—refer to CoA/Spec Sheet. As a general precaution for polyols, avoid strong acids/bases and oxidants during storage.
• Research Use Note: For research use only.

Always consult the accompanying CoA/SDS for lot-specific guidance on storage limits, shelf life, and solution stability.

Structure and Identity

Isoagarotetrol is a small-molecule natural product standard commonly associated with agarwood (Aquilaria/Gyrinops) chemistry. Item-specific identifiers below reflect the catalog entry.

• Catalog SKU: I988625
• Product Name: Isoagarotetrol
• CAS: 104060-61-9
• PubChem CID: 21636029 (literature identifier)
• InChIKey: 55533 (as provided; note: truncated/atypical format in Product Data)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• 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 (literature/general):

• The name “isoagarotetrol” denotes an isomer of “agarotetrol,” a known agarwood sesquiterpenoid/polyol. Literature reports iso/agarotetrols as highly oxygenated sesquiterpene frameworks bearing four hydroxyl groups (tetrol) and no ionic functionalities, consistent with a neutral, polyhydroxylated natural product standard.
• Expected 2D features (literature): compact carbocyclic sesquiterpene backbone with multiple secondary/tertiary alcohols; lacks halogens, nitro, or strong chromophores; stereochemistry is typically defined at several chiral centers (absolute configuration reported in natural product studies).

Notes:

• Exact stereochemical assignment, canonical SMILES, and definitive InChIKey should be confirmed from the Certificate of Analysis or authoritative databases for this specific lot. The above structural discussion is provided as general literature context for the compound name.

Synthetic Utility

Isoagarotetrol, by name and literature precedent, is a tetrol on a sesquiterpenoid skeleton, offering multiple functional handles for selective transformations and analog generation.

Functional group leverage (general):

• Alcohol chemistry:
  • Chemoselective protection (TBDMS/TIPS silyl ethers; benzyl/PMB ethers; cyclic acetals/ketals if carbonyls are introduced).
  • Esterification (Steglich; acid chloride/anhydride) for probe or prodrug-like derivatives in discovery research.
  • Oxidation of primary OH to aldehydes/acids (TEMPO/BAIB, DMP then Pinnick) and secondary OH to ketones (Swern/DMP), enabling skeletal diversification.
• C–O bond formation: Williamson ether synthesis on deprotonated alcohols; carbonate/urethane formation with phosgene equivalents (e.g., triphosgene) or green carbonates.
• Conjugation tags: NHS carbonates/carbamates or click handles (introduce azide/alkyne via carbonate/ester linkers) for analytical probes.

Strategic value:

• Dense functionality and stereochemistry make isoagarotetrol a testbed for selective protection/deprotection and site-selective acylation studies, and an entry point for SAR around agarwood sesquiterpenoids.

Analytical considerations:

• Derivatize (e.g., TMS ethers) to enhance GC volatility; for LC-MS, formation of formate/acetate adducts can improve detectability in ESI.

All transformations above are general/literature guidance for polyols and should be adapted once the exact stereochemical map for the supplied item is confirmed.

Target Specificity

Not applicable. Isoagarotetrol is a small organic molecule standard, not a biological macromolecule (e.g., antibody, enzyme, or ligand with defined biomolecular target in this catalog entry). No target/epitope, clone, isotype, or species-reactivity information applies.