Dulcoside A - ≥98% , CAS No.64432-06-0

CAS: 64432-06-0 Cat. No.: D1049279 分子式: C₃₈H₆₀O₁₇ 分子量: 788.87 PubChem CID: 72941582

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

仕様と純度

≥98%

保管条件

Room temperature

純度

≥98%

名前と識別子

カノニカル・スマイル

CC1C(C(C(C(O1)OC2C(C(C(OC2OC34CCC5C6(CCCC(C6CCC5(C3)CC4=C)(C)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C)CO)O)O)O)O)O

IUPAC Name

[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

InChIKey

CANAPGLEBDTCAF-NTIPNFSCSA-N

INCHI

1S/C38H60O17/c1-16-12-37-10-6-20-35(3,8-5-9-36(20,4)34(49)54-32-29(48)26(45)23(42)18(13-39)51-32)21(37)7-11-38(16,15-37)55-33-30(27(46)24(43)19(14-40)52-33)53-31-28(47)25(44)22(41)17(2)50-31/h17-33,39-48H,1,5-15H2,2-4H3/t17-,18+,19+,20-,21-,22-,23+,24+,25+,26-,27-,28+,29+,30+,31-,32-,33-,35+,36+,37+,38-/m0/s1

異性体SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@@]34CC[C@H]5[C@@]6(CCC[C@@]([C@H]6CC[C@]5(C3)CC4=C)(C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)CO)O)O)O)O)O

PubChem CID

72941582

分子量

788.87

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • 分類 Prenol lipids
      • Subclass Terpene glycosides
        • Level5 Diterpene glycosides
          • Level6 Steviol glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• 分類: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Diterpene glycosides
• Direct Parent: Steviol glycosides
• Alternative Parents: Kaurane diterpenoids Fatty acyl glycosides of mono- and disaccharides O-glycosyl compounds Disaccharides Oxanes Secondary alcohols Carboxylic acid esters Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Acetals Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Steviol glycoside - Diterpenoid - Kaurane diterpenoid - Fatty acyl glycoside - Fatty acyl glycoside of mono- or disaccharide - Disaccharide - Glycosyl compound - O-glycosyl compound - Oxane - Fatty acyl - Secondary alcohol - Carboxylic acid ester - Organoheterocyclic compound - Polyol - Oxacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Acetal - Primary alcohol - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Alcohol - Carbonyl group - Organooxygen compound - Aliphatic heteropolycyclic compound
• 説明: This compound belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety.
• 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

化学的性質と物理的性質

• 分子量: 788.900 g/mol
• XLogP3: -0.700
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 9
• Exact Mass: 788.383 Da
• Monoisotopic Mass: 788.383 Da
• Topological Polar Surface Area: 275.000 Ų
• Heavy Atom Count: 55
• Formal Charge: 0
• Complexity: 1430.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 21
• 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 application protocols are provided in the Product Data for SKU D1049279. The following generic procedures are offered as non-binding guidance; adapt to your system and consult the CoA/SDS.

• Preparation of analytical standard (HPLC/LC–MS):

  1. Allow vial to equilibrate to room temperature (to avoid condensation).
  2. Accurately weigh an appropriate amount into a volumetric flask.
  3. Dissolve in methanol or water (or a 50:50 water–methanol mixture) to prepare a 1.0 mg/mL stock. Sonicate briefly if needed; avoid heating.
  4. Filter through 0.22 µm PTFE/NYLON filter into an HPLC vial. Store aliquots at 2–8 °C if analysis is not immediate.

• Enzymatic hydrolysis assay (example framework):

  1. Prepare 1–2 mM Dulcoside A in 50 mM citrate/phosphate buffer, pH 5.5.
  2. Add β-glucosidase or rhamnosidase (activity per supplier); incubate at 37 °C.
  3. Quench at timepoints with acetonitrile; analyze products by LC–MS.

These are general literature-style workflows and are not validated for this specific item. Always perform small-scale pilots to confirm solubility, stability, and analytical response.

Biological Roles

Literature-based overview (not item-specific):

• Origin: Dulcoside A is a steviol glycoside occurring in Stevia rebaudiana leaves as part of the plant’s secondary metabolite profile. These glycosides serve as storage/transport forms of the diterpenoid steviol.
• Structural biology/chemoreception: Steviol glycosides bind and activate the human sweet taste receptor (T1R2/T1R3) with varying potency depending on glycosylation pattern. Dulcoside A’s sugar composition modulates receptor interactions relative to stevioside and rebaudioside A.
• Metabolic fate (mammalian, in vitro/in vivo literature): Glycosidic bonds are hydrolyzed by gut microbiota or glycosidases to yield steviol, which is further conjugated (e.g., steviol glucuronide) and excreted. These pathways are well-documented for the class but are provided here solely for biochemical context.
• Enzymology: Subject to β-glucosidase and rhamnosidase activities; used as a substrate to profile glycosidase specificity and kinetics.
• Physicochemical-biological interplay: High polarity and multiple hydrogen-bonding sites underlie aqueous compatibility and receptor-binding characteristics, while limiting passive membrane permeability.

Note: The above describes general biological roles of the steviol glycoside class. This product is supplied strictly for research use; no nutritional, therapeutic, or clinical claims are made or implied.

Buffer Applications

Dulcoside A is not a buffering reagent and does not define a specific pH range. However, it is often handled in aqueous solutions for assays and analytics.

Practical guidance (general):

• Compatible media: Neutral phosphate-buffered saline (PBS), HEPES, or acetate buffers can be used to dissolve/dispense working solutions, provided pH is maintained near neutrality to limit hydrolysis.
• Concentration: Prepare fresh solutions at the lowest effective concentration for the assay. Gentle warming (≤40 °C) and brief sonication can assist dissolution.
• Filtration: Clarify with 0.22–0.45 µm membrane filters prior to HPLC/LC–MS to prevent particulates.
• Stability: Avoid strong acid/base; prolonged exposure below pH ~3 or above pH ~9 can promote glycosidic cleavage (general behavior for glycosides). Store aliquots to minimize freeze–thaw if refrigerated or frozen.

For applications that require tightly controlled ionic strength or metal chelation, select buffers that do not introduce nucleophiles or strong acids/bases. Always verify solution stability empirically for your specific conditions.

Green Alternatives

Dulcoside A is a target analyte/research substrate rather than a process solvent or commodity reagent; “green substitution” typically concerns the solvent system selected for its handling and analysis.

Greener choices for common operations (literature/guidance):

• Dissolution and sample prep:
  • Prefer water or aqueous ethanol over chlorinated solvents. These offer low toxicity and renewable content (ethanol).
• Chromatography:
  • Favor water–ethanol or water–acetone gradients where performance allows, instead of acetonitrile. Tradeoff: higher viscosity/backpressure and altered selectivity may require method re-optimization.
• Extraction from plant matrices (if applicable to your workflow):
  • Use hydroalcoholic systems (ethanol–water) under reflux or ultrasound rather than methanol-only; ethanol is bio-based and less toxic. Consider subcritical water extraction to reduce organic solvent use.

Comparison of eluents (general):

• Water–acetonitrile: High efficiency, low UV absorbance; higher environmental burden and supply volatility.
• Water–methanol: Broader availability; more toxic than ethanol, lower cost than ACN; higher backpressure.
• Water–ethanol: Greener profile; may reduce peak efficiency and alter selectivity; requires temperature control to manage viscosity.

Waste minimization:

• Implement micro-scale analytics (capillary/UPLC) to cut solvent volumes.
• Collect and segregate aqueous-organic waste for appropriate recycling or disposal per institutional guidelines.

Pharmaceutical Uses

No pharmacopeial or excipient grade is specified for this item; it is provided for research use only.

Literature and formulation-science context (non-clinical, not item-specific):

• Role as a taste-masking/sweetening agent in oral formulations has been explored for steviol glycosides. Dulcoside A, with distinct sweetness/bitterness notes versus stevioside/rebaudioside A, may be assessed in pre-formulation screening for palatability optimization.
• Compatibility: Typically compatible with many common excipients (cellulose derivatives, polyols); however, formulation pH and moisture content can affect stability via glycosidic hydrolysis.
• Analytical control: Reference standards of individual steviol glycosides assist in developing release tests (HPLC/UPLC with ELSD/UV/MS) to quantify glycoside composition in experimental dosage forms.
• Regulatory status: Not specified for this item; consult relevant regulatory frameworks if considering use beyond laboratory research. Steviol glycosides as a class have been evaluated in various jurisdictions for food applications, but this product is not supplied for food, cosmetic, or therapeutic use.

Conclusion: Treat Dulcoside A as a research chemical for formulation science studies and analytical method development. For any application beyond R&D, source appropriate grade and documentation.

Physical Properties

Item-specific specifications are not provided in the Product Data. Where helpful, general/literature characteristics for steviol glycosides are summarized; do not treat these as item specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Literature: off-white to white amorphous solid or crystalline powder for purified glycosides)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature range for steviol glycosides ~750–1000 g/mol)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Literature: many steviol glycosides decompose before clear melting)
• Solubility: Not specified for this item; refer to CoA/Spec Sheet. (Literature: sparingly to moderately soluble in water; soluble in polar protic solvents such as methanol and ethanol; low solubility in nonpolar solvents)
• Partitioning: Not specified for this item; refer to CoA/Spec Sheet. (Literature: strongly hydrophilic due to multiple hydroxyls; negative logD at neutral pH expected)
• pKa: Not specified for this item; refer to CoA/Spec Sheet. (Literature: carboxylic acid of steviol core typically pKa ~4–5; overall behavior dominated by neutral sugars)
• Optical rotation: Not specified for this item; refer to CoA/Spec Sheet. (Literature: steviol glycosides are optically active)
• Hygroscopicity: Not specified for this item; refer to CoA/Spec Sheet. (General: multi-hydroxylated glycosides can be mildly hygroscopic)

Always consult the CoA for lot-specific values and the SDS for additional physicochemical safety-related information.

Quality and Grades

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

Interpretation and implications (general guidance for steviol glycosides and natural product reference materials):

• Research-grade natural product standards are typically purified by multi-step chromatography (e.g., RP-HPLC) and may be characterized by NMR and HRMS. For applications such as method development, metabolite profiling, or taste-receptor studies, higher purity (≥95% by HPLC) is commonly desired. Exact purity for this SKU is not provided here; consult the CoA.
• Residual solvents, moisture content, and counterions: Not specified for this item; refer to CoA/Spec Sheet. Such attributes can affect solubility and analytical response.
• Stabilizers/additives: None stated. Not specified for this item; refer to CoA/Spec Sheet.
• Trace inorganic content/metals/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Best practices:

• Record lot number and retain CoA for data traceability in regulated labs.
• For quantitative analysis (e.g., external standard calibration by HPLC), confirm purity on receipt or apply purity correction using the CoA assay value.
• If using in biological assays, consider endotoxin/bioburden only if specified; otherwise treat as non-sterile research chemical.

Reaction and Applications

Manufacturer application details are not provided for this item. The following are general, literature-based research uses of Dulcoside A and related steviol glycosides; do not treat as product specifications.

• Natural product standard:
  • Use as an analytical reference for QC of Stevia extracts (HPLC/UPLC with UV/ELSD/MS detection).
  • Supports method validation (linearity, accuracy, precision) in food chemistry and natural products research.
• Taste receptor research (in vitro):
  • Probe interactions with human sweet taste receptor T1R2/T1R3 in cell-based assays; compare potency and efficacy across steviol glycosides. No clinical or nutritional claims are implied.
• Biotransformation and stability studies:
  • Assess enzymatic or microbial hydrolysis to steviol and intermediate glycosides; study glycosidase selectivity.
• Synthetic/semisynthetic derivatization (specialized):
  • Selective acylation/silylation of sugar hydroxyls to generate pro-analogs for structure–activity studies.
  • Controlled hydrolysis (acidic/enzymatic) to map glycosidic linkages.
• Chromatographic method development:
  • RP-HPLC with water–acetonitrile or water–methanol gradients; volatile acid modifiers (e.g., formic acid) for MS compatibility.

Practical considerations:

• Use neutral to mildly acidic mobile phases to balance stability and chromatographic performance.
• Avoid strong acids/bases during handling unless intentionally performing hydrolysis kinetics.

Reaction Conditions

General, literature-derived guidance for transformations relevant to Dulcoside A; these are not product specifications.

• Acidic hydrolysis of glycosides:
  • Solvent: Aqueous methanol or water.
  • Catalyst: Mineral acids (e.g., HCl, H2SO4) at millimolar to modest molar concentrations.
  • Temperature: 40–80 °C (monitor to avoid over-decomposition).
  • Outcome: Stepwise cleavage to mono-/diglycosides and steviol; track by HPLC/LC–MS.
• Enzymatic hydrolysis:
  • Enzymes: β-Glucosidase, rhamnosidase (source-dependent specificity).
  • Conditions: pH 5–6 citrate/phosphate buffer, 25–40 °C, hours to days.
  • Advantage: Selectivity and milder conditions; useful for linkage assignment.
• Ester derivatization at C-19 carboxyl:
  • Activation: Carbodiimide (EDC/NHS) in aqueous-organic systems or DCC/DMAP in anhydrous MeOH/DMF.
  • Temperature: 0–25 °C.
  • Note: Protect sensitive sugar hydroxyls if chemoselectivity is required.
• O-Acylation of sugar hydroxyls:
  • Reagents: Ac2O/pyridine or acyl chlorides with base (e.g., DMAP, pyridine).
  • Solvent: Anhydrous pyridine/DMF/DCM (as solubility permits).
  • Temperature: 0–25 °C; monitor closely to prevent overacylation.

Analytical conditions (method development tips):

• RP-HPLC: C18, water–acetonitrile or water–methanol gradient with 0.05–0.1% formic acid; ELSD or MS detection for non-UV chromophores.
• Stability: Avoid strong alkaline conditions and prolonged heating; prepare fresh standards to ensure quantitative accuracy.

Safety and Handling

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.

General handling guidance (for carbohydrate-rich natural products; literature-based, not product-specific):

• Low volatility solid; avoid generating dust. Use local exhaust ventilation when weighing or transferring. Prevent inhalation of particulates.
• Personal protective equipment: lab coat, safety glasses, and appropriate disposable gloves (e.g., nitrile). Change gloves regularly when handling powders and solutions.
• Incompatibilities: Strong oxidizers and strong acids/bases may degrade glycosidic linkages and the diterpene core. Avoid prolonged exposure to elevated temperature and UV light to limit hydrolysis/oxidation.
• First aid (general): If inhaled, move to fresh air; if on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes; if ingested, rinse mouth. Seek medical attention if symptoms persist. Follow institutional SDS-driven procedures.
• Fire safety: Organic solid; may burn if involved in a fire. Use water spray, CO2, dry chemical, or foam as appropriate for surrounding materials. Combustion may produce CO/CO2.
• Spill/cleanup: Avoid dust; sweep up gently or use HEPA-filtered vacuum. Dispose in accordance with local regulations.

Always defer to the product SDS for authoritative hazard classification, exposure controls, and disposal guidance.

Solvent Selection

Dulcoside A is a multi-hydroxylated glycoside; solubility favors polar protic media.

• Polarity class (qualitative, literature): Highly polar, hydrogen-bond donor/acceptor rich.
• Recommended solvents for stock solutions (general guidance):
  • Water or aqueous buffers: Often suitable at mg/mL levels; gentle warming and sonication can aid dissolution.
  • Methanol or ethanol: Good solubility; commonly used for analytical standards and extraction workflows.
  • DMSO: Effective co-solvent for preparing concentrated stocks for bioassays; dilute into aqueous media to final working concentrations to avoid precipitation.
• Poor solvents: Nonpolar hydrocarbons (hexanes, toluene) and weakly polar ethers typically provide negligible solubility.
• pH effects: Acidic or strongly basic conditions can promote hydrolysis of glycosidic bonds; prefer neutral pH for solution preparation unless hydrolysis is intended.

Comparison (general):

• Versus stevioside/rebaudioside A: Similar solubility profiles; subtle differences arise from sugar composition/branching. Method conditions validated for one often translate with minor adjustments (e.g., elution strength in RP-HPLC).
• Versus aglycone (steviol): Dulcoside A is substantially more water/MeOH soluble due to its sugar residues; aglycone prefers more organic content.

Practical tips:

• Filter solutions (0.22–0.45 µm) before HPLC/LC–MS.
• Avoid prolonged heating; prepare fresh solutions when possible to minimize degradation.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Practical guidance:

• Keep container tightly closed in a dry place, protected from light. If long-term storage is anticipated, many users store steviol glycosides at 2–8 °C in desiccated conditions to minimize hydrolysis—verify compatibility with this item and packaging.
• Moisture control: Multi-hydroxylated glycosides can absorb moisture; include desiccant in secondary containment when feasible.
• Reconstitution: For stock solutions, use water, methanol, ethanol, or DMSO depending on the intended application. Gentle swirling/sonication aids dissolution. Avoid strong acids/bases unless hydrolysis is intended.
• Solution stability: Prepare fresh solutions when possible. For short-term storage, aliquot and refrigerate (2–8 °C). For longer storage, frozen aliquots (−20 °C) may be used; minimize freeze–thaw cycles by dispensing single-use portions.
• Research use note: For research use only.

Always consult the product CoA and SDS for any lot-specific handling instructions, stability data, and packaging details.

Structure and Identity

Dulcoside A is a steviol glycoside (diterpenoid glycoside) isolated from Stevia species; it comprises the ent-kaurane steviol aglycone esterified with sugar residues.

• SKU: D1049279
• Product name: Dulcoside A
• CAS: 64432-06-0
• CID: 72941582 (reference identifier)
• InChIKey (from Product Data): 39068 (note: this is not a standard 27-character InChIKey; consult CoA/SDS for the definitive identifier)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature: steviol glycosides are C38–C44, highly oxygenated)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature: steviol glycosides typically ~750–1000 g/mol depending on sugar composition)

Structural features (general, literature):

• Core: ent-kaurane (tetracyclic) diterpene framework (steviol) with a carboxylate at C-19 and a secondary alcohol at C-13.
• Glycosidic substitution: O-glycosylation at the C-13 hydroxyl and ester glycosylation at the C-19 carboxyl; Dulcoside A commonly features glucose and rhamnose units in defined linkages.
• Stereochemistry: multiple defined stereocenters on the kaurane backbone and at glycosidic anomeric centers (predominantly β-D-glucose; rhamnose typically α-L).
• 2D description: fused trans-decalin bicyclic core extended to a tetracycle, bearing an exocyclic carboxylate side chain and a glycosidic chain; sugars linked via 1→2/1→3/1→6 O-glycosidic bonds depending on residue.

Note: For exact atom connectivity, anomeric configurations, and definitive identifiers of this specific lot, please refer to the Certificate of Analysis (CoA).

Synthetic Utility

While Dulcoside A is a complex natural product rather than a routine building block, it can serve as a useful substrate or reference in synthesis and methodology studies (literature-based guidance):

• Protecting-group chemistry: Multiple secondary hydroxyls enable selective protection (e.g., TBDMS, Ac, Bz) to probe site-selective transformations on carbohydrate moieties.
• Hydrolysis mapping: Controlled acid-catalyzed or enzymatic cleavage of glycosidic linkages provides access to partially deglycosylated analogs and the aglycone steviol, informing structure–activity relationships.
• Derivatization of the carboxylate: Activation (e.g., as mixed anhydride) followed by esterification/amidation can generate analog libraries; care must be taken to avoid transglycosylation or sugar degradation.
• Chemoenzymatic modification: Glycosyltransferases and glycosidases can remodel the glycan pattern to generate non-natural glycosides with altered physicochemical properties.
• Analytical synthesis utility: As a reference compound, Dulcoside A aids in calibrating retention and fragmentation behavior (LC–MS/MS), underpinning dereplication of steviol glycoside mixtures.

Caveats:

• The densely functionalized scaffold is sensitive to strong acids/bases and elevated temperatures; use mild conditions and orthogonal protections.
• Purification is typically by RP-HPLC or preparative chromatography due to polarity and structural similarity to congeners.

Target Specificity

This product is a small-molecule natural product, not a biological targeting reagent (e.g., antibody, inhibitor with defined protein selectivity panel). No target specificity data are provided in the Product Data.

General (literature) note: Steviol glycosides interact with the human sweet taste receptor (T1R2/T1R3) in chemosensory assays, but quantitative binding/activation constants for Dulcoside A vary by system and are not specified for this item. For receptor pharmacology, consult primary literature and validate under your assay conditions.

よくある質問

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 64432-06-0, the molecular formula is C38H60O17, and the molecular weight is 788.87 g/mol. InChIKey CANAPGLEBDTCAF-NTIPNFSCSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.