≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Store at 2-8°C,Protected from light,Desiccated Ships Wet ice Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Overview
Terminolic acid is a pentacyclic triterpenoid glucoside isolated from Combretum racemosum. Terminolic acid can inhibit the pro-inflammatory cytokines by binding to receptor active site of IL-1β and IL-6 , and enhance anti-inflammatory cytokines by binding to IL-4 receptor binding sites. Terminolic acid also exhibits moderate antibacterial activity.
Terminolic acid is a pentacyclic triterpenoid glucoside isolated from Combretum racemosum . Terminolic acid can inhibit the pro-inflammatory cytokines by binding to receptor active site of IL-1β and IL-6 , and enhance anti-inflammatory cytokines by bindin
Storage
Store at 2-8°C,Protected from light,Desiccated
Shipped In
Wet ice
This product requires cold chain shipping. Ground and other economy services are not available.
This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
External Descriptors
Not available
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.
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Application Protocols
Item-specific tested application protocols are not provided for this product. The following general practices apply to small-molecule triterpenoid standards in research settings.
Stock preparation (literature/general):
Dissolve in anhydrous DMSO to 10–50 mM. Sonication and gentle warming (≤40 °C) can aid dissolution. Filter (0.22 µm PTFE) if particulate remains.
For LC–MS reference solutions, prepare 0.1–1.0 mg/mL in MeOH or MeOH:water (80:20) with 0.1% formic acid as needed for peak shape.
Chromatographic analysis:
RP-HPLC: C18, 30–70% MeOH/H2O or ACN/H2O over 10–30 min, 1 mL/min, detect at 205–215 nm or use ELSD/CAD.
TLC: silica gel, hexanes:EtOAc 3:1 to 1:1; visualize with anisaldehyde–H2SO4 stain (triterpenoids give characteristic violet/blue spots after heating).
Biochemical assays:
Dilute DMSO stocks into buffer to final DMSO ≤1% v/v. Pre-mix with carrier protein (e.g., 0.1% BSA) or surfactant (0.01–0.05% Tween 20/80) to mitigate aggregation.
Always tailor protocols to your instrumentation and assay requirements; verify compatibility of vehicles and additives with your readout.
Biological Roles
This section summarizes general biochemical context for pentacyclic triterpenoids like terminolic acid; it is not specific to a therapeutic claim and is provided for research orientation only.
Origin and biosynthesis (literature/general):
Generated via the mevalonate pathway: squalene → 2,3-oxidosqualene → cyclization by oxidosqualene cyclases to ursane/oleanane scaffolds → oxidative tailoring (P450s) to introduce hydroxyls and carboxylation at C-28.
Common in Terminalia species and other angiosperms as part of cuticular waxes and defense-related metabolites.
Physicochemical biology:
Strongly hydrophobic backbone with a polar headgroup (carboxylate) promotes membrane association; forms micelles/aggregates above low µM in aqueous buffers without sufficient co-solvent or surfactant.
Research use implications:
Frequently examined as a chemotaxonomic marker and as a structural motif for SAR studies of triterpenoids in biochemical assays. Conjugation to fluorescent tags or biotin via the C-28 carboxyl enables affinity-based profiling of protein interactions in chemical biology workflows.
Metabolic handling (literature/general):
In biological systems, triterpenic acids can undergo glucuronidation/sulfation at hydroxyls or carboxylate and oxidation at allylic positions. Such transformations are relevant to in vitro metabolism studies.
All biological work should be framed as exploratory research; no clinical or diagnostic use is implied.
Buffer Applications
Terminolic acid is not a buffering agent and does not serve as a pH-controlling component in standard biochemical buffers.
Practical notes (literature/general):
When preparing assay buffers containing terminolic acid, use a co-solvent strategy (e.g., 0.1–1% DMSO or ethanol) and add compound as the final step with thorough mixing to avoid precipitation.
Inclusion of solubilizers (e.g., Tween 80, cyclodextrins, or BSA) can improve dispersion for biophysical assays; validate that additives do not interfere with the readout.
For pH control, use conventional buffers (HEPES, PBS, Tris, acetate) independently of the analyte.
Green Alternatives
While terminolic acid is a solid analyte rather than a bulk solvent/reagent, greener choices arise in its handling, purification, and formulation.
Solvent selection (literature/general):
Prefer ethyl acetate, 2-methyltetrahydrofuran (2-MeTHF), or isopropanol over chlorinated solvents when feasible for extraction and chromatography.
For stock solutions, aqueous co-solvent systems (e.g., 10–20% ethanol or propylene glycol) may replace DMF or chlorinated solvents for some analytical tasks.
Workup and purification:
Reversed-phase chromatography employing water/methanol or water/acetonitrile minimizes halogenated solvent use; consider supercritical CO2 for larger scale separations if available.
Energy and waste:
Exploit the high crystallinity of many triterpenoids to use recrystallization (EtOAc/hexanes, alcohol/water mixtures) instead of extended column chromatography, reducing silica and solvent waste.
Comparative snapshot (general):
DCM/CHCl3: excellent solubility, but high hazard and poor EHS profile.
EtOAc/2-MeTHF: greener, often adequate solubility; may require warming or co-solvents.
DMSO: useful for stocks; consider glycerol/PEG 400 blends where assay-compatible.
Adopt solvent substitution guided by the CHEM21 or ACS GCI solvent guides while maintaining analytical performance for your application.
Pharmaceutical Uses
This product is supplied strictly for research use. No medical or clinical claims are made.
Terminolic acid and related triterpenoids are commonly handled as analytical reference standards and for pre-formulation studies exploring solubilization of highly lipophilic acids.
Prototype formulation tactics include: lipid-based vehicles (oils, self-emulsifying systems), cyclodextrin inclusion complexes, and polymeric micelles; these are used in research to improve apparent solubility for in vitro testing.
Compendial status:
No pharmacopeial monograph is known for terminolic acid; treat as a non-compendial research chemical.
Manufacturing notes:
If used as a process intermediate or impurity standard in development settings, document handling conditions, stability indicating methods (RP-HPLC/UPLC, LC–MS), and reference standard qualification per internal SOPs.
Physical Properties
Item-specific specifications are not provided for this catalog entry. Do not treat the following as specifications; they are general/literature guidance for pentacyclic triterpenic acids like terminolic acid.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Melting point (literature/general): Many related triterpenic acids exhibit high melting points, often in the 250–300 °C range (decomp.). Exact value for terminolic acid should be verified from primary literature or CoA.
Boiling point: Not applicable (decomposes; macromolecular, nonvolatile). Literature typically reports no meaningful BP at ambient pressure.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (literature/general):
Water: negligibly soluble at neutral pH due to hydrophobic core and low acidity.
Organic: soluble in DMSO and DMF; sparingly to moderately soluble in hot ethanol, methanol, or acetone; soluble in chlorinated solvents (e.g., CH2Cl2, CHCl3) when neutral or esterified.
Aqueous basic media can increase apparent solubility via carboxylate formation (avoid prolonged exposure if structure-sensitive).
LogP (literature/general): High (typical of pentacyclic triterpenes; logP often >5), indicating strong hydrophobicity.
pKa (literature/general): Carboxylic acid typically pKa ~4.5–5.5; phenolic/basic functionalities are generally absent.
Refractive index: Not applicable for solids; not specified for this item.
Always consult the product’s CoA/SDS for exact physical data relevant to your lot.
Quality & Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Practical guidance on grading (general):
Research-grade triterpenoid standards are typically supplied with identity confirmation by NMR and/or HRMS, and purity by HPLC/UPLC or qNMR. UV cutoff, metal content, residual solvent levels, water content, and peroxides are generally not limiting for this class but may be reported on the CoA.
Where applicable, “HPLC grade” refers to low background in UV traces; for solid phytochemicals, look for “≥98% (HPLC)” or similar language on the CoA.
Stabilizers are generally unnecessary for terminolic acid; protection from light and moisture (desiccation) supports long-term stability.
What to check on receipt:
Verify lot-specific purity method (e.g., HPLC area %), identity (1H/13C NMR, MS), and water content if Karl Fischer is reported.
Confirm form supplied (free acid vs. salt/solvate) and any residual solvent declaration.
For exact acceptance criteria and analytical methods for SKU T646603, consult the Aladdin CoA/Specification Sheet for your lot.
Reaction & Applications
Manufacturer Applications: Not specified for this item; refer to catalog updates. The following outlines research uses typical for pentacyclic triterpenic acids like terminolic acid.
Reference standard and marker compound:
Utilized as a phytochemical reference for Terminalia and related genera in plant metabolomics, dereplication, and quality control (HPLC/LC–MS).
Derivatization chemistry (literature/general):
Carboxyl activation: Convert to acid chlorides (SOCl2, oxalyl chloride) or mixed anhydrides for amide/ester formation; peptide coupling (EDC/HOBt, DIC/DMAP) affords conjugates for probe development.
Hydroxyl protection: TBS/TBDPS or acetates facilitate selective oxidations or glycosylations; deprotection under standard conditions.
Oxidation/reduction: Secondary alcohols at C-2/C-3 can be oxidized (e.g., Dess–Martin) to ketones; hydrogenation of the 12-ene removes residual unsaturation.
Glycosylation: Formation of 3-O-glycosides (Koenigs–Knorr or modern donors) to modulate solubility and biointeractions.
Materials and conjugation:
Attachment to carriers (PEGs, dyes, lipids) via the C-28 carboxyl affords amphiphiles for nanoparticle or liposomal systems in research.
Analytical tips:
Poor UV chromophore; detection at 205–215 nm or evaporative light scattering/CAD is helpful. Derivatization (e.g., p-bromophenacyl esters) can enhance UV response.
All uses are for research and method development; no medical or clinical applications are claimed.
Reaction Conditions
General conditions below reflect literature practices for pentacyclic triterpenoid acids; optimize for your substrate and scale. They are not specifications for this item.
Esterification (Steglich):
Terminolic acid (1.0 eq), alcohol (2–5 eq), DCC or DIC (1.2 eq), catalytic DMAP (0.1 eq) in CH2Cl2 or DMF, 0 °C to rt, 4–24 h. Filter urea byproduct; purify by silica gel (EtOAc/hexanes).
Amide coupling:
EDC·HCl (1.2 eq), HOBt or HOAt (1.2 eq) or Oxyma, amine (1.2 eq), base (DIPEA, 2.0 eq) in DMF/CH2Cl2, 0 °C to rt, 6–18 h. Alternatively HATU/COMU for hindered partners.
Acid chloride formation:
SOCl2 (3–5 eq) with catalytic DMF, reflux 1–3 h; remove volatiles, use acyl chloride in situ with nucleophile at 0 °C to rt. Protect sensitive hydroxyls beforehand to avoid side reactions.
Alcohol protection:
TBSCl (1.5 eq), imidazole (3 eq) in DMF, rt to 50 °C, 2–12 h; or Ac2O/pyridine (rt) for acetate formation. Deprotect with TBAF (TBS) or mild base/acid (acetates).
Oxidation at C-3:
DMP (1.5 eq) in CH2Cl2, rt, 1–3 h; monitor by TLC/LC–MS. Avoid over-oxidation of allylic positions.
Hydrogenation of 12-ene:
H2 (1 atm), Pd/C (5–10 wt%), EtOAc or EtOH, rt, 2–6 h; watch for deprotection or over-reduction if other functionalities present.
Typical isolated yields in these transformations range from 60–90% depending on substitution and protection strategy (literature/general).
Safety & Handling
GHS/SDS information (item-specific):
Signal word: Not specified for this item; refer to SDS.
Hazard statements (H-codes): Not specified for this item; refer to SDS.
GHS classification and pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature/general):
Pentacyclic triterpenic acids are typically low volatility solids; primary risks are dust generation and solvent exposure during dissolution.
Avoid inhalation of dust and contact with skin/eyes. Use gloves (nitrile), lab coat, and safety glasses. Work in a chemical fume hood when weighing or preparing solutions (especially in DMSO/DMF/CH2Cl2).
Incompatibilities: Strong oxidizers; strong bases/acids may cause degradation (e.g., dehydration/ester hydrolysis). Avoid prolonged exposure to light/air at elevated temperature.
First aid (overview; defer to SDS):
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
Ingestion/inhalation: Move to fresh air; rinse mouth; obtain medical advice.
Special handling notes (item-specific storage):
Store at 2–8 °C, protected from light, desiccated (per Product Data). Shipments are on wet ice. Allow container to equilibrate to room temperature in a desiccator before opening to minimize moisture condensation.
Refer to the official SDS for authoritative hazard, toxicological, and regulatory information for this product.
Solvent Selection
Terminolic acid is a highly hydrophobic triterpenoid carboxylic acid; solvent choice strongly influences handling, weighing, and solution preparation.
Polarity and miscibility (literature/general):
Poorly soluble in water at neutral pH; solubility improves in basic aqueous media via carboxylate formation but may not be suitable for all assays.
Readily soluble in polar aprotic solvents (DMSO, DMF, NMP). Moderately soluble in ethanol/methanol when warmed; more soluble in dichloromethane, chloroform, or ethyl acetate than in acetonitrile.
Practical use cases:
Stock solutions for bioassays: DMSO at 10–50 mM is typical; dilute into assay buffer with final DMSO ≤0.5–1% v/v to minimize vehicle effects.
Purification: Normal-phase silica with CH2Cl2/MeOH or hexanes/EtOAc gradients; reversed-phase prep HPLC using MeOH/H2O or ACN/H2O with 0.1% acid for peak shape.
Comparison guidance (literature/general):
DMSO vs DMF: DMSO offers superior biocompatibility for stock solutions; DMF may extract plasticizers and is less favored in biological settings.
CH2Cl2/CHCl3 enable higher loadings but present greater health/environmental concerns; consider EtOAc or 2-MeTHF for greener workflows when possible.
Always confirm solubility empirically with your lot and application, and filter stocks (0.22 µm) where clarity is needed.
Storage & Reconstitution
Item-specific storage (from Product Data):
Store at 2–8 °C.
Protect from light.
Keep desiccated.
Shipped on wet ice.
Practical guidance (literature/general):
Allow vial to warm to room temperature in a desiccator before opening to prevent moisture condensation.
Reseal promptly after use; if available, backfill headspace with dry inert gas (N2/Ar). Store in an amber vial to limit photodegradation.
For long-term storage of solutions, prepare aliquots in anhydrous DMSO or MeOH, store at −20 °C to −80 °C, protected from light. Avoid repeated freeze–thaw cycles; use single-use aliquots.
Inspect periodically for signs of degradation (discoloration, precipitate, new HPLC peaks). Discard if quality no longer meets your acceptance criteria.
Reconstitution:
Select a solvent compatible with your application (DMSO recommended for concentrated stocks). Begin with a small volume and incrementally add solvent while vortexing/sonicating to full dissolution.
For any lot-specific stability or retest date, consult the Aladdin CoA/Spec Sheet. Research use only.
Structure & Identity
Terminolic acid is a pentacyclic triterpenoid carboxylic acid commonly encountered as a plant-derived secondary metabolite (research-grade standard).
Item-specific identifiers (from Product Data):
SKU: T646603
CAS: 564-13-6
PubChem CID: 12314613
InChIKey: 138232 (as provided 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):
Scaffold: pentacyclic triterpene (ursane/oleanane-type) with a carboxylic acid at C-28 and multiple secondary alcohols on the ring system.
Functional groups: one carboxylic acid (–CO2H), typically two to three secondary alcohols (–OH), multiple alkene-free saturated rings with a single internal olefin (–C=C–) around C-12 in many analogs.
Stereochemistry: richly stereodefined with ~6–8 stereocenters across the fused ring system; conventional absolute configuration follows the ursane/oleanane series.
2D description in words (literature/general):
A compact, highly hydrophobic, five-ring backbone (ABCD/E fused rings) bearing a terminal carboxyl at the C-17 side chain (28-position) and hydroxyl substituents on the A/B rings; one trisubstituted double bond on ring C (12-ene) is common among this class.
Note: Exact atom connectivity, stereochemistry, and alternative synonyms for terminolic acid should be confirmed against the supplied CoA/Spec Sheet for this catalog item.
Synthetic Utility
Terminolic acid offers a richly functionalized, stereodefined framework useful as a chiral pool starting material and for late-stage diversification in medicinal and chemical biology research.
Transformable handles (literature/general):
C-28 carboxylic acid: esterification (Fischer/Steglich), amidation (EDC·HCl/HOBt, HATU, COMU), acyl chloride formation (SOCl2) enabling further cross-couplings via acyl substitutions.
Secondary alcohols (e.g., 2α/3β): protection (TBS/TBDPS, acetyl), oxidation to ketones (DMP, PCC), or inversion via Mitsunobu to access epimeric derivatives.
12-ene alkene: epoxidation (m-CPBA), hydroboration–oxidation, or selective hydrogenation.
Conjugation chemistry:
Installation of linkers (PEG, azido/alkyne handles) at the carboxyl permits click-chemistry-enabled probes (CuAAC, SPAAC) for target engagement studies.
Retrosynthetic value:
Provides rapid access to a family of analogs (ester, amide, glycoside, carbonate, carbamate) while preserving the rigid pentacyclic core.
Analytical characterization:
1H/13C NMR exhibits characteristic upfield methyl singlets (angular methyls) and downfield signals for carboxyl carbon (~180 ppm); IR shows strong C=O stretch ~1690–1710 cm−1 and O–H bands.
These features make terminolic acid a versatile platform for structure–property and probe-development campaigns.
Target Specificity
Not applicable. Terminolic acid is a small-molecule triterpenoid and is not an antibody, enzyme, or targeted biologic. Any protein-binding studies would be exploratory and system-dependent; no target specificity data are provided for this item.
Frequently Asked Questions
What is the purity of this product?
This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at 2–8 °C, protected from light, desiccated. Keep the container tightly closed with desiccant — the material is moisture-sensitive.
How is this product shipped?
This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 564-13-6, the molecular formula is C30H48O6, and the molecular weight is 504.70 g/mol. InChIKey IDQVFXZQPGAVAM-GGVBUJAJSA-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.
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