This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
158.150 g/mol
XLogP3
0.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Exact Mass
158.058 Da
Monoisotopic Mass
158.058 Da
Topological Polar Surface Area
63.600 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
206.000
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
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Recensioni
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Application Protocols
No vendor-tested biological application protocols (e.g., WB, IHC, IF, FC) are provided for this small-molecule reagent. It is supplied for general research and synthesis.
General usage notes (informational):
Preparation of stock solutions: Dissolve in a suitable solvent (e.g., DMSO, methanol, or aqueous base) to a convenient concentration (e.g., 10–100 mM), filter (0.22 µm) if required for analytical work. Verify solubility first. (general)
Reference standard handling: For quantitative LC/GC, dry to constant weight if hygroscopicity is suspected; store aliquots to minimize repeated opening. (general)
Chiral analysis: If verifying enantiopurity, develop a chiral HPLC method or prepare a chiral derivative (e.g., Mosher ester/amidate) for NMR/LC analysis. (general)
For any application requiring validated conditions, consult peer-reviewed literature and perform internal qualification.
Biological Roles
Item-specific biological function data are not provided. The following are general considerations for small chiral carboxylic acids in biochemical and environmental research contexts:
Metabolic relevance: Simple carboxylic acids can participate in common metabolic pathways after activation to acyl‑CoA derivatives or through beta‑oxidation, depending on structure. However, terebic acid is not known as a primary human metabolite; treat as an exogenous research chemical unless your study demonstrates otherwise. (general)
Protein interactions: Carboxylates can chelate metal ions and engage in salt bridges with basic amino acid residues; such interactions are relevant in enzyme inhibition studies or binding assays when derivatized into ligands. (general)
Environmental chemistry: Certain small acids are investigated as components or markers of secondary organic aerosols in atmospheric chemistry; if using this compound as a standard, confirm identity and purity with the CoA and your analytical method. (general)
No medical or clinical properties are claimed or implied for this product. It is supplied strictly for research use only (Product Data).
Buffer Applications
This product is not a standard buffering reagent, and no buffer-use specifications are provided. For pH control in biochemical assays, established buffer systems (e.g., phosphate, acetate, Tris, HEPES, MOPS) are preferred.
If you wish to use this acid to adjust pH or as a component in a custom buffer, determine its pKa experimentally or from verified literature first, and evaluate ionic strength, compatibility, and biological effects in a pilot study. (general)
Note: Item-specific pKa and buffer capacity data are Not specified for this item; refer to CoA/Spec Sheet if available.
Green Alternatives
Greener practice considerations for using a small chiral carboxylic acid focus on solvent and reagent choices rather than on the acid itself.
Greener choices (general):
Solvents: Prefer ethanol, isopropanol, ethyl acetate, 2‑MeTHF, and water (when compatible) over chlorinated solvents or DMF/DMSO for workups and reactions. (general)
Coupling reagents: Consider T3P (in EtOAc), CDI, or DMTMM as alternatives to DCC/HOBt systems to reduce hazardous waste and mitigate explosive/acute toxicity risks. (general)
Energy: Many esterifications and amidations proceed efficiently at ambient temperature or with mild heating; employing microwave or flow can reduce reaction times and waste. (general)
Workup: Replace brine-heavy washes with minimal aqueous workups; use solid-supported scavengers where practical to cut solvent use. (general)
Illustrative comparison (general):
DMF/HATU vs. EtOAc/T3P
Hazard and waste: lower with T3P in EtOAc
Ease of removal: EtOAc is easily evaporated; DMF is persistent
Byproducts: T3P forms water-soluble, low-toxicity residues; HATU generates urea waste
Trade-offs:
Greener solvents may reduce solubility; process optimization (cosolvents, temperature, concentration) is often required.
Some alternative coupling reagents can be costlier; evaluate at scale with full EHS and cost-of-goods analyses.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or GMP manufacturing details are provided for this item. As listed, it is for research use only.
General considerations for small organic acids in formulation research (informational only):
May be explored as a counterion or co‑former in salt or cocrystal screening to modulate solubility and stability of APIs. Ensure toxicological acceptability before any preclinical use. (general)
Can serve as an intermediate for prodrug or ester formation studies aimed at modifying permeability or release; this remains strictly within laboratory research. (general)
Analytical reference: Potential use as a reference standard in method development (e.g., LC/UV, LC/MS) when studying related chemical spaces. (general)
No therapeutic claims are made or implied. This product is not intended for human or animal administration.
Physical Properties
Item-specific physical constants are not provided in the Product Data for this SKU. Where values are critical to your method, please consult the CoA/Spec Sheet for the supplied lot.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Do not substitute literature values without verification.)
Boiling point: Not applicable for most carboxylic acids that decompose or sublime before boiling at 1 atm; specific value Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable to solids; if an oil, Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general guidance):
Polar organics (e.g., methanol, ethanol, acetone) — typically moderate to high for small carboxylic acids (literature/general).
Water — variable; often improves with slight basification (formation of the carboxylate) (general).
Aprotic polar (DMSO, DMF) — typically high (general).
pKa: Not specified for this item; refer to CoA/Spec Sheet. Small aliphatic carboxylic acids typically have pKa ~4–5 (literature/general).
LogP: Not specified for this item; refer to CoA/Spec Sheet.
Notes for method development (general):
If using HPLC, acids are often retained on RP phases with modest aqueous content; ionization state (mobile phase pH) strongly affects retention.
For NMR, dissolve in DMSO‑d6, CD3OD, or D2O (with base) as appropriate; neutralization may sharpen signals by suppressing exchange.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret quality for this item (general guidance):
Enantiopure designation: The name “(R)-” denotes a defined absolute configuration. For chiral acids, manufacturers may report enantiomeric excess (ee) or enantiomeric ratio (er). Verify ee/er on the CoA if stereochemical purity is critical to your application.
Chemical purity vs. chiral purity: Both matter for stereosensitive syntheses, asymmetric catalysis benchmarks, or chiroptical studies. Ask for chromatograms (HPLC/GC) and chiral assay (chiral HPLC or GC) when needed. (general)
Residual solvents and water: For organic acids, loss-on-drying and KF water may be reported; confirm values on the CoA if your use is moisture-sensitive. (general)
UV impurities for analytical uses: If the material is to be used as a reference standard in LC/UV, request a low-UV cutoff grade or a spectrum to ensure minimal baseline interference. (general)
What is specific to this listing:
Storage at room temperature (Product Data). No other grade or purity attributes are provided here; rely on the lot-specific CoA/Spec Sheet for analytical details and acceptance criteria.
Reaction and Applications
This (R)-configured carboxylic acid can serve as a chiral building block, a reference standard, or a substrate in stereospecific transformations. While item-specific reaction data are not provided, the following uses are common for small chiral acids (general/literature guidance):
Amide bond formation: Coupling with amines via EDCI/HOBt, HATU, or T3P to generate amides while preserving stereochemistry at non-reacting stereocenters. Monitor for racemization if the stereocenter is alpha to the carbonyl. (general)
Esterification and transesterification: Fischer esterification in alcohols with acid catalysis; Steglich esterification in DCM/DMF with DCC/DMAP at ambient temperature. (general)
Activation/derivatization: Conversion to acid chlorides (SOCl2, oxalyl chloride + DMF) or anhydrides for further acylations; formation of NHS esters for bioconjugation. (general)
Chiral auxiliary/precursor: Depending on substitution, the (R)-acid may impart chirality to downstream products or serve in kinetic resolution studies. (general)
Analytical applications: Calibration standard for chiral HPLC/GC method development after derivatization (e.g., Mosher ester approach), or as a matrix component in studies of secondary organic aerosol markers if relevant to your research design. (general)
Practical tips:
Drying: If moisture-sensitive coupling is planned, azeotropically dry with toluene or co-evaporate with anhydrous solvents. (general)
Acid–base control: Use non-nucleophilic bases (DIPEA, NMM) to maintain solubility in aprotic media without forming salts that precipitate. (general)
Racemization vigilance: Keep temperatures moderate and avoid strong bases near stereocenters adjacent to carbonyls.
Reaction Conditions
No item-specific reaction condition data are provided. The following conditions are typical for small carboxylic acids and should be adapted based on the precise structure and sensitivity of this compound (general/literature guidance):
Amidation (EDC·HCl/HOBt or HATU):
Solvent: DMF, DCM, or MeCN
Base: DIPEA (2–3 equiv)
Temp: 0–25 °C
Time: 1–16 h
Notes: Minimize base and temperature if stereocenter is alpha to carbonyl to reduce racemization.
Steglich esterification (DCC/DMAP):
Solvent: DCM or DMF; 0–25 °C; 2–24 h
Notes: Filter off DCU; consider DIC to ease workup; catalytic DMAP accelerates reaction.
Acid chloride formation (SOCl2 or (COCl)2 + DMF cat.):
Solvent: neat or DCM; reflux (SOCl2) or ambient to reflux (oxalyl chloride)
Notes: Use anhydrous conditions; quench carefully; proceed directly to acylation when possible.
Borane reduction to alcohol:
Reagent: BH3·THF (1–2 equiv per CO2H)
Solvent: THF; 0–25 °C
Notes: Quench cautiously with MeOH/H2O; avoid over-reduction if other carbonyls present.
Decarboxylative coupling (if applicable):
Photoredox catalyst (Ir/Ru or organic), base (Cs2CO3), solvent (MeCN/DMA), blue LEDs, 20–40 °C, 4–24 h.
Always run small-scale trials and monitor by TLC/LC‑MS. Adjust equivalents and temperatures to the specific substitution pattern.
Safety and Handling
Authoritative safety classification (GHS, pictograms, hazard statements) is Not specified for this item; refer to the product SDS for definitive information. The following are general precautions for small organic carboxylic acids and enantiopure organic reagents used in research labs.
General hazards (informational):
May cause skin/eye irritation and respiratory tract irritation as dust or aerosol. Some acids can cause serious eye damage. (general)
Dust can be irritating; avoid inhalation and dust formation. (general)
PPE and engineering controls:
Wear lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood if dust, vapors, or aerosols may form. (general)
Handling advice:
Avoid contact with bases, strong oxidizers, and reactive acid chlorides/anhydrides unless intended. (general)
Hygroscopicity is possible for some acids; minimize exposure to ambient humidity until you verify the behavior of your lot. (general)
First aid (overview; defer to SDS):
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists. (general)
Ingestion/inhalation: Move to fresh air; rinse mouth; obtain medical advice. (general)
Spill and waste:
Small spills: Avoid dust; collect mechanically; neutralize residues with sodium bicarbonate; dispose per institutional and local regulations. (general)
Storage incompatibilities:
Separate from strong bases and strong oxidizers. Store tightly sealed to limit moisture ingress. (general)
Always consult the SDS for lot-specific, authoritative safety guidance.
Solvent Selection
Given the compound is a small chiral carboxylic acid, solvent behavior will be governed by acid–base equilibria and hydrogen bonding.
Polarity and miscibility (general guidance):
Polar protic solvents (methanol, ethanol, isopropanol): typically dissolve small acids well; facilitate esterifications under acidic conditions. (general)
Polar aprotic (DMSO, DMF, acetonitrile): good solvents for synthesis and analytics; useful for coupling reactions or derivatizations. (general)
Water: solubility varies; deprotonation (pH > pKa) greatly increases solubility as the carboxylate salt. (general)
Nonpolar (hexanes, toluene): limited solubility unless converted to less polar derivatives (esters, acid chlorides) or used as biphasic media. (general)
Selection by application (general):
NMR: DMSO‑d6 or CD3OD for neutral acid; D2O with a base (NaOD) if carboxylate form is acceptable. (general)
HPLC: reversed-phase aqueous-organic (water + 0.1% acid modifier)/acetonitrile or methanol; adjust pH to control ionization. (general)
Synthesis: For coupling to amines, use DMF, DCM, or MeCN with carbodiimide/uronium reagents and base; for esterification, use ROH with catalytic acid and molecular sieves. (general)
Comparison notes (general):
DMSO vs DMF: DMSO offers broader solubility but is harder to remove; DMF is easier to evaporate but more moisture sensitive in some couplings.
Methanol vs ethanol: MeOH typically increases solubility and reaction rates; EtOH offers greener profile and reduced toxicity.
Storage and Reconstitution
Storage conditions: Room temperature (Product Data). Protect from excessive humidity; store in the original, tightly closed container. If long-term storage is anticipated, consider desiccation as a precaution (general).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution: Not applicable to solids per se. For solution use, prepare fresh stocks in a compatible solvent (e.g., DMSO, methanol, or aqueous base), based on your application. Verify solubility experimentally. (general)
Stability in solution: Not specified for this item; refer to CoA/Spec Sheet. As general guidance, store solutions at 2–8 °C or −20 °C in amber vials, avoid repeated freeze–thaw, and use within days to weeks depending on solvent and concentration. (general)
Incompatibilities: Avoid strong bases or oxidizers during storage unless forming deliberate salts; prevent contact with acid chlorides/anhydrides that could react. (general)
Always refer to the product’s CoA/Spec Sheet and SDS for lot-specific handling and stability information.
Structure and Identity
Brief overview: This product is the (R)-enantiomer of terebic acid, a small chiral organic carboxylic acid. Item-specific identifiers provided below are limited.
SKU: T960376
Product name: Terebic acid, (R)-
CAS: 783349-41-7 (Product Data)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists a placeholder)
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 (general/literature notes, not item-specific):
Functional groups: contains at least one carboxylic acid group; carboxylates enable hydrogen bonding and metal coordination. (general)
Chirality: designated (R)-, indicating a defined absolute configuration at a stereogenic center. (general)
Polarity: polar, hydrogen-bond donating/accepting due to the acid group(s). (general)
2D description: a short aliphatic carbon chain bearing a carboxylic acid moiety and a stereocenter; additional unsaturation or oxygenation motifs are possible depending on exact substitution pattern. (general)
Identity and compliance:
Research use only; not for diagnostic or therapeutic use (Product Data).
For definitive identity attributes (InChI, SMILES, exact stereodescriptor), consult the CoA/Spec Sheet for the specific lot shipped.
Synthetic Utility
As a chiral carboxylic acid, the compound is a versatile handle for constructing amides, esters, and other carbonyl derivatives while transferring or preserving stereochemical information.
Key reactivity (general):
Nucleophilic acyl substitutions: Readily forms esters, thioesters, anhydrides, and amides under standard activation conditions (acid chloride, mixed anhydride, uronium/carbodiimide reagents). (general)
Reductions: Carboxylic acids can be reduced (e.g., via BH3·THF or mixed anhydride followed by NaBH4) to alcohols while maintaining configuration at remote stereocenters. (general)
Decarboxylative strategies: If suitably substituted, can participate in decarboxylative couplings under photoredox or transition-metal catalysis to forge C–C bonds from carboxylate precursors. Applicability depends on structure. (general)
Chiral derivatization: Formation of Mosher-type derivatives or chiral amides/esters to probe stereochemistry in NMR or to facilitate chiral separations. (general)
Retrosynthetic value (general):
The acid functional group enables late-stage diversification (amidation/esterification) without perturbing many protecting groups; useful in modular synthesis.
If the stereocenter is distant from the carboxyl, many manipulations proceed without racemization; if alpha to carbonyl, employ mild, non-basic conditions to preserve enantiopurity.
Analytical tips:
Confirm stereochemical integrity by chiral HPLC/GC or chiroptical methods (ORD/CD) after key steps.
Track residual coupling reagents and ureas by LC/MS to ensure clean downstream transformations.
Target Specificity
Not applicable. This product is a small organic molecule (a chiral carboxylic acid), not a biological targeting reagent (e.g., antibody, ligand with defined biomolecular target) provided with specificity data.
No antigen, epitope, species reactivity, clone, or isotype information applies.
For biochemical studies where this molecule is incorporated into ligands, any target specificity arises from the designed conjugate, not from the neat reagent itself.
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