This compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
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.
Soluble in water; Degree of Solubility in water: 1,250 g/l 25 °C
Punto di fusione (°C)
75 °C
Peso molecolare
168.100 g/mol
XLogP3
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
3
Exact Mass
168.027 Da
Monoisotopic Mass
168.027 Da
Topological Polar Surface Area
116.000 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
134.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
2
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
2
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Recensioni
Recensioni dei clienti
Application Protocols
No manufacturer-validated biological assay protocols are provided for this item.
General laboratory usage examples (literature-style, non-validated by manufacturer)
Preparation of 0.5 M tartrate buffer, pH 3.4: Dissolve mesotartaric acid in water to 0.5 mol/L (account for monohydrate formula weight), adjust pH with NaOH to 3.4, bring to volume, and filter (0.22 µm). Store at room temperature; check pH periodically.
Synthesis of diethyl mesotartrate: Suspend mesotartaric acid in absolute ethanol, add catalytic p-TsOH, reflux 12 h with a water trap (or slow ethanol removal/addition). Neutralize with Na2CO3, filter salts, concentrate, and recrystallize from ethanol/ether.
Formation of ammonium mesotartrate: Neutralize an aqueous solution with NH4OH to pH ~5, concentrate under reduced pressure at ≤40 °C, and crystallize by adding ethanol. Dry under vacuum.
Note: These are illustrative procedures for experienced chemists. Optimize conditions for your system and consult primary literature. For any application requiring validated conditions, develop and qualify an internal SOP.
Biological Roles
Applicability note: This section provides general biochemical context for tartaric acid systems; it is not a statement of biological activity for this specific catalog item.
Literature/General context
Occurrence: Tartaric acid occurs naturally in many plants, notably grapes and tamarinds. The meso isomer is less prevalent than the enantiopure L- or D- forms found in nature but can arise via epimerization and metabolic interconversion.
Biochemical behavior: As a small dicarboxylic acid with a vicinal diol, tartaric acid participates in acid–base equilibria and metal complexation; tartrate ligands are used in some enzymology protocols as stabilizers or inhibitors of metal-dependent processes (specifics depend on enzyme and metal ion).
Transport and metabolism: In microorganisms, tartrate can be metabolized via tartrate dehydratase and related pathways, generating oxaloacetate or other TCA intermediates, though isomer specificity varies by organism (literature).
Buffering: Within the pH 2–4.5 range, tartrate-containing buffers offer moderate capacity and can modulate metal ion availability through chelation.
Practical implications for lab work
Metal ion chelation by tartrates can alter catalytic activity or analytical outcomes; control for tartrate presence in assays involving transition metals.
Use of tartrate salts in crystallization can influence protein/peptide crystal packing through hydrogen bonding networks.
No medical/clinical claims
This product is for research use only. Any biological roles described are literature context and do not imply suitability for therapeutic or diagnostic use.
Buffer Applications
Applicability: Mesotartaric acid monohydrate can function as a diprotic acid component in low-pH buffer systems; however, tartrate buffers are less common than citrate/phosphate and are typically used when specific coordination properties are desired.
Relevant pKa values (tartaric systems): pKa1 ~2.9–3.0; pKa2 ~4.3–4.4. Effective buffering ranges are approximately pH 2.0–3.8 (acid form/first pKa) and pH 3.3–5.5 (second pKa).
Counterions: Sodium/potassium tartrate for near-neutral ionic strength; ammonium tartrate when volatility is desired in drying steps. Metal tartrates (e.g., Mg2+, Ca2+) will be influenced by chelation/complexation and possible precipitation.
Preparation example (literature-style): Dissolve mesotartaric acid in water to desired normality, adjust pH with NaOH to target (e.g., pH 3.4 or 4.2), and bring to volume. Filter (0.22 µm) for analytical applications. Monitor ionic strength and temperature as they slightly shift pKa.
Compatibility: Tartrate buffers can complex Fe3+, Cu2+, and other transition metals; this can be advantageous (masking) or detrimental (altered catalysis). Avoid in protocols sensitive to chelators.
Practical notes
Tartrate buffers exhibit modest UV absorbance above 200 nm, often acceptable for UV detection at λ ≥ 210–220 nm; verify baseline in your instrument.
For electrophoresis or cell culture: not commonly used; citrate, acetate, or MES-type buffers are usually preferred. Use tartrate buffers when specific literature precedent justifies them.
Green Alternatives
Context
Mesotartaric acid is part of the tartaric acid family, which can be sourced from renewable biomass (wine/grape industry). As such, it often aligns with green chemistry goals when used as an acidulant or building block.
Comparison to common mineral/organic acids (literature perspective)
Versus mineral acids (HCl, H2SO4): Tartrates are less corrosive/volatile, easier to handle, and derived from renewable resources. However, they generally provide weaker acidity and may introduce organic residues.
Versus petroleum-derived diacids (e.g., adipic, succinic from petro routes): Bio-based origin and biodegradability can be advantageous, though succinic acid is increasingly bio-produced as well.
Green processing tips
Use water or bio-derived alcohols (ethanol) as solvents where feasible; the high aqueous solubility of mesotartaric acid supports this.
For esterifications, adopt catalytic, solvent-minimized protocols (e.g., reactive distillation in ethanol) and avoid stoichiometric coupling reagents when not necessary.
Recovery/reuse: Unreacted acid can often be recovered by crystallization from aqueous ethanol. Salts can be regenerated to the free acid by ion exchange or acidification.
Snapshot tradeoffs
Renewable feedstock and low toxicity favor sustainability metrics.
Hygroscopicity and high polarity can complicate solvent-free processing and drying; dehydration can alter hydration state.
Scope note: No therapeutic claims are made. The following are formulation/manufacturing roles reported in the literature for tartaric acid derivatives; applicability to this specific item depends on grade and specifications, which are Not specified for this item; refer to CoA/Spec Sheet.
Literature/General formulation roles
Acidulant: Provides acidity in oral dosage forms, syrups, and effervescent tablets (often in combination with carbonates/bicarbonates). Mesotartaric acid, being achiral, lacks optical activity, but functional performance as an acidulant is comparable to other tartaric forms.
Co-crystal/salt former: Tartrate salts of APIs (especially amines) can enhance crystallinity, stability, and solubility. Selection between meso and enantiopure tartrate can affect crystal packing but not chirality transfer.
Taste modification: Contributes tartness similar to citric acid; used when tartrate salts are desired for compatibility.
Process aid: pH adjustment and chelation control in aqueous granulation; can influence metal-catalyzed degradation by binding trace metals.
Considerations
Grade compliance: Pharmaceutical use requires pharmacopeial or excipient-grade material with tight controls on impurities, water content, and microbial limits. For this SKU, such grade is Not specified for this item; refer to CoA/Spec Sheet.
Residual solvents and stereochemical purity (absence of L/D contamination) may be relevant in sensitive formulations.
Hygroscopicity/hydration: The monohydrate may exchange water depending on humidity; define LOD/KF limits for robust processing.
Documentation
For GMP or regulatory contexts, obtain full CoA, elemental impurity data (ICH Q3D), and residual solvent profile (ICH Q3C) for the specific lot.
Physical Properties
Item-specific (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.
Storage: Room temperature (as provided)
Literature/General properties (for context; not item specifications)
Solubility (qualitative, literature): very soluble in water; soluble in lower alcohols (e.g., methanol, ethanol); limited solubility in nonpolar solvents. Hygroscopicity is modest for the monohydrate compared with the anhydrous form due to lattice water.
Acid dissociation (literature): diprotic acid with pKa1 ~2.9–3.0 and pKa2 ~4.3–4.4 for tartaric acid systems; meso isomer is similar but may show minor differences depending on ionic strength/temperature.
Density/refractive index/UV cutoff: Not typically reported for this solid; consult primary literature if required for method development.
Thermal behavior (literature): melts/dehydrates with subsequent decarboxylation/anhydride formation upon strong heating; specific transition temperatures vary with hydration state and heating rate. Avoid prolonged heating above ~120–150 °C when integrity is critical.
Practical implications
Ready water solubility enables straightforward preparation of acidic aqueous stock solutions across pH ~1–4.
Strong hydrogen bonding favors crystalline salts and cocrystals; drying to constant weight may require gentle vacuum at ambient temperature to avoid dehydration.
For exact numeric specifications (mp, solubility values, water content, etc.) for this catalog item: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific (Product Data)
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on quality considerations for mesotartaric acid salts/acids
Typical quality attributes assessed: assay (acidimetric or by quantitative NMR), water content (especially relevant for hydrates), residual inorganic salts (sulfated ash), related stereoisomers (L-/D-tartaric acid), and organic impurities from synthesis (e.g., byproducts from epimerization or protection steps).
Hydration state: This listing is the monohydrate. Verify hydration by TGA/Karl Fischer or NMR integration if stoichiometry is critical. The monohydrate mass fraction of water is ~10.7% by theory (literature), but actual value for this lot is Not specified for this item; refer to CoA/Spec Sheet.
Optical properties: meso-tartaric acid is achiral (net [α]D ~ 0, literature). If optical neutrality is important (e.g., in chiral studies), confirm by polarimetry of an aqueous solution.
Trace metals/UV cutoff/peroxides: Not specified for this item; refer to CoA/Spec Sheet.
Choosing a grade
Analytical reagent (AR) or higher grades minimize nonvolatile residue and color, beneficial for analytical and materials workflows.
For synthetic applications (ester/amide formation), standard lab-grade material is typically adequate; however, chiral contamination (L/D isomers) can matter for stereospecific downstream steps—confirm enantiomeric content if relevant.
For chromatographic or spectroscopic applications, low-UV-absorbing/high-purity material reduces background; request HPLC/UV data if required.
Documentation
For this SKU, please consult the CoA/Spec Sheet for the definitive assay, stereochemical purity, water content, and impurity profile.
Reaction and Applications
General roles in synthesis (literature)
Polyfunctional building block: The 1,2-diol and α,α′-dicarboxylic acid groups enable orthogonal transformations—selective esterification, amidation, acetal/ketal formation, and oxidative cleavage.
Precursor to tartrate esters/amides: Formation of dimethyl/diethyl mesotartrate and diamides provides rigid, hydrophilic linkers in polymer and ligand design (note: meso diesters are achiral; contrast with D- or L-diethyl tartrate used as chiral auxiliaries).
Salt and cocrystal formation: Readily forms stable organic/inorganic tartrate salts. Although meso is achiral, tartrate salts can still modulate crystallization behavior and solubility of amines and metal ions.
Template/chelating behavior: Vicinal diol and diacid can chelate metals (e.g., Fe3+, Cu2+) under appropriate pH; useful in separations and materials synthesis.
Representative transformations (literature examples; conditions summarized in the Reaction Conditions tab)
Fischer–Speier esterification to mesotartrate diesters in lower alcohols with acid catalysis.
Carbodiimide-mediated coupling (EDC/DIC) to form diesters/diamides under mild, dehydrative conditions in aprotic media.
Protection chemistry: formation of isopropylidene ketals (acetonides) across the vicinal diol to direct selective acylations or to tune solubility.
Oxidative cleavage of vicinal diols (e.g., with NaIO4) to dicarbonyl fragments—useful analytically or to access short-chain dialdehydes (requires appropriate protection of carboxyls).
Thermal dehydration to tartaric anhydride (literature) as an intermediate for further acylation; handle with care due to potential decarboxylation.
Application spaces
Green chemistry feedstock: Tartrate derivatives originate from bio-based tartaric acid; meso form provides an achiral, symmetric scaffold for materials, ion-exchange ligands, and polymer crosslinkers.
Analytical chemistry: Standardizing acids, complexometric masking agents (at controlled pH), and matrix formers in some crystallization protocols.
Item-specific manufacturer applications: Not specified for this item in the catalog; see above for literature-based use cases.
Reaction Conditions
The following conditions are literature-style guidance for common transformations using mesotartaric acid; they are not specifications for this item.
Esterification (diesters/monoesters)
Fischer–Speier: Dissolve mesotartaric acid in dry ROH (MeOH or EtOH), add 0.5–1.0 equiv conc. H2SO4 or catalytic p-TsOH, reflux with a Dean–Stark (for higher alcohols) or remove water by azeotrope. Typical times: 4–24 h. Work up by neutralization and solvent removal; purify by recrystallization.
Carbodiimide-mediated: In CH2Cl2 or DMF, add alcohol (2–4 equiv), EDC or DIC (1.1–2.2 equiv per CO2H), and catalytic DMAP. 0–25 °C, 2–12 h. Minimize racemization concerns are irrelevant for meso but control O→N acyl transfer if amines are present.
Amide formation
Activate with EDC/HOBt (or Oxyma) in DMF, add amine (1.1–2.0 equiv per CO2H), 0–25 °C, 4–16 h. Alternatively, form acid chlorides (SOCl2, reflux, catalytic DMF) at low temperature, then couple with amines in base.
Protection of diol
Acetonide formation: Dissolve in acetone with catalytic acid (e.g., CSA or p-TsOH), 25–50 °C, 2–8 h; remove water by molecular sieves. Monitor by TLC/LC-MS.
Oxidative cleavage of diol (analytical)
NaIO4 (1.1–1.5 equiv per diol) in aqueous MeOH at 0–25 °C for 0.5–2 h. Control pH to avoid excessive decarboxylation; quench with ethylene glycol and remove salts.
Anhydride formation (dehydrative)
Heat under reduced pressure (≥120 °C) or treat with acylation reagents (e.g., Ac2O) cautiously; monitor to avoid decarboxylation. Use under inert atmosphere for reproducibility.
Solvents and atmosphere
Water and lower alcohols suffice for many steps; exclude water for coupling/esterification when high yields are desired. Inert atmosphere (N2) is recommended for moisture-sensitive couplings.
Typical yields
Diesters/diamides: 60–90% depending on conditions, purification, and steric factors (literature ranges).
Safety note
Exercise caution with strong acids, chlorinating agents, and carbodiimides; consult relevant SDS and reaction hazard assessments.
Safety and Handling
Item-specific (Product Data)
GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature.
Shipped in: Normal conditions.
Literature/General safety information (for context; defer to SDS for authoritative guidance)
Hazard profile: Organic dicarboxylic acids are typically classified as eye and skin irritants; dust may cause respiratory irritation. Not volatile; primary risk is via contact or ingestion.
Incompatibilities: Strong bases (rapid neutralization/heat evolution), reactive carbonyl compounds (possible esterification under dehydrating conditions), strong oxidizers (combustion enhancement). Avoid contact with reducing agents during high-temperature processing.
Peroxide formation: Not applicable (non-ether, non-autoxidizable solvent).
Thermal decomposition: Heating may lead to dehydration to tartaric anhydride and further decarboxylation, releasing CO/CO2 and acrid fumes.
Recommended PPE and engineering controls
Wear safety glasses with side shields, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Use a dust mask/respirator if handling large quantities of powder to minimize inhalation.
Handle powders in a fume hood or ventilated enclosure to control dust. Ground equipment when transferring bulk solids to minimize static.
First-aid overview (general)
Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing. Seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms develop.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product’s SDS for item-specific hazard statements, exposure limits, and emergency procedures.
Solvent Selection
Applicability note: This product is a solid reagent (diprotic acid), not a solvent. Solvent selection below refers to choosing media to dissolve or process mesotartaric acid monohydrate.
Water: highly soluble; forms clear solutions over a wide concentration range.
Alcohols (MeOH, EtOH): good solubility; solubility decreases with increasing hydrophobicity.
Polar aprotic solvents (DMSO, DMF): soluble; use for nonaqueous derivatizations (esterification, amidation) when water exclusion is necessary.
Nonpolar solvents (hexanes, toluene): essentially insoluble; use phase-transfer or convert to esters/salts for organic-phase processes.
Media selection by task
Acidic aqueous stock solutions (pH 1–4): water is preferred; ionic strength can be adjusted with inert salts if needed.
Esterifications/derivatizations: anhydrous alcohols (ROH) with catalytic acid or coupling reagents in aprotic solvents (e.g., CH2Cl2, DMF) depending on method.
Salt formation: neutralize with amines or metal bases in water or alcohols to obtain tartrate salts (useful for crystallization or materials applications).
Practical tips
To prepare concentrated aqueous stocks, warm gently (≤40 °C) and stir to accelerate dissolution; avoid high heat to prevent dehydration.
Filtering hot solutions can help remove particulates before crystallization of derivatives.
Comparison snapshot (literature)
Water vs ethanol: Water maximizes solubility and buffering capacity; ethanol enables water-sensitive coupling chemistry after azeotropic drying.
DMSO/DMF: Enable high concentrations and homogeneous activation with carbodiimides but require thorough workup to remove.
Storage and Reconstitution
Item-specific (Product Data)
Storage conditions: Room temperature.
Shipping: Normal.
General handling and storage guidance
Keep container tightly closed in a dry, well-ventilated place. Although a monohydrate is less prone to large mass changes than anhydrous forms, exposure to very dry or very humid air can shift the hydration state. Minimize headspace humidity swings by promptly recapping and, for analytical work, equilibrating samples to ambient conditions before weighing.
Avoid prolonged heating; store away from strong bases and oxidizers.
Reconstitution and solution preparation (literature guidance)
Aqueous solutions: Dissolve directly in DI water with stirring. For concentrated stocks, gentle warming (≤40 °C) can accelerate dissolution. Filter through 0.22 µm for analytical use. Label with concentration, pH, and preparation date.
pH adjustment: Use NaOH/KOH or volatile bases (NH4OH) depending on downstream needs. Tartrate buffers are effective around pH 2–5.
Organic solutions: For derivatization, dissolve in polar aprotic solvents (DMF, DMSO) or in alcohols under anhydrous conditions.
Stability notes
Solid-state: Stable at ambient temperature when dry and protected from incompatible reagents. Avoid light/heat during long-term storage to prevent slow dehydration or discoloration.
Solutions: Best used fresh; for short-term storage, keep at 2–8 °C. Extended storage may result in microbial growth in aqueous media—add appropriate biocide or sterile-filter and store cold if necessary.
For any item-specific limits (assay stability, water content range, shelf life): Not specified for this item; refer to CoA/Spec Sheet.
Backbone: HOOC–CH(OH)–CH(OH)–COOH, with the two hydroxyls on adjacent carbons; for the meso isomer, the substituents are oriented anti across the C2–C3 bond, giving an internal mirror plane.
Monohydrate: one equivalent of lattice water typically hydrogen-bonded to carboxylate/carboxylic acid and hydroxyl groups, contributing to a robust H-bond network in the crystal.
Notes
The literature identifiers/formula are provided for scientific context only and are not item-specific specifications. Always confirm exact structural identifiers for this lot in the CoA/Spec Sheet.
Synthetic Utility
Functional group leverage (literature)
Dicarboxylic acid: Enables diesterification, diamidation, and mixed-derivative synthesis to create linkers, crosslinkers, and pro-chelating ligands.
Vicinal diol: Allows acetonide/ketal formation, selective mono-acylations, and oxidative cleavage. The 1,2-diol also enhances metal-binding in assembled ligands or materials.
Meso symmetry: Provides an achiral, yet stereodefined scaffold—useful when a symmetric, rigid spacer is required without introducing optical activity.
Retrosynthetic value
Mesotartrate derivatives serve as precursors to symmetric C2-symmetric building blocks (e.g., meso diesters, diamides). They can be further elaborated via selective protection/deprotection to introduce asymmetry where needed.
Conversion to cyclic anhydride (under dehydrating conditions) offers a gateway to mixed anhydrides and further acyl transfer chemistry.
Integration into routes
Ligand/materials synthesis: Build polyhydroxylated, carboxylate-rich frameworks for metal–organic assemblies or ion-exchange materials.
Prodrug/linker design (non-clinical research): Provide hydrolyzable ester linkages with tunable hydrophilicity.
Analytical derivatization: Tartrate esters as polarity modifiers or chiral references (note: meso is achiral and serves as a non-rotatory comparator).
Practical considerations
Control hydration: Determine water content prior to stoichiometric reactions; pre-dry under vacuum at ambient temperature if needed to maintain monohydrate state or gently dehydrate as protocol demands.
Selective protection: Form acetonides before attempting stepwise esterification to avoid scrambling.
Avoid over-heating: Prevent decarboxylation during high-temperature steps; use mild coupling agents for amide/ester formation (EDC/DIC, HATU for amides with carboxyl activation).
Target Specificity
Not applicable to this product type.
This item is a small-molecule chemical reagent (mesotartaric acid monohydrate), not a biological affinity reagent or antibody. No antigen/epitope/clone/isotype information applies.
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K2127049