Glycerate (383-86-8) Physical and Chemical Properties
Glycerate
Glycerate is the conjugate base of glyceric acid — a small, highly polar hydroxy monocarboxylate anion used as a biochemical intermediate and versatile reagent in synthesis and analytical workflows.
| CAS Number | 383-86-8 |
| Family | Glycerates / hydroxy carboxylate anions |
| Typical Form | Powder or crystalline salt (solid) |
| Common Grades | EP |
Glycerate is the singly deprotonated anion of glyceric acid and belongs to the structural class of hydroxy monocarboxylate anions (2,3-dihydroxypropanoate derivatives). Structurally it is a three-carbon backbone bearing two vicinal hydroxyl groups and a terminal carboxylate function; the combination of a carboxylate and vicinal diol creates a high-polarity, hydrogen-bonding–rich surface and an anionic charge distribution localized on the carboxylate moiety with significant solvation by water. Electronically, the carboxylate group confers a negative formal charge while the vicinal hydroxyls provide strong hydrogen-bond donor capability and localized dipoles that alter solvation, conformer preferences and intramolecular hydrogen-bonding patterns.
These structural features lead to class-typical behaviour: pronounced aqueous solubility and low lipophilicity, strong propensity for hydrogen-bonding interactions, and readiness to form salts and esters. As a carboxylate/alpha-hydroxy system, glycerate participates in acid–base equilibria (as the conjugate base of glyceric acid), is readily phosphorylated or esterified in biochemical contexts, and is resistant to simple hydrolysis under neutral conditions but can undergo oxidative or dehydrative transformations under strong reagents. Biologically, glycerate is an endogenous metabolite and intermediate in glycerol and carbohydrate catabolism; pathological accumulation (e.g., due to glycerate kinase deficiency) is associated with metabolic disease and toxicity.
Common commercial grades reported for this substance include: EP.
Molecular Parameters
Molecular Weight and Formula
- Molecular weight: 105.07
- Molecular formula: \(\mathrm{C_3H_5O_4^-}\)
- Exact mass / Monoisotopic mass: 105.01878364
The formula corresponds to a three-carbon backbone with four oxygen atoms and a net single negative charge. The monoisotopic mass is useful for high-resolution mass spectrometry and isotope-resolved measurements.
Charge State and Ion Type
- Formal charge: \(-1\)
Glycerate is a carboxylate anion (monovalent), the conjugate base of glyceric acid. In solution it exists as an anionic species and commonly forms salts with counterions (e.g., sodium, potassium) or as part of ionic complexes. The anionic character dominates solvation and transport properties in aqueous systems.
LogP and Polarity
- XLogP (XLogP3-AA): -0.9
- Topological polar surface area (TPSA): 80.6
- Hydrogen-bond donors: 2
- Hydrogen-bond acceptors: 4
The negative XLogP and substantial TPSA indicate low lipophilicity and high aqueous polarity; the molecule is expected to be highly water-soluble and to partition poorly into nonpolar organic phases. Two hydroxyl donors combined with four acceptor sites produce strong intermolecular and intramolecular hydrogen-bonding capacity, which governs solvation, crystal packing of salts, and enzyme recognition in biochemical pathways.
Structural Identifiers (SMILES, InChI)
- SMILES: C(C(C(=O)[O-])O)O
- InChI: InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/p-1
- InChIKey: RBNPOMFGQQGHHO-UHFFFAOYSA-M
- IUPAC name: 2,3-dihydroxypropanoate
These identifiers specify the anionic glycerate configuration and are suitable for unambiguous structure exchange and cheminformatics use.
Acid–Base Behavior
Conjugate Acid and Speciation
Glycerate is the conjugate base of glyceric acid (glycerate ⇄ glyceric acid + H+). Speciation in aqueous systems is governed by pH: protonation state, ion pairing with cations, and formation of salts or esters depend on solution conditions. In physiological and neutral aqueous media the carboxylate form predominates, whereas under strongly acidic conditions the protonated carboxylic acid (glyceric acid) becomes more prevalent. The vicinal hydroxyl groups can engage in intramolecular hydrogen bonding to the carboxylate/protonated carboxyl group, affecting conformation and microenvironment acidity.
Acid–Base Equilibria and Qualitative pKa Discussion
No experimentally established value for this property is available in the current data context.
Qualitatively, the presence of alpha (vicinal) hydroxyl substituents can influence the acidity of the carboxyl group via inductive and hydrogen-bonding effects: hydroxyl groups exert modest electron-withdrawing inductive influence and can stabilize certain conformers of the conjugate base through hydrogen bonds. These structural features modulate proton affinity and local microenvironment pKa in enzymes or in nonideal solvents, and they influence salt formation and ion-pairing behavior in mixed solvent systems.
Chemical Reactivity
Chemical Stability
Glycerate is chemically stable under ambient, neutral aqueous conditions typical for biochemical and analytical handling. As an alpha-hydroxy carboxylate, it is less prone to simple hydrolytic cleavage than ester derivatives but can undergo the following class-relevant transformations: - Esterification or formation of acyl derivatives under acidic or activated conditions. - Phosphorylation in biochemical pathways (formation of glycerate-phosphate esters) by kinase enzymes. - Oxidative cleavage or modification of the vicinal diol under strong oxidizing conditions. - Salt formation with common inorganic cations; crystalline salts often demonstrate different hygroscopic and melting behaviour than the free acid.
Care should be taken with strong oxidants or dehydrating agents, which can alter or degrade the vicinal diol functionality.
Formation and Hydrolysis Pathways
Glycerate is commonly formed by oxidation of glycerol or as a downstream metabolite in carbohydrate and glycerol catabolism. In biological systems it is generated and consumed by kinase-, dehydratase-, and dehydrogenase-mediated steps and participates in metabolic flux as an intermediate or waste product. Hydrolytic decomposition of the anion itself is not a primary pathway; however, esterified or activated derivatives (e.g., acyl esters, anhydrides) are susceptible to hydrolysis under acidic or basic conditions. In synthetic or preparative chemistry, glycerate is typically accessed by controlled oxidation of glycerol or isolated as salts following neutralization of glyceric acid.
Identifiers and Synonyms
Registry Numbers and Codes
- CAS number: 383-86-8
Structural and mass identifiers:
- Molecular weight: 105.07
- Exact mass / Monoisotopic mass: 105.01878364
(See the Structural Identifiers section for SMILES, InChI and InChIKey.)
Synonyms and Structural Names
Reported synonyms include:
- Glycerate
- 2,3-dihydroxypropanoate
- aldonates
- aldonate(1-)
Glycerate is functionally described as the conjugate base of glyceric acid and is a member of glycerates and hydroxy monocarboxylate anions.
Industrial and Commercial Applications
Role as Active Ingredient or Intermediate
Glycerate is primarily encountered as an endogenous biochemical intermediate rather than a bulk industrial raw material. In biochemical contexts it serves as a metabolic intermediate in glycerol and carbohydrate catabolism and can be enzymatically phosphorylated or otherwise modified in central metabolic pathways. It is used as a standard or reagent in biochemical and clinical analyses where monitoring of glycerate/glyceric acid levels is relevant.
Representative Application Contexts
Representative application contexts include:
- Biochemical and metabolic research studying glycerol and carbohydrate pathways.
- Clinical diagnostics and biochemical assays related to disorders of glycerate metabolism (e.g., glycerate kinase deficiency, D-glyceric aciduria).
- Use as an analytical standard or reagent in solution-phase assays and method development in analytical chemistry.
No concise application summary is available in the current data context; in practice this substance is selected based on its general properties described above.
Safety and Handling Overview
Toxicity and Biological Effects
Accumulation of glyceric acid/glycerate in biological systems is associated with metabolic disease and toxicity: excessive excretion of glyceric acid is observed in disorders such as D-glyceric aciduria and D-glycerate acidemia, which are linked to enzymatic deficiencies (e.g., glycerate kinase deficiency) and can produce progressive neurological impairment and metabolic disturbances. There is no indication in the current data context of carcinogenicity to humans.
As with many small, highly polar metabolites, systemic toxicity is primarily relevant when endogenous metabolic clearance is impaired or when extraordinarily high concentrations are present; routine laboratory exposure to dilute solutions is of lower acute systemic concern but appropriate precautions remain necessary.
Storage and Handling Considerations
Handle glycerate and its salts with standard laboratory precautions for aqueous organic anions: avoid ingestion, inhalation of dust (for solid salts), and contact with skin and eyes. Use appropriate personal protective equipment (gloves, eye protection, lab coat) and engineering controls (local exhaust, fume hood) when handling powders or concentrated solutions. Protect from strong oxidizing agents and store in a tightly closed container in a cool, dry place away from incompatible substances. For detailed hazard, transport and regulatory information, users should refer to the product-specific Safety Data Sheet (SDS) and local legislation.
