sn-Glycerol 3-phosphate (17989-41-2) Physical and Chemical Properties
sn-Glycerol 3-phosphate
A phosphorylated glycerol derivative used as a biochemical reagent and analytical standard for metabolomics, enzymology and formulation R&D.
| CAS Number | 17989-41-2 |
| Family | Glycerol phosphates |
| Typical Form | Powder or crystalline solid |
| Common Grades | EP |
sn-Glycerol 3-phosphate is a small, highly polar organophosphate belonging to the sn-glycerol 3-phosphates (glycerol monophosphate) structural class. The molecule is a monoester of phosphoric acid linked to a glycerol backbone: a phosphate dihydrogen ester attached to a 1,2,3-propanetriol unit with vicinal secondary and primary hydroxyl groups. The defined stereochemistry at the central carbon yields the (2R) enantiomer in the sn (stereospecific numbering) configuration; the preferred IUPAC description is [(2R)-2,3-dihydroxypropyl] dihydrogen phosphate. Key electronic features include a highly polarized phosphate monoester (strong hydrogen-bond acceptor/donor capacity in its protonation states) and multiple hydroxyl functions that increase aqueous solvation and hydrogen-bonding networks.
As a consequence of its functional groups, the compound is strongly hydrophilic and displays very low lipophilicity (XLogP \(-2.9\)). Acid–base behavior is dominated by the phosphate moiety: under physiological conditions the species exists largely in deprotonated anionic forms (conjugate acid/base relationships typical of phosphate monoesters), while the neutral stereochemical backbone imparts no formal covalent charge. Hydrolytic cleavage of the phosphate ester is kinetically controlled under neutral conditions but can be catalyzed by acids, bases, or phosphatases enzymatically; oxidative degradation is not a primary pathway for this scaffold. Sulfide- or nitro-type reactivity is absent; the compound is chemically stable as a crystalline solid under ambient, dry conditions.
This compound is a ubiquitous metabolic intermediate in central carbon and lipid metabolism and is detected in multiple organisms and tissues; it participates in pathways such as cardiolipin biosynthesis and is commonly encountered in biochemical and metabolomics workflows. Common commercial grades reported for this substance include: EP.
Basic Physical Properties
Density
No experimentally established value for this property is available in the current data context.
Melting Point
Experimental melting point: \(102 - 104\,^\circ\mathrm{C}\). The substance is reported as a solid; the relatively low melting point for a polar phosphate monoester reflects limited lattice stabilization typical of small, hydrogen-bonded crystalline organics.
Boiling Point
No experimentally established value for this property is available in the current data context.
Vapor Pressure
No experimentally established value for this property is available in the current data context.
Flash Point
No experimentally established value for this property is available in the current data context.
Chemical Properties
Solubility and Phase Behavior
Experimental solubility is reported as \(1000.0\,\mathrm{mg}\,\mathrm{mL}^{-1}\), indicating very high aqueous solubility consistent with multiple hydroxyl groups and a phosphate monoester. Phase behavior for such small, highly polar solids typically shows good miscibility with water across a wide concentration range; organic solvent solubility is expected to be very limited except in highly polar protic solvents. In solution, extensive hydrogen-bonding and ionization of the phosphate group lead to strong solvation and formation of hydrated anionic species under neutral to basic pH.
Reactivity and Stability
Under neutral, dry storage the molecule is chemically stable as a solid. The phosphate ester can undergo enzymatic hydrolysis (phosphatases) and can hydrolyze chemically under strongly acidic or basic conditions; therefore aqueous stability is pH-dependent. The absence of redox-active substituents limits oxidative reactivity under normal handling conditions. Compatibility issues: avoid strong dehydrating agents that could promote condensation or polymerization of phosphate-containing species, and avoid strong nucleophiles or bases that accelerate ester cleavage. Thermal decomposition profiles are not provided here; refer to product-specific analytical data for elevated-temperature processing.
Thermodynamic Data
Standard Enthalpies and Heat Capacity
No experimentally established value for this property is available in the current data context.
Molecular Parameters
Molecular Weight and Formula
- Molecular formula: C3H9O6P
- Molecular weight: \(172.07\,\mathrm{g}\,\mathrm{mol}^{-1}\)
- Exact mass: \(172.01367500\) (reported)
- Monoisotopic mass: \(172.01367500\) (reported)
The small molar mass and multiple oxygen atoms contribute to high polarity and a large hydration shell in aqueous media.
LogP and Polarity
- XLogP (computed): \(-2.9\)
- Topological polar surface area (TPSA): \(107\ \text{Å}^2\)
- Hydrogen bond donors: 4
- Hydrogen bond acceptors: 6
These parameters indicate strong aqueous affinity, low membrane permeability in the neutral/ionic mixture, and significant capability for hydrogen-bond mediated interactions with proteins and solvent. High TPSA and low XLogP predict limited passive diffusion across lipid bilayers; transport in biological systems is typically carrier-mediated.
Structural Features
The molecule contains a glycerol backbone bearing a phosphate dihydrogen ester at the primary (sn-1) position and vicinal hydroxyls at the remaining carbons; the structure includes a single defined stereocenter (configured as (2R) in the sn nomenclature). Functional groups and structural motifs: phosphate monoester (acidic, ionizable), two secondary/primary alcohols capable of hydrogen bonding, and a flexible three-carbon chain with up to four rotatable bonds. The molecule commonly exists as deprotonated anionic species in physiological media and forms salts with cations (e.g., sodium) for many commercial reagents.
Identifiers and Synonyms
Registry Numbers and Codes
- CAS: 17989-41-2
- Alternative CAS reported in some sources: 57-03-4 (appears in identifier lists)
- UNII: 370V52HE4B
- ChEBI: CHEBI:15978
- ChEMBL: CHEMBL1232920
- DrugBank: DB02515
- DSSTox Substance ID: DTXSID5048346
- HMDB: HMDB0000126
- KEGG: C00093
- Nikkaji Number: J4.456C
- Wikidata: Q27093499
- InChI: InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1
- InChIKey: AWUCVROLDVIAJX-GSVOUGTGSA-N
- SMILES: C(C@HO)O
(When using structural identifiers in informatics workflows, the plain InChI, InChIKey and SMILES strings above should be used as provided.)
Synonyms and Structural Names
Depositor-supplied synonyms include (exact strings preserved):
sn-Glycerol 3-phosphate; 17989-41-2; D-Glycerol 1-phosphate; (R)-glycerol 1-phosphate; Glyceryl 1-phosphate, (R)-; Glycerol, 1-(dihydrogen phosphate), d-; 370V52HE4B; D-(glycerol 1-phosphate); L-(glycerol 3-phosphate); CHEBI:15978; 1,2,3-Propanetriol, 1-(dihydrogen phosphate), (R)-; 1,2,3-Propanetriol, 1-(dihydrogen phosphate), (2R)-; DTXSID5048346; phosphoric acid mono-((R)-2,3-dihydroxy-propyl) ester; RefChem:886478; GlyTouCan:G89289AE; DTXCID0028321; G89289AE; sn-Glycero-3-phosphate; sn-glycerol-3-phosphate; [R,(-)]-1-O-Phosphono-D-glycerol; [(2R)-2,3-dihydroxypropyl] dihydrogen phosphate; UNII-370V52HE4B; Glycerol monophosphate; glycerol-3-phosphate; (R)-2,3-Dihydroxypropyl dihydrogen phosphate; (2R)-2,3-dihydroxypropyl dihydrogen phosphate; GLYCEROPHOSPHATE; Glycerophosphoric acid I; C3H9O6P; a-Phosphoglycerol; Glycerophosphorate; a-Glycerophosphate; a-Glycerophosphorate; 1-Glycerophosphorate; Glycerol a-phosphate; DL-a-Glycerophosphate; alpha-Glycerophosphorate; DL-a-Glycerophosphorate; a-Glycerophosphoric acid; DL-a-Glycerol phosphate; DL-a-Glyceryl phosphate; DL-alpha-Glycerophosphate; (R)-glyceryl 1-phosphate; DL-alpha-Glycerophosphorate; DL-a-Glycerophosphoric acid; DL-alpha-Glycerol phosphate; DL-alpha-Glyceryl phosphate; dihydrogen a-glycerophosphate; SCHEMBL213379; DL-alpha-Glycerophosphoric acid; orb1706182; SCHEMBL3340890; CHEMBL1232920; AWUCVROLDVIAJX-GSVOUGTGSA-N; 1-(dihydrogen phosphate) Glycerol; MFCD00236373; sn-glycerol 3-(dihydrogen phosphate); AKOS006273069; DB02515; HY-113128; [(2R)-2,3-dihydroxypropoxy]phosphonic acid; CS-0059649; GLYCEROPHOSPHORIC ACID D-.ALPHA.-FORM; NS00069352; C00093; GLYCEROPHOSPHORIC ACID D-.ALPHA.-FORM [MI]; Phosphorsaeure-mono-((R)-2,3-dihydroxy-propylester); Q27093499
(Selected synonyms are useful for procurement, inventory mapping and interoperability between nomenclature systems; exact strings above reflect source synonym lists.)
Industrial and Commercial Applications
Representative Uses and Industry Sectors
sn-Glycerol 3-phosphate is principally important as a biochemical intermediate and analytical reference standard. It is widely encountered in research, diagnostic and metabolomics laboratories where it serves as a metabolite marker and as a reagent for studying glycerophospholipid metabolism and energy pathways (for example, involvement in cardiolipin biosynthesis). The compound is relevant in pharmaceutical and biotechnology research contexts as a substrate, ligand, or standard in enzyme assays and mass-spectrometry–based metabolite profiling.
Role in Synthesis or Formulations
In synthetic and formulation contexts it is used primarily as a reagent or standard rather than a bulk solvent or excipient. Typical uses include enzyme assays (substrate or product standards), calibration standards for LC–MS/MS and GC–MS metabolomics workflows, and as a building block or intermediate in biochemical studies of glycerophosphate-dependent pathways. Because of its high polarity and ionic behavior, it is not commonly used as a formulation excipient for lipophilic drug delivery without prior chemical modification or salt formation.
Safety and Handling Overview
Acute and Occupational Toxicity
No experimentally established LD50 or specific acute toxicity numeric values for this compound are available in the current data context. As a small, non-volatile, highly polar phosphate monoester present in biological systems, the compound is not expected to present the same acute hazards as volatile organic solvents or strong corrosives; however, direct exposure by ingestion, inhalation of dust, or prolonged skin contact should be minimized. Standard laboratory occupational controls are recommended: use of gloves, eye protection, and good ventilation or local exhaust for dust-generating operations. Avoid ingestion and eye contact.
Storage and Handling Considerations
Store as a dry solid in a tightly closed container, protected from prolonged exposure to moisture and extremes of temperature. Because aqueous solutions can support hydrolysis and microbial growth, store prepared solutions refrigerated and use within validated holding times; adjust pH and include preservatives as appropriate for long-term aqueous storage if permitted by intended use. Handle under standard laboratory safety procedures: avoid generating dust, maintain cleanliness to prevent cross-contamination with analytical samples, and segregate from strong oxidizers and strong bases/acids that may catalyze degradation. For detailed hazard, transport and regulatory information, users should refer to the product-specific Safety Data Sheet (SDS) and local legislation.
