D-Erythrose (583-50-6) Physical and Chemical Properties
D-Erythrose
A four-carbon aldo-sugar used as an analytical reference standard and research intermediate in carbohydrate metabolism and synthetic chemistry.
| CAS Number | 583-50-6 |
| Family | Monosaccharide (aldose) |
| Typical Form | Crystalline solid or aqueous solution |
| Common Grades | EP |
D‑Erythrose is an aldotetrose — a four‑carbon monosaccharide in the aldose structural class — bearing three vicinal hydroxyl groups and a terminal aldehyde. The free (open‑chain) form contains an aldehyde at C‑1 and hydroxyls at C‑2, C‑3 and C‑4; the molecule contains two defined stereocenters (configuration (2R,3R) for the D‑enantiomer) and readily equilibrates with intramolecular hemiacetal (cyclic) forms typical of small aldoses. Electronically it is highly polarized owing to the dense array of hydroxyl substituents and the aldehyde function; strong hydrogen‑bonding capacity governs intermolecular interactions and solid‑state packing.
The combination of a terminal aldehyde and multiple hydroxyls confers typical reducing‑sugar reactivity (oxidation to the corresponding aldonic/aldaric acids, participation in redox tests and conjugation reactions) and acid/base sensitivity (acid‑catalyzed dehydration and base‑catalyzed enediolization/isomerization). Physicochemically the molecule is strongly hydrophilic with low intrinsic lipophilicity (computed XLogP = -2.2) and a large polar surface area, which predict high aqueous solubility, limited passive membrane permeability, and strong solvation by protic solvents. Thermal instability and polymerization or browning (dehydration/condensation) are common for small aldoses upon heating or prolonged storage in impure or acidic media.
D‑Erythrose is encountered as a primary metabolite or intermediate in biological systems (reported in plants and microorganisms) and is used in biochemical research and carbohydrate chemistry as a chiral building block and analytical standard. 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
No experimentally established value for this property is available in the current data context.
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
D‑Erythrose is a small, highly polar carbohydrate expected to be highly soluble in water and other polar protic solvents and essentially insoluble in nonpolar organic solvents. In aqueous solution the open‑chain aldehyde form exists in equilibrium with intramolecular hemiacetal (cyclic) forms; this equilibrium and extensive hydrogen bonding control phase behavior, colligative properties, and crystallization tendencies. No quantitative solubility values are provided in the current data context.
Reactivity and Stability
Chemically, D‑erythrose behaves as a typical reducing aldose. The aldehyde group is susceptible to facile oxidation (to the corresponding erythronic acid and related oxidation products) and to nucleophilic addition; the compound will give positive reactions in standard reducing‑sugar tests. Under basic conditions aldoses can undergo enediolization and isomerization to ketoses or epimerize at adjacent stereocenters. Under acidic or high‑temperature conditions dehydration, polymerization and Maillard‑type browning reactions may occur, leading to oligomers and colored degradation products. Storage in damp, warm, or impure conditions accelerates decomposition; stabilization typically requires low temperature, exclusion of strong acids/bases and avoidance of prolonged exposure to air and light.
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: C4H8O4
- Molecular weight: \(120.10\,\mathrm{g}\,\mathrm{mol}^{-1}\)
- Exact mass: 120.04225873
- Monoisotopic mass: 120.04225873
LogP and Polarity
- XLogP3 (computed): -2.2
- Topological polar surface area (TPSA): \(77.8\,\text{Å}^2\)
- Hydrogen bond donor count: 3
- Hydrogen bond acceptor count: 4
- Rotatable bond count: 3
These computed parameters are consistent with a strongly hydrophilic molecule with limited lipophilicity and high potential for hydrogen bonding; such properties predict favorable aqueous solubility and limited passive diffusion across hydrophobic membranes.
Structural Features
- Functional groups: terminal aldehyde (aldose) and three secondary/primary hydroxyl groups.
- Stereochemistry: two defined stereocenters (reported configuration (2R,3R)).
- SMILES: C(C@HO)O
The molecule readily forms intramolecular hemiacetals (cyclic ring forms) in solution, and exists as an equilibrating mixture of open‑chain and cyclic isomers typical of small reducing sugars.
Identifiers and Synonyms
Registry Numbers and Codes
- CAS Number: 583-50-6
- Alternative CAS / deprecated CAS entries shown in source materials: 1758-51-6; deprecated: 29825-68-1; 210230-59-4
- EC number: 209-505-2
- UNII: X3EI0WE8Q4; 756EZ12FT6
- InChI: InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1
- InChIKey: YTBSYETUWUMLBZ-IUYQGCFVSA-N
- SMILES: C(C@HO)O
(Identifiers above are drawn from the documented registry and computational descriptor fields.)
Synonyms and Structural Names
Representative synonyms and names reported in source lists include (strings shown exactly as provided):
- D-Erythrose
- D-(-)-Erythrose
- (2R,3R)-2,3,4-trihydroxybutanal
- D-erythro-tetrose
- Erythrose, D-
- D-Erythrose (w/v = 10 mg/ml)
- Butanal, 2,3,4-trihydroxy-, (2R,3R)-rel-
- D-Erythrose, 70% aqueous solution
(Additional vendor, catalog and registry synonyms are present in source material; the above are representative strings.)
Industrial and Commercial Applications
Representative Uses and Industry Sectors
D‑Erythrose is primarily encountered in biochemical, metabolic and research contexts as a naturally occurring metabolite in plants and microorganisms. It is used as an analytical standard, as a reagent/intermediate in carbohydrate chemistry, and in studies of sugar reactivity and stereochemistry. There is no specific niche industrial commodity application listed in the current data context beyond these laboratory, research and biochemical roles.
Role in Synthesis or Formulations
As a chiral aldotetrose, D‑erythrose serves as a building block and substrate in synthetic carbohydrate chemistry, stereoselective transformations and method development for sugar derivatization. It can be used to prepare protected sugar derivatives, as a precursor for oxidation/reduction chemistry, and as a model reducing sugar in analytical method validation. In formulations it is mainly relevant where reducing‑sugar chemistry or carbohydrate‑mediated reactivity is required.
Safety and Handling Overview
Acute and Occupational Toxicity
GHS hazard information reported for concentrated material indicates:
- Signal word: Warning
- GHS hazard statements (as reported): H315 (100%): Causes skin irritation; H319 (100%): Causes serious eye irritation; H335 (100%): May cause respiratory irritation.
- Hazard classes/categories reported: Skin Irrit. 2 (100%); Eye Irrit. 2 (100%); STOT SE 3 (100%).
Precautionary statement codes provided in source listings include: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501.
No experimentally established numeric acute toxicity values (e.g., LD50, LC50) are available in the current data context.
Storage and Handling Considerations
Handle D‑erythrose using standard precautions appropriate for powdered or concentrated carbohydrate materials: avoid inhalation of dust and contact with eyes and skin, use appropriate personal protective equipment (gloves, eye protection, and respiratory protection if dust may be generated), and minimize dust formation. Store in tightly closed containers in a cool, well‑ventilated area away from strong oxidizing agents; protect from prolonged exposure to heat and moisture to reduce thermal decomposition and microbial growth. For detailed hazard, transport and regulatory information, users should refer to the product‑specific Safety Data Sheet (SDS) and local legislation.
