CAS 58-86-6 Xylose - Analytical Products / Alfa Chemistry

CAT	APS58866A
CAS	58-86-6
Structure
MDL Number	MFCD00064360
Synonyms	D-(+)-Xylose, Xylose, Wood sugar, Xylose, D- (8CI), (+)-Xylose,D-Xylose, (+)-d-Xylopyranose
IUPAC Name	(2R,3S,4R)-2,3,4,5-tetrahydroxypentanal
Molecular Weight	150.13
Molecular Formula	C5H10O5
Canonical SMILES	OC[C@@H](O)[C@H](O)[C@@H](O)C=O
InChI	InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5+/m0/s1
InChI Key	SRBFZHDQGSBBOR-IOVATXLUSA-N
REAXYS Number	1562108

Description	United States Pharmacopeia (USP) Reference Standard
Accurate Mass	150.0528
API Family	Matrix - API Family See respective official monograph(s)
Format	Neat
MP	154-158 °C (lit.)
Shipping	Room Temperature
Size	1G
Storage Conditions	2-8°C Fridge/Coldroom
Subcategory	European Pharmacopoeia (Ph. Eur.)
Type	Excipient

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Case Study

Xylose Used for Maillard-Type Time-Temperature Indicator (TTI) in Seafood Shelf-Life Monitoring

Ye, Beibei, et al. Journal of Food Engineering 355 (2023): 111583.

Xylose was utilized to construct a Maillard reaction-based time-temperature indicator (TTI) for monitoring the freshness of large yellow croakers. The experimental procedure was conducted as follows:
1. Preparation of Solutions: D-xylose (1.0 M) and L-lysine (2.0 M) were individually dissolved in phosphate-buffered saline (0.15 M, pH 7.0).
2. Reaction System Assembly: Equal volumes (200 μL each) of xylose and lysine solutions were mixed in a 1:1 ratio (v/v) to form the Maillard reaction system.
3. TTI Device Fabrication: The reaction mixture was encapsulated in high-transmitting composite films composed of o-phenylphenol and cast polypropylene, producing devices of dimensions 20 mm × 25 mm × 1 mm.
4. Application and Monitoring: TTIs were attached to the surface of seafood samples stored at temperatures ranging from 0 to 25 °C. Color changes were recorded using UV-visible spectroscopy to assess the progression of the Maillard reaction.
5. Kinetic Analysis: The activation energy (Ea) of the TTI response (83.51 kJ/mol) was compared with total volatile basic nitrogen (TVB-N, 70.45 kJ/mol). Effective temperatures (Teff) and shelf-life predictions were calculated to evaluate the TTI accuracy under fluctuating storage conditions.
The results demonstrated that xylose-based TTIs provide an accurate, environmentally friendly, and visually intuitive method for real-time seafood quality assessment, enabling precise monitoring of spoilage kinetics in cold chain logistics.

Xylose Used for the Preparation of Hierarchically Porous Carbon Microspheres for Supercapacitor Applications

Waribam, Preeti, et al. Waste Management 105 (2020): 492-500.

Xylose was employed as a carbon precursor for the fabrication of activated carbon microspheres (mCMs) with controllable porous structures and high electrochemical performance. The experimental procedure was conducted as follows:
1. Hydrothermal Carbonization: Fifteen grams of xylose were dissolved in 30 mL of deionized water and transferred into a 150 mL Teflon-lined stainless-steel autoclave. The autoclave was heated at 190 °C for 24 h under autogenous pressure to yield carbon microspheres (CMs).
2. Washing and Drying: The resulting CMs were sequentially washed with 250 mL of ethanol and deionized water until neutral pH was reached, followed by drying at 70 °C for 12 h.
3. Sequential Chemical Activation: CMs underwent KOH activation to generate initial porosity, followed by H3PO4 treatment to further enlarge pores and introduce surface phosphorous groups. Key parameters, including KOH:C and H3PO4:C molar ratios, H3PO4 heating rate, and activation time, were systematically varied to optimize pore size and distribution.
4. Characterization and Application: The activated mCMs retained their spherical morphology with a nearly 700-fold increase in surface area compared to non-activated CMs. Phosphorus-functionalized surfaces enhanced electrochemical performance, achieving a maximum specific capacitance of 277 F g-1 and a power density of 173.88 W kg-1 as a supercapacitor electrode.
This study demonstrates that xylose is an effective, sustainable precursor for the preparation of hierarchically porous carbon materials. The combined hydrothermal carbonization and sequential KOH-H3PO4 activation strategy enables precise control over pore architecture and surface chemistry, yielding high-performance carbon microspheres suitable for energy storage applications.

Xylose Used for High-Yield Chondroitin Production via Engineered Corynebacterium glutamicum

Shi, Zhuangzhuang, et al. International Journal of Biological Macromolecules (2025): 147392.

Xylose was employed as a renewable carbon source for the biosynthesis of chondroitin, a precursor of chondroitin sulfate, in engineered Corynebacterium glutamicum. The experimental workflow was conducted as follows:
1. Strain Engineering: Genes encoding chondroitin synthase (KfoC) and UDP-N-acetylglucosamine-4-epimerase (KfoA) were codon-optimized and introduced into C. glutamicum. Metabolic pathways and medium components were tailored to maximize chondroitin synthesis, yielding the high-titer strain CgC25.
2. Xylose Metabolism Optimization: Xylose utilization pathways, including xylose isomerase (XI) and Weimberg routes, were reconstructed using an RBS-library strategy to generate strain CgRXIW, capable of efficient xylose conversion.
3. Medium Preparation and Fermentation: C. glutamicum strains were cultured in optimized media containing both glucose and xylose derived from corn stover hydrolysate. Fermentation parameters, including carbon source concentration, corn steep powder, and nutrient supplementation, were systematically adjusted to enhance product yield. Antibiotics (kanamycin, chloramphenicol) and IPTG were applied as needed for gene induction.
4. Production Assessment: Fed-batch fermentation of engineered strains achieved a chondroitin titer of 9.59 ± 0.15 g/L from glucose, and 6.64 ± 0.11 g/L from corn stover hydrolysate, demonstrating effective co-utilization of glucose and xylose.
This study highlights xylose as a sustainable and versatile feedstock for the cost-effective biosynthesis of high-value biopolymers. Integration of xylose metabolism with chondroitin synthesis modules establishes a scalable platform for producing chondroitin from lignocellulosic biomass, providing a strategic route for industrial biomanufacturing of biomedical compounds.