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Beta-D-(-)-arabinose is a reducing sugar, with the chemical formula C5H10O5, CAS 10323-20-3. It is a pentose analog of D-ribose. The white crystal is easily soluble in water, slightly soluble in alcohol, and insoluble in ether, methanol and acetone. It is a component of arabinogalactans in the cell wall of Mycobacterium and a substrate for the synthesis of D-erythroascorbic acid in yeast. it is a five-carbon monosaccharide with the chemical formula C5H10O5, which is a natural product extracted from the fermentation of xylan. Easily soluble in water, but its solubility depends on temperature and concentration. At room temperature, the solubility is about 2.63 g/100 mL. At high concentrations, however, solubility will decrease.
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Chemical Formula |
C5H10O5 |
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Exact Mass |
150 |
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Molecular Weight |
150 |
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m/z |
150 (100.0%), 151 (5.4%), 152 (1.0%) |
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Elemental Analysis |
C, 40.00; H, 6.71; O, 53.28 |
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Conversely, when the temperature increases, the solubility will increase. Its melting point is recorded as 162-165°C in some documents, while 195°C in others. This inconsistency may be due to differences in the origin and purity of the samples used at the time of recording. In fact, this difference also indicates that there may be multiple isomorphs of D-(-)-Arabinose. Is a chiral molecule, it has optical activity. At 20°C, the specific rotation is usually between -104.3° and -104.8°, which means it is left-handed.
Arabinose is a kind of five carbon aldose obtained from the hydrolysis of gum. It usually exists in a binding state in the body. It is a component of various polysaccharides such as gum, hemicellulose, pectin and some glycosides. It predominantly occurs as L-arabinose in natural matrices, rarely appearing in free monomeric form. It participates in cell wall structural construction and regulates carbohydrate metabolic flux, possessing distinctive physiological functions distinct from common hexose saccharides.
There are three optical isomers, mainly L-type, with little difference in most properties, white crystals. Soluble in water and glycerin, insoluble in ethanol and ether. It is used for medicine and culture medium. In addition to being prepared by hydrolyzing the gum from the tree or the cherry tree, it can also be prepared by reacting the dextran calcium gluconate with hydrogen peroxide. Yeast cannot ferment it.L-arabinose is a commonly used food additive, also known as pectinose, L-arabinose, L-Chemicalbook pentose, and its appearance is orthogonal prism crystal at room temperature.
Melting point 159.5 ℃; density α- D2041.585, β- D4201.625; Optical rotation[ α] D20+105 ° (C=3, in water); Very soluble in water, slightly soluble in ethanol, insoluble in ethanol. It can be obtained by partial hydrolysis of mespritegum. Or treat the crushed corn cob with 4% acetic acid at 100 ℃ for 2 hours, separate and wash it, then treat the cob with 1% H2SO4 at 100 ℃, concentrate the hydrolysate, separate it, treat it with charcoal under vacuum, and remove the minerals through ion exchange to obtain 5-5.5% L-arabinose.
It is obtained from calcium gluconate through degradation and oxidation.
The calcium gluconate is heated and dissolved with water, and the barium acetate solution and the ferric sulfate solution are added to form an iron catalyst. Stir and raise the temperature to 95 ℃, and filter out the sediment. The clear solution is oxidized by adding hydrogen peroxide at 40 ℃, and the reaction temperature is not more than 56 ℃, and the reaction lasts for half an hour. After the reaction solution turns black, let it stand for half an hour, cool it to 40 ℃, then add hydrogen peroxide, and oxidize it according to the above method.
After half an hour, add oxalic acid, filter, and remove calcium oxalate. Concentrate the filtrate in vacuum until it is syrupy, and the temperature shall not exceed 48 ℃. Dissolve in anhydrous methanol, cool and crystallize, and filter. Wash the filter cake with methanol and dry it to obtain crude product. The crude product was recrystallized with methanol to obtain D (-) - gum aldose.Another preparation method is to oxidize calcium gluconate and iron gluconate with hydrogen peroxide, filter the reactants and treat them with strong acidic styrene cation exchange resin and strong alkaline quaternary ammonium I anion exchange resin to obtain the finished product.
Beta-D-(-)-arabinose, as a naturally occurring five carbon aldose, has a molecular structure similar to D-ribose and is the core component of arabinogalactan in the cell wall of mycobacteria. It is also a key substrate for the synthesis of D-ascorbic acid in yeast. Its unique chemical properties and biological activity make it widely applicable in fields such as medicine, food, chemical engineering, scientific research, and agriculture.
Medical field: the core role from metabolic regulation to disease treatment
Treatment of metabolic diseases: blood glucose regulation and obesity intervention
D-arabinose significantly reduces the efficiency of sucrose breakdown into glucose and fructose by inhibiting the activity of small intestine sucrase, thereby lowering postprandial blood glucose peak. Clinical trials show that adding 3.5% D-arabinose to sucrose can inhibit the absorption of 60% -70% sucrose in human body. Long term use can improve insulin sensitivity and assist in the treatment of type 2 diabetes. The mechanism is that undigested sucrose enters the large intestine and is fermented by microorganisms to produce short chain fatty acids.
These substances activate intestinal G protein coupled receptors (GPR41/GPR43), promote glucagon like peptide-1 (GLP-1) secretion, further enhance insulin secretion, and inhibit gastric emptying, forming a closed loop of blood glucose regulation.In terms of obesity intervention, D-arabinose works through a dual mechanism: firstly, reducing sucrose absorption directly lowers calorie intake; Secondly, unabsorbed sucrose can inhibit the activity of hepatic fatty acid synthase (FAS) and reduce fat accumulation by producing propionic acid during fermentation in the large intestine.
The "health sugar" (containing 3% D-arabinose) developed by Mitsui Co., Ltd. in Japan has been commercially applied. Clinical data shows that continuous intake for 12 weeks can reduce body fat percentage by 2.3% and waist circumference by 3.1cm in subjects.
Liver protection: synergistic effect of sobering up and antioxidant
D-arabinose can significantly enhance the activity of liver alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH), accelerating alcohol metabolism.
Animal experiments showed that after oral administration of D-arabinose (200mg/kg) to ethanol induced liver injury mice, serum ALT and AST levels decreased by 42% and 38% compared to the model group, liver tissue MDA content decreased by 51%, and SOD activity increased by 67%. The mechanism may involve: NADH produced by D-arabinose metabolism promotes ADH catalyzed oxidation of ethanol to acetaldehyde, while enhancing the conversion efficiency of ALDH to acetaldehyde and reducing oxidative stress damage.
Anti tumor adjuvant therapy: enhancing chemotherapy sensitivity
D-arabinose, as a key intermediate of cytarabine, its metabolite 5-phosphate cytarabine can inhibit DNA polymerase activity and block tumor cell DNA synthesis. In recent years, studies have found that D-arabinose pretreatment can upregulate the sensitivity of leukemia cell line HL-60 to cytarabine, which involves promoting cell cycle arrest in the G1/S phase and increasing chemotherapy drug intake. In addition, D-arabinose derivatives (such as D-arabitol) can pass through the blood-brain barrier and serve as carriers for brain tumor chemotherapy, increasing the concentration of drugs in the central nervous system.
Maintenance of intestinal health: prebiotics and mucosal protection
As a prebiotic, D-arabinose can selectively promote the proliferation of beneficial bacteria such as Bifidobacterium and Lactobacillus, and inhibit the growth of pathogenic bacteria such as Escherichia coli and Salmonella. The fermentation product butyric acid can upregulate the expression of intestinal tight junction proteins (such as ZO-1 and Occludin), enhance intestinal mucosal barrier function, and reduce the risk of endotoxin entering the bloodstream.In addition, D-arabinose inhibits the activation of the NF - κ B pathway, reduces the release of pro-inflammatory factors such as TNF - α and IL-6, and alleviates symptoms of enteritis.
Clinical studies have confirmed that daily supplementation of 5 g D-arabinose can raise the weekly defecation frequency of constipated patients from 2.3 times to 4.1 times, and elevate the water content of feces by 22%. It is not easily digested and absorbed in the small intestine, and can enter the colon to modulate gut microbiota composition, stimulate intestinal peristalsis and improve stool texture without inducing obvious gastrointestinal adverse reactions.
Low calorie sweetener: the core ingredient of diabetes and diet food
D-arabinose has a sweetness of 50% -60% of sucrose, but only 1/10 of its calorie content. After being compounded with sucrose in a ratio of 1:9, its sweetness curve is highly similar to that of pure sucrose, and there is no aftertaste. This feature makes it an ideal choice for sugar free beverages and meal replacements. For example, a certain brand of sugar free yogurt reduces its calorie intake from 85kcal/100g of traditional products to 42kcal/100g by adding 0.5% D-arabinose while maintaining its sweetness.
Food preservation and texture improvement: multifunctional food additives
D-arabinose undergoes Maillard reaction with amino groups in protein molecules to generate brown pigments with antioxidant activity, which can extend the shelf life of meat products.In baked goods, beta-D-(-)-arabinose forms hydrogen bonds with starch molecules, inhibits starch retrogradation, increases bread softness by 30%, and reduces aging rate by 45%. In addition, the moisturizing properties of D-arabinose make it a high-quality base material for chewing gum and gummies, which can prevent the product from hardening and cracking.
Food Safety Assurance: Natural Shielding Agents for Heavy Metal Pollution The adjacent hydroxyl groups within D-arabinose molecules are capable of forming stable chelates with heavy metal ions including Pb²⁺ and Cd²⁺, lowering their migration rate in food matrices. Experiments have demonstrated that supplementation of 0.2% D-arabinose into simulated food systems containing 10 mg/kg lead achieves a lead ion chelating rate of 92%, which substantially cuts down the hazards arising from heavy metal intake by humans. This chelation relies on coordinate bond interaction,lessening their accumulation in human visceral tissues, which outperforms many synthetic chelators in biocompatibility.
Chemical industry: key raw materials from material synthesis to industrial optimization
Polymer material modification: innovative application of functional additives
D-arabinose derivatives (such as arabinose anhydrides) can be used as chain extenders for epoxy resins and polyurethanes, introducing active groups such as hydroxyl and carboxyl groups to enhance the hydrophilicity and biodegradability of the materials. For example, adding 5% arabic anhydride to polylactic acid film reduces the water contact angle from 92 ° to 68 ° and increases the degradation rate from 12% to 37% in 60 days.
Performance improvement of capacitors: breakthrough in electrolyte additives
In aluminum electrolytic capacitors, D-arabitol as a solute can significantly increase the viscosity of the electrolyte (from 1.2mPa · s to 2.8mPa · s) and reduce the corrosion rate of aluminum foil.Meanwhile, its multi hydroxyl structure can form complexes with aluminum ions, inhibiting the growth of aluminum dendrites and extending the lifespan of capacitors by 40%. The products of a certain enterprise using this technology have passed the vehicle specification level certification, and the working temperature range has been expanded to -55 ℃~150 ℃.
Stability of developing materials: optimization of photosensitive system D-arabinose, as a stabilizer for silver salt developer, can chelate metal ions (such as Fe³⁺) in the developer, inhibit oxidative side reactions, and prolong the service life of the developer. Experimental data shows that adding 0.5% D-arabinose to the developing solution increases the effective development times from 15 times to 28 times, and the image contrast is improved by 12%. The polyhydroxy structure of D-arabinose can also scavenge free radicals generated during the redox reaction of silver ions, slowing down the spontaneous degradation of active developing components.
Compared with traditional organic stabilizers, it exhibits lower interference with silver halide nucleation. This provides a green alternative strategy to enhance the recyclability and working stability of silver salt photosensitive developing systems. It hardly introduces extra chromatic impurities during imaging procedures and maintains the intrinsic spectral response characteristics of silver halide emulsions. Furthermore, it possesses favorable solubility under weakly alkaline developing conditions and avoids sediment formation after long-term circulation, overcoming many drawbacks of conventional phenolic stabilizers used in photosensitive materials.
Research field: Diversified support from standard materials to model tools
Biochemical standards: benchmarks for quantitative analysis D-arabinose primary standard (purity ≥ 99.9%) is certified by NBS (National Bureau of Standards) and used to calibrate decisive analytical methods such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR). The impurity content (such as D-xylose and L-arabinose) is accurately determined by quantitative nuclear magnetic resonance (qNMR) with an uncertainty of less than 0.05%, providing a reliable reference for the analysis of carbohydrate compounds.
Microbial culture medium: Specific nutrient supplementation As a core component of culture media for Mycobacterium tuberculosis, D-arabinose provides essential monomers for the synthesis of arabinogalactan.Adding 0.02% D-arabinose to Middlebrook 7H9 medium can increase the colony forming units (CFU) of Mycobacterium tuberculosis H37Rv strain by 2.3 times and shorten the culture period by 3 days.
Metabolic pathway research: tools for model organisms In the Caenorhabditis elegans model, D-arabinose extended nematode lifespan by 18% by activating the DAF-16/FOXO transcription factor. This discovery provides a new perspective for the study of aging mechanisms, and the related results were published in Nature Aging (2024). In addition, D-arabinose, as a substrate for yeast D-ascorbic acid synthesis, is widely used in redox equilibrium studies.
Plant growth regulation: dual roles of carbon sources and signaling molecules D-arabinose, as a hydrolysis product of plant hemicellulose, can be directly absorbed and utilized by roots. It promotes lateral root formation by upregulating the expression of key enzymes involved in auxin (IAA) synthesis, such as YUCCA6. In tomato seedling experiments, foliar spraying of 0.1% D-arabinose solution can increase root biomass by 27% and plant height by 19%.
Soil remediation: heavy metal passivation and microbial regulation D-arabinose reduces its bioavailability by forming insoluble complexes with Cd ² ⁺ and Cu ² ⁺ in the soil. Applying biochar containing 2% D-arabinose in cadmium contaminated farmland (Cd content 3.2mg/kg) can reduce cadmium accumulation in rice grains by 61%. At the same time, as a carbon source, it can stimulate a 35% increase in soil actinomycete abundance and enhance the ability of microorganisms to degrade organic pollutants.
Beta-D-(-)-arabinose, with its unique chemical structure and biological activity, has expanded from traditional scientific research reagents to billion dollar markets such as pharmaceuticals, food, and chemicals. With the breakthrough of synthetic biology technology (such as the yeast cell factory's D-arabinose production reaching 120g/L), its production cost has been reduced by 60% compared to chemical synthesis methods, laying the foundation for large-scale applications.
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