488-82-4

Usage

Uses

1. Used in Enzyme Research:
D-Arabinitol is used as a substrate for identifying, differentiating, and characterizing enzymes such as gluconobacter oxydans dehydrogenase(s), Gox2181, hyperthermophilic D-arabitol dehydrogenase from Thermotoga maritime, and NAD-dependent D-arabitol dehydrogenase from acetic acid bacterium, Acetobacter suboxydans.
2. Used in Biotechnology for Diagnostics:
D-Arabinitol is used as a diagnostic marker in the detection of invasive candidosis. The approach involves measuring D-arabinitol concentrations in human serum or urine, which are produced by most medically important Candida species. Various methods, including enzymatic-fluorometric and enzymatic-colorimetric procedures, have been developed for this purpose. The results are reported as the D-arabinitol-creatinine ratio, which can help in the early detection of invasive Candidiasis.
3. Used in Occurrence and Formation Studies:
D-Arabinitol is found in various natural sources and can be formed through different processes such as fermentation of glucose and in 40% yields using blackstrap molasses. It is also formed by catalytic hydrogenation of D-arabinose in the presence of Raney nickel and from the γ-lactones of D-arabinonic and D-lyxonic acids by reduction with sodium borohydride.
4. Used in Chemical Properties Research:
D-Arabinitol's chemical properties as a white to off-white fine crystalline powder make it a subject of interest for research in chemical properties and potential applications in various industries.

Purification Methods

This pentol, which occurs in lichens and fungi, is purified by recrystallisation from 90% EtOH or MeOH. [Ashina & Yamagita Chem Ber 67 801 1934, derivarives: Nakagawa et al. Bull Chem Soc Jpn 40 2150 1967, Prince & Reichstein Helv Chim Acta 20 101 1937, Hough & Theobald Methods in Carbohydrate Chemistry I 94 1962, Academic Press, Beilstein 1 IV 2832.]

InChI:InChI=1/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1

Upstream product

• 10323-20-3 D-Arabinose 
• 1114-34-7 D-lyxose 
• 2280-44-6 D-Glucose 
• 154-17-6 D-2-deoxyglucose 
• 3445-24-7 D-erythro-pentos-2-ulose 
• 5729-75-9 3-deoxy-D-gluconic acid 
• 81076-14-4 (1'R,2R,3S)-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-propane-1,2,3-triol 
• 114675-40-0 (R)-2-((4S,5R)-5-Methoxymethoxy-2,2-dimethyl-[1,3]dioxan-4-yl)-1,4-dioxa-spiro[4.5]decane 
• 24822-33-1 D-isomaltose 
• 536-11-8 gentibiose 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 488-30-2 arabinoic acid 
• 141-46-8 Glycolaldehyde 
• 56-82-6 Glyceraldehyde 

Downstream Products

• 119248-59-8 pentakis-O-(2,4-dinitro-phenyl)-D-arabitol 
• 80924-06-7 1,3-O-benzylidene D-arabitol 
• 5329-57-7 1.5-dibenzoyloxy-D-arabino-pentanetriol-(2.3.4) 
• 488-84-6 D-ribulose 
• 26293-27-6 trifluoroacetylated arabinitol 
• 5346-78-1 D-arabinitol pentaacetate 
• 5346-78-1 1,2,3,4,5-penta-O-acetyl-DL-arabinitol 
• 7208-42-6 penta-O-acetylribitol 
• 3325-26-6 1,4-anhydroarabinitol 2,3,5-triacetate 
• 3325-26-6 syn-2-(acetoxymethyl)-3,4-diacetoxytetrahydrofuran 
• 5346-78-1 penta-O-acetyl-xylitol 
• 3325-26-6 2,3,5-tri-O-acetyl-1,4-anhydro-DL-xylitol 
• 14227-76-0 1,5-anhydroarabinitol 2,3,4-triacetate 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 

Relevant academic research and scientific papers

Continuous transfer hydrogenation of sugars to alditols with bioderived donors over Cu-Ni-Al catalysts

The transfer hydrogenation of sugars to alditols with biobased alcohol donors was studied over hydrotalcite-derived Cu6-xNixAl2 catalysts prepared by coprecipitation at different pH and featuring variable Cu/Ni ratios. Their evaluation, after in situ activation in pure H2 at 773 K, in the ethanol-assisted upgrading of glucose in a continuous-flow fixed-bed reactor identified the solid synthesized at pH 9-10 and with Cu/Ni=1 as the best performer. Based on textural, structural, and redox analyses, this is related to an enhanced intermetallic interaction. Upon screening alternative donors, a sorbitol yield as high as 67 % was achieved with 1,4-butanediol. The catalytic system displayed a stable behavior during 48 h on stream and proved suitable to hydrogenate also fructose, mannose, xylose, and arabinose to the corresponding polyols (yields up to 65 %), thus standing as a more sustainable and economical alternative to Ru-based catalysts for sugar reductive upgrading. Finding the right partner: Hydrotalcite-derived Cu-Ni-Al materials efficiently catalyze the continuous transfer hydrogenation of C6 and C5 sugars with biobased alcohols as hydrogen donors with yields of up to 67 %. This technology comprises a safer and cheaper alternative to direct hydrogenation over Ru catalysts.

Efficient Synthesis of Sugar Alcohols over a Synergistic and Sustainable Catalyst

A series of catalysts were prepared for sugar alcohols production to overcome the deficiencies of the previous reported catalysts, such as low yield of sugar alcohols, single function, instability, and controversial role of active sites. The role of each metal and their synergistic-cooperation was discussed in detail with a combination of conditional experiments and characterizations. The results indicated that bifunctional Ni6.66Fe1Al1.55 catalyst has unique structure with superparamagnetism and excellent activity. The (111) and (200) planes of metallic Ni are the hydrogenation active phases and preferentially exposed on Ni-Al-Ox spinel. The desired arabitol or mannitol was obtained by tuning the ratio of Br?nsted and Lewis acid sites. The recycling tests indicated that the unique structure of the prepared Ni-based catalyst can suppress leaching and poisoning, which has high textural stability and activity.

Room temperature versatile conversion of biomass-derived compounds by means of supported TiO2 photocatalysts

The selective oxidation of glucose and degradation of phenol in liquid phase were studied in the presence of supported TiO2 photocatalysts. Photocatalysts were synthesized by a modified ultrasound-assisted sol-gel method. The fact of supporting TiO2 on zeolite type Y is giving more selective photocatalyst in glucose oxidation toward glucaric acid (GUA) and gluconic acid (GA) (total selectivity approx. 68%, after 10 min illumination time and 50%H2O/50%acetonitrile solvent composition) than the unsupported TiO2 and the commercially available photocatalyst Evonik P-25. Photocatalysts worked at room temperature, atmospheric pressure and very short reaction times (up to 15 min). Additionally, these photocatalysts were investigated in the mineralization of phenol as a cellulosic industries water contaminant. It was observed that fumed silica is a better option than zeolite as titania support in phenol aqueous degradation. Ultrasound-promoted sol-gel methodology is giving promising supported TiO2 photocatalysts for water purification and solar chemicals production.

Ruthenium nanoparticles supported on zeolite y as an efficient catalyst for selective hydrogenation of xylose to xylitol

Zeolite Y (HYZ) supported ruthenium (Ru) nanoparticles catalysts are prepared by simple impregnation method and characterized by using different techniques such as TEM, TEM-EDX, SEM, XRD, FT-IR, surface area analysis and CO chemisorption. HYZ (different ratio of Si/Al) supported ruthenium catalysts are evaluated in hydrogenation of xylose to xylitol under green aqueous phase system. The reaction conditions are optimized by varying the stirring rate, ruthenium percent loading, xylose concentration, hydrogen partial pressure, reaction temperature and amount of catalyst to achieve the maximum conversion of xylose and selectivity to hydrogenated product xylitol. The activity of Ru/HYZ is also compared with that of conventional Ru/C catalyst at optimum reaction condition (120 C and 5.5 MPa pressure of H2 in 2 h). The reusability test of catalyst is carried out four times by recovering the catalyst from product solution.

Elucidating the effect of solid base on the hydrogenation of C5 and C6 sugars over Pt–Sn bimetallic catalyst at room temperature

Conversion of sugars into sugar alcohols at room temperature with exceedingly high yields are achieved over Pt–Sn/γ-Al2O3 catalyst in the presence of calcined hydrotalcite. pH of the reaction mixture significantly affects the conversion and selectivity for sugar alcohols. Selection of a suitable base is the key to achieve optimum yields. Various solid bases in combination with Pt–Sn/γ-Al2O3 catalysts were evaluated for hydrogenation of sugars. Amongst all combinations, the mixture (1:1 wt/wt) of Pt–Sn/γ-Al2O3 and calcined hydrotalcite showed the best results. Hydrotalcite helps to make the pH of reaction mixture alkaline at which sugar molecules undergo ring opening. The sugar molecule in open chain form has carbonyl group which can be polarized by Sn in Pt–Sn/γ-Al2O3 and Pt facilitates the hydrogenation. In the current work, effect of both; solid base and Sn as a promoter has been studied to improve the yields of sugar alcohols from various C5 and C6 sugars at very mild reaction conditions.

Unexpected reactivity related to support effects during xylose hydrogenation over ruthenium catalysts

Xylose is a major component of hemicelluloses. In this paper, its hydrogenation to xylitol in aqueous medium was investigated with two Ru/TiO2catalysts prepared with two commercial TiO2supports. A strong impact of the support on catalytic performance was evidenced. Ru/TiO2-R led to fast and selective conversion of xylose (100% conversion in 2 h at 120 °C with 99% selectivity) whereas Ru/TiO2-A gave a slower and much less selective transformation (58% conversion in 4 h at 120 °C with 17% selectivity) with the formation of several by-products. Detailed characterization of the catalysts with ICP, XRD, FTIR, TEM, H2chemisorption, N2porosimetry, TPR and acid-base titration was performed to elucidate the role of each support. TiO2-R has a small specific surface area with large ruthenium nanoparticles in weak interaction with the TiO2support and no acidity, whereas TiO2-A is a mesoporous material with a large specific surface area that is mildly acidic, and bears small ruthenium particles in strong interaction with the TiO2support. The former was very active and selective for xylose hydrogenation to xylitol whereas the latter was less active and poorly selective. Moreover, careful analysis of the reaction products also revealed that anatase TiO2can catalyze undesired side-reactions such as xylose isomerisation to various pentoses, and therefore the corresponding unexpected polyols (arabitol, ribitol) were produced during xylose conversion by hydrogenation. In a first kinetic approach, a simplified kinetic model was built to compare quantitatively intrinsic reaction rates of both catalysts. The kinetic constant for hydrogenation was 20 times higher for Ru/TiO2-R at 120 °C.

Hydrogenolysis of sorbitol into valuable C3-C2 alcohols at low H2 pressure promoted by the heterogeneous Pd/Fe3O4 catalyst

The hydrogenolysis of sorbitol and various C5-C3 polyols (xylitol; erythritol; 1,2- 1,4- and 2,3-butandiol; 1,2-propandiol; glycerol) have been investigated at low molecular hydrogen pressure (5 bar) by using Pd/Fe3O4, as heterogeneous catalyst and water as the reaction medium. Catalytic experiments show that the carbon chain of polyols is initially shortened through dehydrogenation/decarbonylation and dehydrogenation/retro-aldol mechanisms followed by a series of cascade reactions that include dehydrogenation/decarbonylation and dehydration/hydrogenation processes. At 240 °C, sorbitol is fully converted into lower alcohols with ethanol being the main reaction product in liquid phase.

Preparation method of gamma-acetyl n-propanol

The invention discloses a preparation method of gamma-acetyl n-propanol. The method includes the steps of (1) adding the hydrolysate of plant fiber or xylose and other raw materials into a reaction still, adding a two-phase reactive solvent and a catalyst, inletting hydrogen, and heating the reaction still to react for several hours; (2) carrying out standing, liquid separation and then solid-liquid separation on reaction materials in the reaction still, obtaining water phase, oil phase and the catalyst, and recycling the catalyst for reutilization; (3) concentrating water phase products, extracting 1, 4-pentanediol in the oil phase, mixing with the concentrated solution, and carrying out further separation to obtain a crude product of 1, 4-pentanediol; (4) pumping the crude product of 1, 4-pentanediol obtained from the water phase and the oil phase in step (3) to a fixed bed reactor, carrying out dehydrogenation to produce gamma-acetyl n-propanol under the action of a catalytic dehydrogenation catalyst or an oxydehydrogenation catalyst. According to the preparation method, raw materials have extensive sources, the production cost is low, no inorganic acid system is used, and the reaction process is environment-friendly.

Hormonemate Derivatives from Dothiora sp., an Endophytic Fungus

A search for cytotoxic agents from cultures of the endophytic fungus Dothiora sp., isolated from the endemic plant Launaea arborescens, led to the isolation of six new compounds structurally related to hormonemate, with moderate cytotoxic activity against different cancer cell lines. By using a bioassay-guided fractionation approach, hormonemates A-D (1-4), hormonemate (5), and hormonemates E (6) and F (7) were obtained from the acetone extract of this fungus. Their structures were determined using a combination of HRMS, ESI-qTOF-MS/MS, 1D and 2D NMR experiments, and chemical degradation. The cytotoxic activities of these compounds were evaluated by microdilution colorimetric assays against human breast adenocarcinoma (MCF-7), human liver cancer cells (HepG2), and pancreatic cancer cells (MiaPaca_2). Most of the compounds displayed cytotoxic activity against this panel.

CTAB-assisted sol-microwave method for fast synthesis of mesoporous TiO2 photocatalysts for photocatalytic conversion of glucose to value-added sugars

Fabrication technique is an important factor for development of catalysts. Titanium dioxide (TiO2) is one of efficient photocatalysts. In this work, we firstly report the fabrication of TiO2 nanoparticles by sol-microwave method with cetyltrimethylammonium bromide (CTAB) surfactant. Absence of surfactant, microwave treatment significantly reduced the cluster sizes of TiO2, but high aggregations of TiO2 particles were observed. CTAB has great impact on morphology, cluster size and mesoporous structure of TiO2. Therefore, surface area of TiO2 synthesized by sol-microwave method with 0.108 M CTAB increased from 15.97 to 37.60 m2/g. Photocatalytic activity of TiO2 was tested via the glucose conversion to produce value-added chemicals (gluconic acid, xylitol, arabinose and formic acid). It was found that surface area, mesoporous structure and pore size of TiO2 are crucial properties for glucose conversion and product distribution. From the reaction test, 0.108 M CTAB/MW-TiO2 achieved the highest glucose conversion (62.28%).