87-72-9

Basic information

• Product Name: Pentose
• Synonyms: ARABITOL, L-(-)-(RG);L-Arabinopyranose;L-ARABINOSE extrapure;(2R,3R,4S,5S)-oxane-2,3,4,5-tetrol;L-Arabinose 98%;L-(+)-Arabinose, L-arabinose;l-[1-13C]arabinose;l-[2-13C]arabinose
• CAS NO: 87-72-9
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• EINECS: 226-214-6
• Product Categories: Sugars, Carbohydrates & Glucosides;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives;carbohydrate;Food Additives;Inhibitors
• Mol File: 87-72-9.mol

Chemical Properties

• Melting Point: 160-163 °C(lit.)
• Boiling Point: 191.65°C (rough estimate)
• Flash Point: 155.3 °C
• Appearance: White/Fine Crystalline Powder
• Density: 1.1897 (rough estimate)
• Refractive Index: 1.3920 (estimate)
• Storage Temp.: Store at RT.
• PKA: 12.26±0.70(Predicted)
• Water Solubility: soluble
• Merck: 14,761
• BRN: 1723085
• CAS DataBase Reference: Pentose(CAS DataBase Reference)
• NIST Chemistry Reference: Pentose(87-72-9)
• EPA Substance Registry System: Pentose(87-72-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 87-72-9(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
L(+)-Arabinose is used as a biochemical research tool for identifying, differentiating, and characterizing pentose sugar isomerase, an enzyme that catalyzes the interconversion of pentose sugars.
Used in Microbial Culture:
L(+)-Arabinose serves as a carbon source in microbial culture, providing an essential nutrient for the growth and metabolism of certain microorganisms.
Used in Bioproduction:
L(+)-Arabinose is involved in the bioproduction of L-ribose, an important sugar molecule that plays a crucial role in various biological processes, including the synthesis of nucleic acids and energy metabolism.
Used in Flavor Production:
L(+)-Arabinose finds application in the production of savory reaction flavors, which are used to enhance the taste and aroma of various food products.
Used in Antiviral Drug Development:
The derivatives of L(+)-Arabinose are used in the development of antiviral agents, such as nucleoside analogs, which can inhibit viral replication and treat viral infections.
Used in Plant Biopolymer Composition:
As a base component of hemicellulose and pectin, L(+)-Arabinose plays a critical role in the structure and function of plant cell walls, contributing to their mechanical strength and defense against pathogens.

Purification Methods

beta-L-(+)-Arabinose is recrystallised slowly, twice, from 80% aqueous EtOH, then dried under vacuum over P2O5. It can also be purified by heating the arabinose (200g) with glacial acetic acid (300mL) on a boiling water bath for 45minutes, cooling, filtering, washing with 95% EtOH (500mL) in four portions and drying at 56-60o over P2O5. It has been recrystallised from 5times its weight of 76% EtOH using charcoal (10g) to yield 127g, m 155-157o, [] 20D +190.6o and mutarotating to +104o (c 4, H2O). [Anderson & Sands Org Synth Coll Vol I 67 1941, Wolfrom & Christian J Am Chem Soc 48 3172 1926, Beilstein 1 IV 4217.]

InChI:InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 107091-09-8 3-O-β-D-galactopyranosyl-(1->2)-<β-D-xylopyranosyl-(1->3)>-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-apiofuranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-<β-D-glucopyranosyl-(1->3)>-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside. 
• 67-56-1 methanol 
• 552-71-6 D-(+)-xylobiose 
• 87-72-9 D-Xylose 
• 6294-16-2 D-galacturonic acid 
• 22416-59-7 xylotriose 
• 58-86-6 D-xylose 
• 95272-12-1 O-α-D-xylopyranosyl-(1->6)-D-glucopyranose 
• 91-09-8 methyl xyloside 
• 87-99-0 XYLITOL 
• 532-20-7 D-lyxose 
• 141923-44-6 α-L-arabinofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-D-xylopyranose 
• 108-24-7 acetic anhydride 

Downstream Products

• 91-09-8 methyl xyloside 
• 612-05-5 methyl-β-D-xylopyranoside 
• 91-09-8 methyl-α-D-xylopyranoside 
• 85051-64-5 (2R,3R,4S)-5-[(4,5-Diphenyl-oxazol-2-yl)-hydrazono]-pentane-1,2,3,4-tetraol 
• 62410-08-6 5-deoxy-1,2-O-isopropylidene-α-D-xylohexofuranose 
• 76222-63-4 3,5-O-isopropylidene-D-xylofuranose 
• 13039-94-6 2,3,4,5-di-O-isopropylidene-D-xylose aldehyde 
• 2001-96-9 p-nitrophenyl β-D-xylopyranoside 
• 25217-96-3 p-Acetyl-phenyl-β-D-xylopyranosid 
• 161879-31-8 1-(3-methoxy-4-β-D-xylopyranosyloxy-phenyl)-ethanone 
• 98-01-1 furfural 
• 141-46-8 Glycolaldehyde 
• 116-09-6 hydroxy-2-propanone 
• 532-20-7 D-lyxose 

Relevant articles and documents

New triterpenoid saponin from the stems of Albizia adianthifolia (Schumach.) W.Wight

As part of our continuing study of apoptosis-inducing saponins from Cameroonian Albizia genus, one new triterpenoid saponin, named adianthifolioside J (1), together with the known gummiferaoside E (2), were isolated from Albizia adianthifolia stems. The s

New flavonoid glycosides from Xanthium strumarium with their protein tyrosine phosphatase 1B inhibitory activity

Two new flavonoid glycosides named 6-hydroxy-3-methoxy-apigenin 7-O-α-?-rhamnopyranoside (1) and 3-hydroxyl-apigenin 8-C-β-?-xylopyranoside (2), along with five known compounds (3-7), were isolated from Xanthium strumarium. Their structures were elucidate

Ursane-type triterpene oligoglycosides with anti-hepatosteatosis and anti-hyperlipidemic activity from the leaves of Ilex paraguariensis A. St.-Hil.

The methanol extract from the leaves of Ilex paraguariensis A. St.-Hil. (Aquifoliaceae), popularly known as mate, maté, or yerba maté, inhibits the intracellular triglyceride accumulation in HepG2 cells and suppresses the plasma triglyceride elevation in olive oil-treated mice. Three new triterpene saponins, termed mateosides I (1), II (2), and III (3), were isolated from the extract along with 29 known compounds. The structures of 1–3 were elucidated based on chemical and spectroscopic evidence. Among the isolates, principal saponin constituents, 2 and matesaponins 1 (7) and 2 (9), potently inhibited the triglyceride accumulation in HepG2 cells simultaneously treated with oleic acid and high glucose. In vivo assay of the methanol extract of I. paraguariensis revealed that 7 and 9 showed anti-hyperlipidemic activities in olive oil-treated mice. These results suggested that the saponin constituents of I. paraguariensis could be valuable bioactive marker for the anti-obesogenic activity. Graphical abstract: [Figure not available: see fulltext.]

A new triterpenoid saponin from Glinus oppositifolius

From the ethanol extract of Glinus oppositifolius, collected at Phu Yen province, Viet Nam, one new triterpenoid saponin (1) and four known compounds (2–5) were isolated. By means of NMR and HR-ESI-MS analyses, their structure was elucidated as 3-O-(β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl)spergulagenin A or glinusopposide V (1), glinusopposide L (2), spergulin B (3), vitexin (4) and astralagin (5). Two compounds (1–2) showed weak inhibitory activity against α-glucosidase.

Protective effects of four new saponins from Gynostemma pentaphyllum against hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells

Gynostemma pentaphyllum has been used as a medicine-food homologious health product in China for a long time. This research aimed to isolate and identify its active compounds with protective effects against hydrogen peroxide induced SH-SY5Y cell death. Four new dammarane-type saponins were isolated from G. pentaphyllum using various chromatographic methods. They were identified as gypenoside S1 (1), gypenoside S3 (2), gypenoside S2 (3) and gypenoside S4 (4), respectively by HRESIMS and NMR spectra. Their cytotoxic activity was evaluated against three human cancer cell lines, A549 (lung), HepG2 (liver), SH-SY5Y (nerve), by MTT method. They showed low cytotoxicities with the IC50 values of more than 100 μM on three cancer cell lines. However, they appeared protective effects against hydrogen peroxide induced SH-SY5Y cell death in a dose-dependent manner. They recovered cell viability more than 69% at the concentration of 20 μM from 66%, while as vitamin C to 67%. Compound 3 and 4 recovered more than 79% at 100 μM. The present study suggests that G. pentaphyllum has antioxidative potential and the saponins from G. pentaphyllum are considered as the active compounds with safe and neuroprotecitve effect.

Transformation of aldehydes into nitriles in an aqueous medium using O-phenylhydroxylamine as the nitrogen source

The conversion of an aldehyde into a nitrile can be efficiently performed using O-phenylhydroxylamine hydrochloride in buffered aqueous solutions. The reported method is specifically optimized for aqueous-soluble substrates including carbohydrates. Several reducing sugars including monosaccharides, disaccharides, and silyl-protected saccharides were transformed into cyanohydrins in high yields. The reaction conditions are also suitable for the formation of nitriles from various types of hydrophobic aldehyde substrates. Furthermore, cyanide can be eliminated from cyanohydrins, analogous to the Wohl degradation, by utilizing a readily-removed weakly basic resin as a promoter.

Oleanane-type saponins and prosapogenins from Albizia julibrissin and their cytotoxic activities

Two undescribed oleanane-type saponins, julibrosides K–L, along with three undescribed oleanane-type prosapogenins, julibrosides M–O, were isolated from the stem bark of Albizia julibrissin Durazz. and the mild alkaline hydrolysate of the total saponin, r

Isolation and structural characterization of four diastereomeric lignan glycosides from Abies holophylla and their neuroprotective activity

Diastereomers are a type of a stereoisomer and they are often isolated as a mixture due to their similar physical properties. Through HPLC technique, we isolated four stereoisomeric lignan glycosides, holophyllosides A–D (1–4), from the trunk of Abies holophylla Maxim. which were first isolated as a mixture 25 years ago. The planar structures of 1–4 were characterized by conventional 1D and 2D NMR data analysis and their stereochemistry was determined via empirical comparison of their 13C NMR chemical shifts and 3JH-H coupling constants with the reported values, enzymatic hydrolysis followed by LC-MS analysis, and ECD experiment. Of the four stereoisomers isolated, only compounds 1, 3, and 4 showed moderate neuroprotective activity by inducing NGF secretion in C6 cells whereas 2 did not. This study highlights again the stereochemical importance of molecules in their biological and pharmaceutical application.

Arenarosides A-G, Polyhydroxylated Oleanane-Type Saponins from Polycarpaea arenaria and their Cytotoxic and Antiangiogenic Activities

Seven new polyhydroxylated oleanane-type triterpene saponins, arenarosides A-G (1-7), together with four known compounds, were isolated from an ethanol extract of the aerial parts of the Vietnamese plant Polycarpaea arenaria. The chemical structures of the newly isolated oleanane saponins were elucidated on the basis of spectroscopic and spectrometric analysis, especially 2D NMR and HRMS. Biological evaluation revealed that 3, 4, 6, and 7 showed moderate activities against four human cancer cell lines (A549, HTC116, PC3, and RT112) with IC50 values of 6.0-9.9 μM, and 3, 4, 5, and 7 also displayed promising antiangiogenesis effects with IC50 values 5 μM in the test system used. Among the isolates, arenaroside D (4) exhibited the most potent inhibitory effects, not only in cancer cell proliferation but also in angiogenic activities. Preliminary SAR studies revealed that the presence of an acetyl group at C-22 in oleanane-type triterpene saponins increases these bioactivities.

Polythosides A and B, two new triterpenoid saponins from the roots of Acacia polyacantha Willd. (Mimosaceae)

Two new oleanane-type triterpene saponins, named polythosides A and B (1 and 2), together with a known compound, silphioside E (3), were isolated from the roots of Acacia polyacantha. Their structures were elucidated by analysis of 1D and 2D-NMR experiments, and mass spectrometry (HR-ESITOF-MS) as oleanolic acid 3-O-β-D-galactopyranosyl-(1→2)-β-D-xylopyranosyl-(1→6)-[β-D-xylopyranosyl-(1→4)]-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranoside (1), 3-O-[β-D-galactopyranosyl-(1→2)-β-D-xylopyranosyl-(1→6)-[β-D-xylopyranosyl-(1→4)]-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranosyl] oleanolic acid-28-O-β-D-glucopyranosyl ester (2) and 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (3). The cytotoxic effect of isolated saponins was evaluated on the H4IIE rat hepatoma cell line. The results show that none of the compounds (assayed at 100 μM) showed cytotoxicity against H4IIE cells.