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Xylose(CAS No. 25990-60-7)

Xylose C5H10O5 (cas 25990-60-7) Molecular Structure

25990-60-7 Structure

Identification and Related Records

【Name】
Xylose
【CAS Registry number】
25990-60-7
【Synonyms】
DL-Xylose
(?à)-Xylose
dl-Xylose
【EINECS(EC#)】
247-395-8
【Molecular Formula】
C5H10 O5 (Products with the same molecular formula)
【Molecular Weight】
150.13
【Inchi】
InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5+/m1/s1
【InChIKey】
SRBFZHDQGSBBOR-LECHCGJUSA-N
【Canonical SMILES】
C1C(C(C(C(O1)O)O)O)O
【Isomers smiles】
C1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O
【MOL File】
25990-60-7.mol

Chemical and Physical Properties

【Density】
1.757g/cm3
【Melting Point】
133-136 °C
【Boiling Point】
333.2°Cat760mmHg
【Flash Point】
155.3°C
【Solubilities】
1 g dissolves in 0.8 ml water; sol in pyridine & hot alc
【Color/Form】
Monoclinic needles or prisms
White crystalline powder
【Spectral properties】
SADTLER REFERENCE NUMBER: 1068 (IR, PRISM)
Specific optical rotation: +92 deg & +18.6 deg (16 hr, 10%) @ 20 deg C/D
IR: 15302 (Sadtler Research Laboratories IR Grating Collection)
UV: 6-55 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 7074 (Sadtler Research Laboratories Spectral Collection)
【Computed Properties】
Molecular Weight:150.1299 [g/mol]
Molecular Formula:C5H10O5
XLogP3-AA:-2.5
H-Bond Donor:4
H-Bond Acceptor:5
Rotatable Bond Count:0
Exact Mass:150.052823
MonoIsotopic Mass:150.052823
Topological Polar Surface Area:90.2
Heavy Atom Count:10
Formal Charge:0
Complexity:117
Isotope Atom Count:0
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:4
Feature 3D Ring Count:1
Effective Rotor Count:1.2
Conformer Sampling RMSD:0.4
CID Conformer Count:4

Safety and Handling

【Safety Statements 】
S24/25
【Formulations/Preparations】
Grades: Reagent, Technical
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Isolation from corn cobs by boiling with 8% sulfuric acid. Peanut shells & cottonseed hulls also are practical sources of xylose.

Biomedical Effects and Toxicity

【Therapeutic Uses】
XYLOSE BLOOD LEVEL MEASUREMENTS...TO DETERMINE WHETHER ABNORMALLY LOW URINARY XYLOSE EXCRETION IS DUE TO IMPAIRED ABSORPTION OR RENAL INSUFFICIENCY. BLOOD XYLOSE LEVELS /DETERMINED/ 2 HR AFTER INGESTION OF 25 G DOSE.
/DIFFERENTIATE/ STEATORRHEA CAUSED BY PANCREATIC INSUFFICIENCY FROM THAT CAUSED BY MALABSORPTION /5 G DISSOLVED IN 150 ML WATER OR 25 G DISSOLVED IN 250 ML WATER, FOLLOWED BY 250 ML WATER, ORAL. URINE POOLED DURING NEXT 5 HR & QUANTITY OF XYLOSE DETERMINED/.
EVALUATE INTESTINAL ABSORPTION...DIAGNOSIS OF MALABSORPTIVE STATES DUE TO DISEASES INVOLVING INTESTINAL MUCOSA /5 G DISSOLVED IN 150 ML WATER OR 25 G DISSOLVED IN 250 ML WATER, FOLLOWED BY 250 ML WATER, ORAL. URINE POOLED DURING NEXT 5 HR & QUANTITY OF XYLOSE DETERMINED/.
DIAGNOSIS OF MALABSORPTIVE STATES DUE TO...SURGICAL RESECTION. /ASSESS/ DEG OF IMPAIRED ABSORPTION OR EXTENT OF RESPONSE TO THERAPY /5 G DISSOLVED IN 250 ML WATER & ADMIN ORALLY. ADDITIONAL FLUIDS PERMITTED. URINE COLLECTED IN 2 CONSECUTIVE PERIODS OF 2 & 3 HR. XYLOSE CONTENT DETERMINED/.
FOR INFANTS, YOUNG CHILDREN OR ELDERLY INCONTINENT PATIENTS...XYLOSE BLOOD LEVELS MAY BE USED TO EVALUATE INTESTINAL ABSORPTION /500 MG/KG BODY WT (OR MAX OF 25 G) AS 5-10% AQ SOLN, ORAL. XYLOSE LEVELS ARE DETERMINED IN BLOOD SAMPLES TAKEN 30 MIN, 1 HR, & 2 HR AFTER XYLOSE ADMIN/.
【Biomedical Effects and Toxicity】
XYLOSE HAS BEEN SHOWN TO GET INTO AQ HUMOR /OF RATS/ FROM GENERAL CIRCULATION & THEREFORE TO HAVE ACCESS TO LENS.
/ABSORBED/ FROM GI TRACT...5-G DOSES...ABSORBED MORE RAPIDLY & COMPLETELY THAN ARE 25-G DOSES...AT LEAST 60%...ABSORBED IN PROXIMAL PART OF SMALL INTESTINE... NOT DEPENDENT UPON PRESENCE OF BILE OR PANCREATIC JUICE.../PEAK BLOOD LEVELS/ 1 TO 2 HR...TO 0 AFTER...5 HR /HUMAN, ORAL 5 OR 25 G/.
PLASMA HALF-LIFE...ABOUT 1 HR /IV ADMIN/...ABOUT 60%...METABOLIZED TO CARBON DIOXIDE & WATER, D-THREITOL, &...UNIDENTIFIED METABOLITES...EXCRETED IN URINE...ABOUT 25% OF 25 G /DOSE/ & ABOUT 35% OF 5 G /DOSE/ EXCRETED UNCHANGED IN URINE WITHIN 5 HR /HUMAN, ORAL/.
URINARY EXCRETION /MAINLY BY/ GLOMERULAR FILTRATION...SOME TUBULAR RESORPTION MAY OCCUR /HUMAN, ORAL/.
SALMONELLA TYPHIMURIUM LT2 GROWS ON D-XYLOSE AS SOLE CARBON SOURCE WITH GENERATION TIME OF 105 TO 110 MIN. APPARENT KM FOR D-XYLOSE UPTAKE WAS 0.41 MM.
D-XYLITOL & L-ARABINOSE COMPETED AGAINST C-XYLOSE UPTAKE. OSMOTIC SHOCK REDUCED UPTAKE OF D-XYLOSE BY ABOUT 50%.
The pharmacokinetics of xylose (D xylose; I) after an oral doze of 2S g and intravenous injection of 10 g dose were studied in 10 patients (aged 37 79 yr) with impaired renal function, 3 of whom were being evaluated for intestinal malabsorption. The 0.32 1/kg mean distribution volume of I in patients with uncomplicated renal impairment was larger than the value of 0.21 1/kg That was previously reported for normal subjects. Renal clearance was also reduced, averaging 87% of glomerular filtration rate estimated from creatinine clearance, so that the mean elimination phase half life was prolonged to 138 min from 75 min in normal individuals. The 2S g oral I Jose was 77.4% absorbed in the patients with uncomplicated renal impairment, similar to the 69.4% absorption reported in normal subjects. However, The absorption half life was prolonged from 31 min in normal subjects to 62 min. The serum concentration measured one h after The oral dose was best correlated with the extent of I absorption and the standard lower normal limit of 0.2 mg/ml was satisfactory. [Worwag EM et al; Clin Pharmacol Ther 41 (Mar): 351 7 (1987)] PubMed Abstract
1. The transplacental transfer of D-xylose was investigated in the present study. 2. Umbilical perfusion of the rat term placenta was used to study materno-foetal (M-F) and foetomaternal (F-M) transfer of this compound. 3. D-Xylose was found to cross the rat term placenta very quickly in the M-F direction, with subsequent accumulation in the foetal compartment (the F-M ratio being 2.23 at the end of the experiments). In contrast, no transfer in the F-M direction was observed. 4. A possible facilitation of the transplacental transfer of D-xylose from the mother to foetus in rats is suggested. [Staud F et al; Clin Exp Pharmacol Physiol 25 (1): 54-6 (1998)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from an estimated log Kow of -1.98(2,SRC) and a regression-derived equation(3), indicates that D-xylose is expected to have very high mobility in soil(SRC). Volatilization of D-xylose from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). D-Xylose is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.4X10-7 mm Hg(SRC), determined from a fragment constant method(5). D-Xylose is a simple monosaccharide and should be readily biodegradable in the environment(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from an estimated log Kow of -1.98(2,SRC) and a regression-derived equation(3), indicates that D-xylose is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). D-Xylose was biodegraded 63 percent in a 15-day river die away test(6).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), D-xylose, which has an estimated vapor pressure of 9.6X10-7 mm Hg at 25 deg C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase D-xylose is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 hours(SRC) from its estimated rate constant of 7.4X10-11 cu cm/molecule-sec at 25 deg C(SRC), determined from a fragment constant estimation method(3). Particulate-phase D-xylose may be removed from the air by wet and dry deposition(SRC).

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