D-arabinitol

D-arabinitol Basic information
Product Name:D-arabinitol
Synonyms:D-ARA-OL;D(+)-ARABIT;D-(+)-ARABINITOL;D-ARABINITOL;ARABITOL, D-(+)-;ARABINITOL;d-[4,5-13C2]arabinitol;D-Arabitol, 99% 5GR
CAS:488-82-4
MF:C5H12O5
MW:152.15
EINECS:207-686-2
Product Categories:MonosaccharideSpecialty Synthesis;Carbohydrate Synthesis;Carbohydrates;Carbohydrates A to;Carbohydrates A-CBiochemicals and Reagents;Monosaccharides;Sugars, Carbohydrates & Glucosides;Arabinose;Biochemistry;Sugar Alcohols;Sugars;Dextrins、Sugar & Carbohydrates
Mol File:488-82-4.mol
D-arabinitol Structure
D-arabinitol Chemical Properties
Melting point 101-104 °C
alpha +10~+14゜(20℃/D)(c=5,Na2B4O7 soln.)
Boiling point 194.6°C (rough estimate)
density 1.1497 (rough estimate)
refractive index 1.3960 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility H2O: 0.1 g/mL, clear, colorless
pka13.24±0.20(Predicted)
form Fine Crystalline Powder
color White to off-white
Water Solubility Soluble in water (50 mg/ml).
Merck 14,762
BRN 1720520
LogP-3.774 (est)
CAS DataBase Reference488-82-4(CAS DataBase Reference)
EPA Substance Registry SystemD-Arabinitol (488-82-4)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 24/25-36-26
WGK Germany 3
3-10
TSCA Yes
HS Code 29054980
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
D-arabinitol Usage And Synthesis
DescriptionD-arabinitol is a characteristic metabolic product of candida species. While candida ssp. produces exclusively D-arabinitol, L-arabinitol is developed by the body’s own metabolism. D-arabinitol serum levels increase if candida yeasts proliferate within the organism and cause invasive Candidiasis. Both D-arabinitol and L-arabinitol are present in normal urine, and can easily be measured by gas chromatography of urine samples collected on filter paper.
Chemical Propertieswhite to off-white fine crystalline powder
OccurrenceD-Arabinitol (lyxitol) is found in lichens; in a variety of fungi; in the urediospores of wheat stem rust; in the dried herbiage of the Peruvian shrub, pichi, along with D-mannitol, dulcitol, and perseitol; and in the avocado. It is formed by fermentation of glucose and in 40% yields using blackstrap molasses. D-Arabinitol is 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.
UsesD-Arabitol, a rare sugar alcohol, is a substrate used to identify, differentiate and characterize enzyme such as the gluconobacter oxydans dehydrogenase(s), Gox2181, hyperthermophilic D-arabitol dehydrogenase from Thermotoga maritime and NAD-dependent D-arabitoldehydrogenase from acetic acid bacterium, Acetobacter suboxydans.
DefinitionChEBI: D-arabinitol is the D-enantiomer of arabinitol. It is an enantiomer of a L-arabinitol. It is a metabolite found in the aging mouse brain.
Biotechnological ApplicationsD-arabinitol detection
Another approach to the diagnosis of invasive candidosis involves the detection in serum or urine of a metabolite, D-arabinitol, which is produced by most of the medically important Candida species with the exception of C. krusei and perhaps C. glabrata. Various methods have been developed to measure D-arabinitol concentrations in human serum and urine, including enzymatic-fluorometric and enzymatic-colorimetric procedures. Because increased levels of arabinitol are also found in human body fluids when renal function is impaired, the results are reported as the D-arabinitol- creatinine ratio. Although several large studies have demonstrated that patients with candidaemia have ele- vated serum D-arabinitol- creatinine ratios, this approach has still to achieve widespread clinical use.
Purification MethodsThis 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.]
D-arabinitol Preparation Products And Raw materials
Preparation ProductsMANNOSE
5-Bromo-4-chloro-3-indolyl-beta-D-galactoside DIACETONE-D-GLUCOSE Gluconic acid D-arabinitol 1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol MUCIC ACID Span 60 Span 20 HEXA(2-CYANOETHOXY) CYCLOHEXANE D-GLUCOHEPTONO-1,4-LACTONE EPI-INOSITOL Inositol nicotinate D-GLUCOSE DIETHYL MERCAPTAL adipiodone, dimeglumine salt Sorbitol D-SACCHARIC ACID 1,4-LACTONE 2,5-O-METHYLENE-D-MANNITOL α-Chloralose

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