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Literature & References

dextro-xylose

General Material Information

Preferred name	dextro-xylose
Trivial Name	(+)-Xylose
Short Description	D-xylose
Formula	C5 H10 O5
CAS Number	58-86-6
Deleted CAS Number	133-56-2
FEMA Number	3606
ECHA Number	200-400-7
FDA UNII	C791ZE5K1W
Nikkaji Number	J8.437I
Beilstein Number	1562108
MDL	MFCD00151475
COE Number	11902
xLogP3-AA	-2.50 (est)
NMR Predictor	External link
FDA Patent	No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm	58-86-6 ; D-XYLOSE
Synonyms	(2S,3R,4S,5R)- oxane-2,3,4,5-tetrol (2S,3R,4S,5R)-2,3,4,5-tetrahydroxypentanal wood sugar xylo-pfan xylomed xylopyranose a- xylopyranose a-D- xylopyranose (+)- xylose a-D- xylose D- xylose D-(+)- xylose D- xylose USP xylose, D- D- xylose, natural XYP XYS (2S,3R,4S,5R)-oxane-2,3,4,5-tetrol D-Xylose Xylose (+)-Xylose D-(+)-Xylose (2R,3S,4R)-2,3,4,5-Tetrahydroxypentanal

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Literature & References

	(2S,3R,4S,5R)-oxane-2,3,4,5-tetrol
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	58-86-6
Pubchem (cid):	6027
Pubchem (sid):	134971957
Pherobase:	View

Publications by PubMed
Identification of Bitter Modulating Maillard-Catechin Reaction Products.
A New α-Galactosidase from Thermoacidophilic Alicyclobacillus sp. A4 with Wide Acceptor Specificity for Transglycosylation.
Overcoming inefficient cellobiose fermentation by cellobiose phosphorylase in the presence of xylose.
The effect of thyme and tea tree oils on morphology and metabolism of Candida albicans.
L-Arabinose isomerase and D-xylose isomerase from Lactobacillus reuteri: characterization, coexpression in the food grade host Lactobacillus plantarum, and application in the conversion of D-galactose and D-glucose.
Characterization of plant-derived lactococci on the basis of their volatile compounds profile when grown in milk.
[Method of quantitative analysis by HPLC and confirmation by LC-MS of sugar alcohols in foods].
Ammoxidation of lignocellulosic materials: formation of nonheterocyclic nitrogenous compounds from monosaccharides.
Characterization and bioactivity of polysaccharides obtained from pine cones of Pinus koraiensis by graded ethanol precipitation.
Disruption of the L-arabitol dehydrogenase encoding gene in Aspergillus tubingensis results in increased xylanase production.
Oral serum-derived bovine immunoglobulin improves duodenal immune reconstitution and absorption function in patients with HIV enteropathy.
In vitro growth of four individual human gut bacteria on oligosaccharides produced by chemoenzymatic synthesis.
Subcutaneous application of levothyroxine as successful treatment option in a patient with malabsorption.
Low pH D-xylonate production with Pichia kudriavzevii.
Intestinal absorption and pancreatic function are preserved in anorexia nervosa patients in both a severely malnourished state and after recovery.
Microbial D-xylonate production.
Coconut-derived D-xylose affects postprandial glucose and insulin responses in healthy individuals.
Red pigment production by Penicillium purpurogenum GH2 is influenced by pH and temperature.
Characterization of Candida sp. NY7122, a novel pentose-fermenting soil yeast.
Discovery of nigerose phosphorylase from Clostridium phytofermentans.
Contribution of sulfur-containing compounds to the colour-inhibiting effect and improved antioxidant activity of Maillard reaction products of soybean protein hydrolysates.
Microbial and bioconversion production of D-xylitol and its detection and application.
The genetics, transcriptional profiles, and catalytic properties of UDP-alpha-D-xylose 4-epimerases from barley.
[Study on the structure and constituents of polysaccharide from ganoderma lucidum].
Quantification of xylitol in foods by an indirect competitive immunoassay.
Physicochemical properties and antioxidant capacity of 3 polysaccharides from green tea, oolong tea, and black tea.
In vitro fermentation of arabinoxylan-derived carbohydrates by bifidobacteria and mixed fecal microbiota.
Xylose reductase activity in Debaryomyces hansenii UFV-170 cultivated in semi-synthetic medium and cotton husk hemicellulose hydrolyzate.
Acetobacter fabarum sp. nov., an acetic acid bacterium from a Ghanaian cocoa bean heap fermentation.
Effect of intestinal pacing on small bowel transit and nutrient absorption in healthy volunteers.
Characterization of pyranose dehydrogenase from Agaricus meleagris and its application in the C-2 specific conversion of D-galactose.
In vivo anti-influenza virus activity of an immunomodulatory acidic polysaccharide isolated from Cordyceps militaris grown on germinated soybeans.
Reductively aminated D-xylose-albumin conjugate as the immunogen for generation of IgG and IgE antibodies specific to D-xylitol, a haptenic allergen.
Release of D-xylose from wheat straw by acid and xylanase hydrolysis and purification of xylitol.
Characterization of weight loss and weight regain mechanisms after Roux-en-Y gastric bypass in rats.
Description of a new species, Bifidobacterium crudilactis sp. nov., isolated from raw milk and raw milk cheeses.
Properties of pyranose dehydrogenase purified from the litter-degrading fungus Agaricus xanthoderma.
Chemistry and some biological effects of model melanoidins and pigments as Maillard intermediates.
[Isolation and identification of a bacterial strain JS018 capable of degrading several kinds of organophosphate pesticides].
Hypothalamic integration of immune function and metabolism.
Discovery of natural atypical nonhemolytic Listeria seeligeri isolates.
Determination of acephate in human urine.
Reaction on D-glucal by an inverting phosphorylase to synthesize derivatives of 2-deoxy-beta-D-arabino-hexopyranosyl-(1-->4)-D-glucose (2II-deoxycellobiose).
Treatment of short gut syndrome with early living related small bowel transplantation.
Direct production of D-arabinose from D-xylose by a coupling reaction using D-xylose isomerase, D-tagatose 3-epimerase and D-arabinose isomerase.
Effect of pretreatment of food gluten with prolyl endopeptidase on gluten-induced malabsorption in celiac sprue.
Neutron diffraction and computer simulation studies of D-xylose.
Xylanase production by fungal strains on spent sulphite liquor.
Lack of carcinogenicity of D-xylose given in the diet to F344 rats for two years.
[Recent advances in structures and relative enzyme properties of xylanase].
Isomerisation of aldoses in pyridine in the presence of aluminium oxide.
Mode of action of xylogalacturonan hydrolase towards xylogalacturonan and xylogalacturonan oligosaccharides.
Saccharomyces cerevisiae engineered for xylose metabolism exhibits a respiratory response.
Novel reactions of L-rhamnose isomerase from Pseudomonas stutzeri and its relation with D-xylose isomerase via substrate specificity.
Nonenzymatic browning kinetics of a carbohydrate-based low-moisture food system at temperatures applicable to spray drying.
4-hydroxy-2,5-dimethyl-3(2H)-furanone formation by Zygosaccharomyces rouxii: effect of the medium.
Multiple forms of xylose reductase in Candida intermedia: comparison of their functional properties using quantitative structure-activity relationships, steady-state kinetic analysis, and pH studies.
Biogenetic studies in Syringa vulgaris L.: bioconversion of (18)O(2H)-labeled precursors into lilac aldehydes and lilac alcohols.
Analysis of reducing carbohydrates by reductive tryptamine derivatization prior to micellar electrokinetic capillary chromatography.
Enteral feeding of premature infants with Saccharomyces boulardii.
Pathogenicity of turkey coronavirus in turkeys and chickens.
Enzymatic synthesis of a library of beta-(1-->4) hetero- D-glucose and D-xylose-based oligosaccharides employing cellodextrin phosphorylase.
Staphylococcus equorum subsp. linens, subsp. nov., a starter culture component for surface ripened semi-hard cheeses.
Nutritional evaluation and functional properties of quinoa (Chenopodium quinoa) flour.
Characterization of a cellobiose phosphorylase from a hyperthermophilic eubacterium, Thermotoga maritima MSB8.
Effect of molecular structure on the conductivity of amorphous carbohydrate-water-KCl mixtures in the supercooled liquid state.
Low-dose growth hormone in adult home parenteral nutrition-dependent short bowel syndrome patients: a positive study.
Biogenetic studies in Syringa vulgaris L.: synthesis and bioconversion of deuterium-labeled precursors into lilac aldehydes and lilac alcohols.
Optimal growth and ethanol production from xylose by recombinant Saccharomyces cerevisiae require moderate D-xylulokinase activity.
Screening of facultative anaerobic bacteria utilizing D-xylose for xylitol production.
Carnobacterium viridans sp. nov., an alkaliphilic, facultative anaerobe isolated from refrigerated, vacuum-packed bologna sausage.
Performance testing of Zymomonas mobilis metabolically engineered for cofermentation of glucose, xylose, and arabinose.
Weissella kimchii sp. nov., a novel lactic acid bacterium from kimchi.
Application of Saccharomyces cerevisiae and Pichia stipitis karyoductants to the production of ethanol from xylose.
Xylose as a nectar sugar: from biochemistry to ecology.
New efficient amylase-producing strains of Lactobacillus plantarum and L. fermentum isolated from different Nigerian traditional fermented foods.
Transient-state and steady-state kinetic studies of the mechanism of NADH-dependent aldehyde reduction catalyzed by xylose reductase from the yeast Candida tenuis.
Purification and characterization of pyranose oxidase from the white rot fungus Trametes multicolor.
Exploring the active site of yeast xylose reductase by site-directed mutagenesis of sequence motifs characteristic of two dehydrogenase/reductase family types.
Structural and functional properties of aldose xylose reductase from the D-xylose-metabolizing yeast Candida tenuis.
Use of an orally administered combined sugar solution to evaluate intestinal absorption and permeability in cats.
Conversion of sugars to 1,2-propanediol by Thermoanaerobacterium thermosaccharolyticum HG-8.
Haloanaerobium fermentans sp. nov., a strictly anaerobic, fermentative halophile isolated from fermented puffer fish ovaries.
[A 13-week subchronic toxicity study of D-xylose in F344 rats].
Effect of casein-derived peptides on D-xylose absorption assessed by H2 breath test in normal volunteers.
D-Xylose metabolism by Candida intermedia: isolation and characterisation of two forms of aldose reductase with different coenzyme specificities.
Food-induced malabsorption syndromes.
Variation in the degree of D-xylose substitution in water-extractable European durum wheat (Triticum durum desf.) semolina arabinoxylans.
Distribution and structural variation of arabinoxylans in common wheat mill streams.
Binding energy and specificity in the catalytic mechanism of yeast aldose reductases.
Increased intestinal glucose absorption and postprandial hyperglycaemia at the early step of glucose intolerance in Otsuka Long-Evans Tokushima Fatty rats.
GLP-2 augments the adaptive response to massive intestinal resection in rat.
Lowering the pH optimum of D-xylose isomerase: the effect of mutations of the negatively charged residues.
[Effect of casein derived peptides on D-xylose absorption and small intestinal motility in dogs].
Effects of glucagon on postprandial carbohydrate metabolism in nondiabetic humans.
Physiologic response to a protein, carbohydrate, fat meal in patients with human immunodeficiency virus who underwent small intestinal enteropathy as characterized by a kinetic model of D-xylose absorption.
NAD(P)H-dependent aldose reductase from the xylose-assimilating yeast Candida tenuis. Isolation, characterization and biochemical properties of the enzyme.
Effect of growth hormone, glutamine, and diet on adaptation in short-bowel syndrome: a randomized, controlled study.
Production of Xylitol from D-xylose by Debaryomyces hansenii.
Hypolactasia and metabolic changes in post-menopausal women.
Purification and Characterization of a [beta]-D-Xylosidase and an Endo-Xylanase from Wheat Flour.
Continuous enzymatic production of xylitol with simultaneous coenzyme regeneration in a charged membrane reactor.
Kinetics of mRNA and protein synthesis of genes controlled by the 1,4-beta-endoxylanase A promoter in controlled fermentations of Aspergillus awamori.
An expression system based on the promoter region of the Aspergillus awamori 1,4-beta-endoxylanase A gene.
Molecular and industrial aspects of glucose isomerase.
Effect of casein and casein hydrolysate on small bowel motility and D-xylose absorption in dogs.
Probing the roles of active site residues in D-xylose isomerase.
[Effect of casein on D-xylose absorption assessed by H2 breath test].
Perturbing the metal site in D-xylose isomerase. Effect of mutations of His-220 on enzyme stability.
The effect of cell density on the production of xylitol from D-xylose by yeast.
Kinetic analysis of D-xylose absorption after its intragastric administration to mares deprived of food.
[Apple powder in the treatment of patients with chronic enteritis].
Experimental infection of specific-pathogen-free turkey poults with single and combined enterovirus and group A rotavirus.
Kinetic analysis of D-xylose distribution after intravenous administration to mares.
Fluorescent properties of the Escherichia coli D-xylose isomerase active site.
Nutritional value of D-xylose and L-arabinose for broiler chicks.
Nutritional status and food intake in human immunodeficiency virus infection. GI/HIV Study Group.
Complementation of the inability of Lactobacillus strains to utilize D-xylose with D-xylose catabolism-encoding genes of Lactobacillus pentosus.
The effect of exercise associated with acute poisoning with potassium nitrate and sodium nitrite on the processes of intestinal absorption of D-xylose in rats.
The effect of exercise associated with subchronic poisoning with potassium nitrate and sodium nitrite on the processes of intestinal absorption of D-xylose in rats.
The effect of acute poisoning with potassium nitrate and sodium nitrite on the processes of intestinal absorption of D-xylose in rats.
The effect of subchronic poisoning with potassium nitrate and sodium nitrite on the processes of intestinal absorption of D-xylose in rats.
[The absorption function of the small intestine and the effect on it of diet therapy in food allergy in children].
Impaired intestinal function in symptomatic HIV infection.
Cellulase production by Trichoderma reesei when cultured on xylose-based media supplemented with sorbose.
Cloning and expression of the Clostridium thermosulfurogenes glucose isomerase gene in Escherichia coli and Bacillus subtilis.
[Isolation of Listeria ivanovii in Slovakia].
[The characteristics of absorption in the small intestine of young infants with hypotrophy and encephalopathy undergoing protein-anabolic therapy].
The solubilization of a glucuronyltransferase involved in pea (Pisum sativum var. Alaska) glucuronoxylan synthesis.
Effect of food deprivation on D-xylose absorption test results in mares.
Exocrine pancreatic function in patients with progressive systemic sclerosis.
Digestibility of pentose sugars and uronic acids and their effect on chick weight gain and caecal size.
[Anti-alpha-gliadin antibodies. Sensitivity, specificity and correlation with blood xylose test in the 3 diagnostic stages of celiac disease in children].
Chemically induced bowel denervation improves survival in short bowel syndrome.
Enteral versus parenteral therapy for intractable diarrhea of infancy: a prospective, randomized trial.
[Enteral resorption kinetics in the aging process].
Protracted diarrhea in infancy: clinical aspects and ultrastructural analysis of the small intestine.
Use of D-xylose to detect ingestion of a powdered milk food supplement by family members other than the children 0-2 years of age for whom it was intended.
Age-dependent alterations of intestinal absorption. II. A clinical study using a modified D-xylose absorption test.
Atypical biogroups of Escherichia coli found in clinical specimens and description of Escherichia hermannii sp. nov.
Serum D-xylose absorption tests: reproducibility and diagnostic usefulness in food-induced enterocolitis.
The effect of dietary fibre on D-xylose absorption.
[Postoperative small intestinal resorption after retropubic extravesical bladder neck adenomectomy (Millin)].
Distinctions among three sugars in their effects on gastric emptying and satiety.
[Enteric resorption of an oral, balanced synthetic diet (Berlamin). Clinical experimental study using the modified D-xylose resorption test].
[Enteral resorption and tumor cachexia].
Immunological studies of eosinophilic gastro-enteritis and treatment with disodium cromoglycate and beclomethasone dipropionate.
Investigation of reserve functional ability of small intestine by xylose test after food loading.
Intestinal bypass surgery for obesity decreases food intake and taste preferences.
[d-Xylose test after food loading as a method of functional study of the small intestine].
[Assessment of intestinal absorption by means of d-xylose test in patients with asthma with reference to skin tests for alimentary allergens].
D-Xylose excretion--a test for tropical sprue in children and as a tracer for dietary supplementation.

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):	View
CHEBI:	View
CHEMBL:	View
Golm Metabolome Database:	Search
Metabolomics Database:	Search
KEGG (GenomeNet):	C00181
HMDB (The Human Metabolome Database):	HMDB00098
FooDB:	FDB001136
YMDB (Yeast Metabolome Database):	YMDB00779
Export Tariff Code:	2940.00.6000
FDA Listing of Food Additive Status:	View
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
Formulations/Preparations: grades: reagent, technical

Suppliers

Alfa Biotechnology	BOC Sciences
Carbosynth	ECSA Chemicals
EMD Millipore	ExtraSynthese
Glentham Life Sciences	H. Interdonati, Inc.
Lluch Essence	O'Laughlin Industries
Penta International	Prinova
Qingdao Dacon Trading	Santa Cruz Biotechnology
Sigma-Aldrich	Sinofi Food Ingredients
Synerzine	TCI AMERICA
United International	Penta International Corporation
Qingdao Free Trade Zone United International Co Ltd

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	150.13070678711
Melting Point	154 to 158°C @ 760 mm Hg
Boiling Point	90 to 91°C @ 760 mm Hg
Flash Point TCC Value	155.3 °C TCC
logP (o/w)	-1.98
Solubility
water, 5.55E+05 mg/L @ 25 °C (exp)	Yes

Organoleptic Properties

Odor Type: Smoky
smoky, woody, sweet, caramellic
Odor strength	low
Substantivity	285 hour(s) at 10.00 % in dipropylene glycol
Luebke, William tgsc, (1989)	At 100.00 %. smoky woody sweet caramel
Flavor Type: Smoky
smoky, sweet, salty, coffee
Luebke, William tgsc, (1989)	Smoky sweet salty coffee

Occurrences

Potential Uses

Applications	sweeteners flavor enhancers
Odor purposes	Leather , Woody
Flavoring purposes	Smoke , Sweet
Cosmetic purposes	Fragrance , Humectants , Skin conditioning

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children. S 22 - Do not breath dust. S 24/25 - Avoid contact with skin and eyes.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 23000 mg/kg Yakkyoku. Pharmacy. Vol. 32, Pg. 1367, 1981. intravenous-mouse LD50 11300 mg/kg Yakkyoku. Pharmacy. Vol. 32, Pg. 1367, 1981.
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
sweeteners, flavor enhancers
Recommendation for dextro-xylose usage levels up to:
	not for fragrance use.

Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 12
Click here to view publication 12
		average usual ppm	average maximum ppm
baked goods:		-	-
beverages(nonalcoholic):		-	-
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	-
fruit ices:		-	-
gelatins / puddings:		-	-
granulated sugar:		-	-
gravies:		-	40.00000
hard candy:		-	-
imitation dairy:		-	-
instant coffee / tea:		-	-
jams / jellies:		-	-
meat products:		-	-
milk products:		-	-
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		-	-
processed vegetables:		-	-
reconstituted vegetables:		-	85.00000
seasonings / flavors:		-	40.00000
snack foods:		-	60.00000
soft candy:		-	-
soups:		-	-
sugar substitutes:		-	-
sweet sauces:		-	-

Safety references

EPI System: View

ClinicalTrials.gov:search

Chemical Carcinogenesis Research Information System:Search

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):58-86-6

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :6027

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:2

(2S,3R,4S,5R)-oxane-2,3,4,5-tetrol

Chemidplus:0000058866

RTECS:ZF2285000 for cas# 58-86-6