EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

laevo-xylulose
L-threo-2-pentulose

Supplier Sponsors

CAS Number: 527-50-4Picture of molecule3D/inchi
Other(deleted CASRN):1501947-94-9
FDA UNII: DL1M07LQ7A
Nikkaji Web:J13.211J
MDL:MFCD00075347
XlogP3-AA:-2.60 (est)
Molecular Weight:150.13070000
Formula:C5 H10 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 469.10 °C. @ 760.00 mm Hg (est)
Flash Point:> 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w): -1.200 (est)
Soluble in:
 water, 5.528e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
L-Xylulose - Aqueous solution
Carbosynth
For experimental / research use only.
L-Xylulose - Aqueous solution
Santa Cruz Biotechnology
For experimental / research use only.
L-Xylulose ∼95%
Sigma-Aldrich: Sigma
For experimental / research use only.
L-Xylulose ∼95%, syrup
sds
 
Safety Information:
Preferred SDS: View
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for laevo-xylulose usage levels up to:
 not for fragrance use.
 
Recommendation for laevo-xylulose flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :22253
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(3R,4S)-1,3,4,5-tetrahydroxypentan-2-one
Chemidplus:0000527504
 
References:
 (3R,4S)-1,3,4,5-tetrahydroxypentan-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):22253
Pubchem (sid):135250238
 
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
CHEBI:View
KEGG (GenomeNet):C00312
HMDB (The Human Metabolome Database):HMDB00751
FooDB:FDB022223
Export Tariff Code:2940.00.0000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
L-threo-2-pentulose
(3R,4S)-1,3,4,5-tetrahydroxypentan-2-one
L-xylulose
 

Articles:

PubMed:Proteomic identification of target proteins in normal but nonfertilizing sperm.
PubMed:Human DCXR - another 'moonlighting protein' involved in sugar metabolism, carbonyl detoxification, cell adhesion and male fertility?
PubMed:pH-rate profiles of L-arabinitol 4-dehydrogenase from Hypocrea jecorina and its application in L-xylulose production.
PubMed:Immobilization of L-arabinitol dehydrogenase on aldehyde-functionalized silicon oxide nanoparticles for L-xylulose production.
PubMed:Dicarbonyl/l-xylulose reductase (DCXR): The multifunctional pentosuria enzyme.
PubMed:(-)-Epigallocatechin-3-gallate, a potential inhibitor to human dicarbonyl/L-xylulose reductase.
PubMed:A novel L-xylulose reductase essential for L-arabinose catabolism in Trichoderma reesei.
PubMed:Gene cloning and characterization of L-ribulose 3-epimerase from Mesorhizobium loti and its application to rare sugar production.
PubMed:NAD⁺-dependent xylitol dehydrogenase (xdhA) and L-arabitol-4-dehydrogenase (ladA) deletion mutants of Aspergillus oryzae for improved xylitol production.
PubMed:Xylanase gene transcription in Trichoderma reesei is triggered by different inducers representing different hemicellulosic pentose polymers.
PubMed:Respiratory and olfactory cytotoxicity of inhaled 2,3-pentanedione in Sprague-Dawley rats.
PubMed:Production of L-xylose from L-xylulose using Escherichia coli L-fucose isomerase.
PubMed:Garrod's fourth inborn error of metabolism solved by the identification of mutations causing pentosuria.
PubMed:L-arabitol is the actual inducer of xylanase expression in Hypocrea jecorina (Trichoderma reesei).
PubMed:DHS-21, a dicarbonyl/L-xylulose reductase (DCXR) ortholog, regulates longevity and reproduction in Caenorhabditis elegans.
PubMed:Gene expression in the epididymis of normal and vasectomized men: what can we learn about human sperm maturation?
PubMed:Bioinformatic and biochemical characterization of DCXR and DHRS2/4 from Caenorhabditis elegans.
PubMed:Covalent immobilization of recombinant Rhizobium etli CFN42 xylitol dehydrogenase onto modified silica nanoparticles.
PubMed:Fungal arabinan and L-arabinose metabolism.
PubMed:Cloning and overexpression of the xylitol dehydrogenase gene from Bacillus pallidus and its application to L-xylulose production.
PubMed:Characterization of a recombinant thermostable L: -rhamnose isomerase from Thermotoga maritima ATCC 43589 and its application in the production of L-lyxose and L-mannose.
PubMed:Structure and engineering of L-arabinitol 4-dehydrogenase from Neurospora crassa.
PubMed:The 'true' L-xylulose reductase of filamentous fungi identified in Aspergillus niger.
PubMed:Cloning, characterization, and engineering of fungal L-arabinitol dehydrogenases.
PubMed:Molecular modeling studies of L-arabinitol 4-dehydrogenase of Hypocrea jecorina: its binding interactions with substrate and cofactor.
PubMed:Investigation of the effect of nitrogen on severity of Fusarium head blight in barley.
PubMed:[Unexpected in vitro fertilization failure in patients with normal sperm: a proteomic analysis].
PubMed:[Progress in the studies of human epididymal secretive proteins].
PubMed:Factors affecting the production of L-xylulose by resting cells of recombinant Escherichia coli.
PubMed:Microbial production of xylitol from L-arabinose by metabolically engineered Escherichia coli.
PubMed:Structure/function analysis of a critical disulfide bond in the active site of L-xylulose reductase.
PubMed:The Hypocrea jecorina (syn. Trichoderma reesei) lxr1 gene encodes a D-mannitol dehydrogenase and is not involved in L-arabinose catabolism.
PubMed:Open-closed conformational change revealed by the crystal structures of 3-keto-L-gulonate 6-phosphate decarboxylase from Streptococcus mutans.
PubMed:Structure of L-xylulose-5-Phosphate 3-epimerase (UlaE) from the anaerobic L-ascorbate utilization pathway of Escherichia coli: identification of a novel phosphate binding motif within a TIM barrel fold.
PubMed:Use of in vivo 13C nuclear magnetic resonance spectroscopy to elucidate L-arabinose metabolism in yeasts.
PubMed:L-Xylulose reductase is involved in 9,10-phenanthrenequinone-induced apoptosis in human T lymphoma cells.
PubMed:Dicarbonyl/L-xylulose reductase: a potential biomarker identified by laser-capture microdissection-micro serial analysis of gene expression of human prostate adenocarcinoma.
PubMed:Suppression of renal alpha-dicarbonyl compounds generated following ureteral obstruction by kidney-specific alpha-dicarbonyl/L-xylulose reductase.
PubMed:Expression of dicarbonyl/L-xylulose reductase (DCXR) in human skin and melanocytic lesions: morphological studies supporting cell adhesion function of DCXR.
PubMed:Epididymal P34H protein deficiency in men evaluated for infertility.
PubMed:Biochemical characterization of an L-Xylulose reductase from Neurospora crassa.
PubMed:Suppression of AGE precursor formation following unilateral ureteral obstruction in mouse kidneys by transgenic expression of alpha-dicarbonyl/L-xylulose reductase.
PubMed:[Preparation and identification of anti-human epididymal sperm protein P34H monoclonal antibody].
PubMed:Membranous and structural damage that occur during cryopreservation of human sperm may be time-related events.
PubMed:[Preparation and characterization of monoclonal antibody against DCXR].
PubMed:Levels of P34H, a sperm protein of epididymal origin, as a predictor of conventional in vitro fertilization outcome.
PubMed:Multiplicity of mammalian reductases for xenobiotic carbonyl compounds.
PubMed:Cloning and expression of a xylitol-4-dehydrogenase gene from Pantoea ananatis.
PubMed:Novel ligands for the extracellular solute receptors of two bacterial TRAP transporters.
PubMed:Transgenic mice over-expressing dicarbonyl/L-xylulose reductase gene crossed with KK-Ay diabetic model mice: an animal model for the metabolism of renal carbonyl compounds.
PubMed:Metabolic control analysis of Aspergillus niger L-arabinose catabolism.
PubMed:Structure of the tetrameric form of human L-Xylulose reductase: probing the inhibitor-binding site with molecular modeling and site-directed mutagenesis.
PubMed:Deletion of the yiaMNO transporter genes affects the growth characteristics of Escherichia coli K-12.
PubMed:[Construction of recombinant expression vector and prokaryotic expression of human epididymal sperm protein P34H].
PubMed:Structure-based discovery of human L-xylulose reductase inhibitors from database screening and molecular docking.
PubMed:Novel reactions of L-rhamnose isomerase from Pseudomonas stutzeri and its relation with D-xylose isomerase via substrate specificity.
PubMed:P26h and dicarbonyl/L-xylulose reductase are two distinct proteins present in the hamster epididymis.
PubMed:Male fertility markers, myth or reality.
PubMed:Evidence of newly generated neurons in the human olfactory bulb.
PubMed:Evolution of enzymatic activities in the orotidine 5'-monophosphate decarboxylase suprafamily: crystallographic evidence for a proton relay system in the active site of 3-keto-L-gulonate 6-phosphate decarboxylase.
PubMed:Evolution of enzymatic activities in the orotidine 5'-monophosphate decarboxylase suprafamily: mechanistic evidence for a proton relay system in the active site of 3-keto-L-gulonate 6-phosphate decarboxylase.
PubMed:Crystal structure of human L-xylulose reductase holoenzyme: probing the role of Asn107 with site-directed mutagenesis.
PubMed:Different clinical and morphological phenotypes in monozygotic twins with identical DCX mutation.
PubMed:A novel NADH-linked l-xylulose reductase in the l-arabinose catabolic pathway of yeast.
PubMed:Functional characterization of the Escherichia coli K-12 yiaMNO transport protein genes.
PubMed:Structural evidence for a 1,2-enediolate intermediate in the reaction catalyzed by 3-keto-L-gulonate 6-phosphate decarboxylase, a member of the orotidine 5'-monophosphate decarboxylase suprafamily.
PubMed:Tetrahydrobiopterin is synthesized from 6-pyruvoyl-tetrahydropterin by the human aldo-keto reductase AKR1 family members.
PubMed:Structural determinant for cold inactivation of rodent L-xylulose reductase.
PubMed:Production of ethanol from L-arabinose by Saccharomyces cerevisiae containing a fungal L-arabinose pathway.
PubMed:[Molecular cloning of human sperm surface protein P34H gene and semi-quantitative analysis of its expression in testis and epididymidis].
PubMed:Structure-based design of inhibitors of human L-xylulose reductase modelled into the active site of the enzyme.
PubMed:Identification of amino acid residues involved in substrate recognition of L-xylulose reductase by site-directed mutagenesis.
PubMed:[Epididymal sperm protein P34H and male reproduction].
PubMed:Crystallization and preliminary crystallographic analysis of human L-xylulose reductase.
PubMed:The missing link in the fungal L-arabinose catabolic pathway, identification of the L-xylulose reductase gene.
PubMed:Molecular characterization of mammalian dicarbonyl/L-xylulose reductase and its localization in kidney.
PubMed:Substrate specificity and kinetic mechanism of Escherichia coli ribulokinase.
PubMed:Utilization of L-ascorbate by Escherichia coli K-12: assignments of functions to products of the yjf-sga and yia-sgb operons.
PubMed:Cloning and expression of a fungal L-arabinitol 4-dehydrogenase gene.
PubMed:Molecular cloning, expression and tissue distribution of hamster diacetyl reductase. Identity with L-xylulose reductase.
PubMed:Membrane-bound sugar alcohol dehydrogenase in acetic acid bacteria catalyzes L-ribulose formation and NAD-dependent ribitol dehydrogenase is independent of the oxidative fermentation.
PubMed:Effect of vasectomy on P34H messenger ribonucleic acid expression along the human excurrent duct: a reflection on the function of the human epididymis.
PubMed:Role of the yiaR and yiaS genes of Escherichia coli in metabolism of endogenously formed L-xylulose.
PubMed:Regulation of expression of the yiaKLMNOPQRS operon for carbohydrate utilization in Escherichia coli: involvement of the main transcriptional factors.
PubMed:P34H sperm protein is preferentially expressed by the human corpus epididymidis.
PubMed:[Essential pentosuria].
PubMed:Inhibition of glycoprotein processing by L-fructose and L-xylulose.
PubMed:Accumulation of xylitol in the mammalian lens is related to glucuronate metabolism.
PubMed:Structural studies of O-specific polysaccharide chains of the lipopolysaccharide from Yersinia enterocolitica serovar O:10.
PubMed:Activation of a cryptic gene encoding a kinase for L-xylulose opens a new pathway for the utilization of L-lyxose by Escherichia coli.
PubMed:Extracellular arabinases in Aspergillus nidulans: the effect of different cre mutations on enzyme levels.
PubMed:L-lyxose metabolism employs the L-rhamnose pathway in mutant cells of Escherichia coli adapted to grow on L-lyxose.
PubMed:Human L-xylulose reductase variation: family and population studies.
PubMed:Inducible xylitol dehydrogenases in enteric bacteria.
PubMed:On the nature of L-xylulose reductase deficiency in essential pentosuria.
PubMed:Characterization of xylitol-utilizing mutants of Erwinia uredovora.
PubMed:A Japanese case of pentosuria.
PubMed:Production of D- and L-xylulose by mutants of Klebsiella pneumoniae and Erwinia uredovora.
PubMed:Directed evolution of a second xylitol catabolic pathway in Klebsiella pneumoniae.
PubMed:Elevated L-xylulose concentrations in serum: a difference between type I and type II diabetes.
PubMed:Increased urinary excretion of L-xylulose in patients with liver cirrhosis.
PubMed:The stereospecificity of sequential nicotinamide-adenine dinucleotide-dependent oxidoreductases in relation to the evolution of metabolic sequences.
PubMed:Influence of lead administration on L-ascorbic acid metabolism in rats: effect of L-ascorbic acid supplementation.
PubMed:Growth of Aerobacter aerogenes on D-arabinose: origin of the enzyme activities.
PubMed:[On the occurrence and activity of xylitol:NADO-oxidoreductase (L-xylulose-forming) in vertebrates].
PubMed:Diabetic angiopathy and L-xylulose.
PubMed:L-xylulose metabolism in diabetes mellitus.
PubMed:Regulation of ascorbic acid and of xylulose synthesis in rat-liver extracts. The effect of alloxan-diabetes on the glucuronic acid pathway.
PubMed:L-XYLULOSE CONCENTRATIONS IN SERA OF DIABETIC PATIENTS.
PubMed:Enzymic formation of L-xylulose from beeta-keto-L-gulonic acid.
PubMed:L-Xylulokinase and L-xylulose 5-phosphate-L-robulose 5-phosphate 3-epimerase in Aero-bacter aerogenes.
PubMed:Formation of L-xylulose from L-gulonic acid in rat kidney.
PubMed:Studies of the mechanism of L-xylulose formation by kidney enzymes.
PubMed:The enzymic conversion of D-glucuronate to L-ascorbate and L-xylulose in animal tissues.
PubMed:The conversion of 1-13C-D-glucuronolactone to 5-13C-L-xylulose in a pentosuric human.
PubMed:The L-xylulose-xylitol enzyme and other polyol dehydrogenases of guinea pig liver mitochondria.
PubMed:The reduction of L-xylulose to xylitol by guinea pig liver mitochondria.
PubMed:The influence of D-glucuronolactone on the excretion of L-xylulose by humans and guinea pigs.
PubMed:The identification of ribulose and L-xylulose in human and rat urine.
 
Notes:
Xylulose is a ketopentose - a monosaccharide containing five carbon atoms, and including a ketone functional group. It has chemical formula C5H10O5. In nature it occurs in the L- and D- isomers. L-xylulose accumulates in the urine of pentosuria patients. Since L-xylulose is a reducing sugar like D-glucose, pentosuria patients have been wrongly diagnosed in the past to be diabetic. [HMDB]
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