laevo-(+)-fructose
L-(+)-fructose
Identification
| Name | laevo-(+)-fructose |
| IUPAC | (3R,4S,5S)-1,3,4,5,6-pentahydroxyhexan-2-one |
| CAS Number | 7776-48-9 |
| FDA UNII | ZJ8X2IF6RJ |
| Molecular Formula | C6 H12 O6 |
| Molecular Weight | 180.15684000 |
| MDL Number | MFCD05662378 |
| Nikkaji Number | J363.054D |
| Beilstein | 1724560 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Flash Point | 32.00 °F. TCC ( 0.00 °C. ) (est) |
| Soluble in | water, 9.769e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for laevo-(+)-fructose usage levels up to | not for fragrance use. |
| Recommendation for laevo-(+)-fructose flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
keto-L-
fructose
L-(+)-
fructose
(3R,4S,5S)-1,3,4,5,6-
pentahydroxyhexan-2-one
PubMed:
Extra fructose in the growth medium fuels lipogenesis of adipocytes.
PubMed:
Maternal fructose intake during pregnancy modulates hepatic and hypothalamic AMP-activated protein kinase signalling in a sex-specific manner in offspring.
PubMed:
Fructose stimulates Na/H exchange activity and sensitizes the proximal tubule to angiotensin II.
PubMed:
Biosynthesis of rare hexoses using microorganisms and related enzymes.
PubMed:
Stuck fermentation: development of a synthetic stuck wine and study of a restart procedure.
PubMed:
Use of response surface methodology to study the effect of media composition on aflatoxin production by Aspergillus flavus.
PubMed:
Exploration of CHÂ·Â·Â·Ï mediated stacking interactions in saccharide: aromatic residue complexes through conformational sampling.
PubMed:
Enhanced antibiotic production by Streptomyces sindenensis using artificial neural networks coupled with genetic algorithm and Nelder-Mead downhill simplex.
PubMed:
Direct lactic acid fermentation of Jerusalem artichoke tuber extract using Lactobacillus paracasei without acidic or enzymatic inulin hydrolysis.
PubMed:
Boronic acid-protected gold clusters capable of asymmetric induction: spectral deconvolution analysis of their electronic absorption and magnetic circular dichroism.
PubMed:
Production of bioactive exopolysaccharides from bitter medicinal mushroom, Antrodia camphorata (M. Zang et C.H. Su) Sh.H. Wu et al. (Aphyllophoromycetideae) in submerged cultivation.
PubMed:
Enzymatic synthesis of D-sorbose and D-psicose with aldolase RhaD: effect of acceptor configuration on enzyme stereoselectivity.
PubMed:
Recognition of d-fructose based on tetra-boronic functionalized viologen in aqueous solution.
PubMed:
The effect of carbon source supplementation on the production of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) by Cupriavidus necator.
PubMed:
Assessment of sperm survival and functional membrane integrity of the six-banded armadillo (Euphractus sexcinctus).
PubMed:
Synthesis of rare sugars with L-fuculose-1-phosphate aldolase (FucA) from Thermus thermophilus HB8.
PubMed:
Sugar-based enantiomeric and conformationally constrained pyrrolo[2,1-c][1,4]-benzodiazepines as potential GABAA ligands.
PubMed:
Effects of mono- and disaccharides on the antimicrobial activity of bovine lactoperoxidase system.
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:
Crystallization and preliminary X-ray crystallographic analysis of L-rhamnose isomerase with a novel high thermostability from Bacillus halodurans.
PubMed:
Optimizing dilute-acid pretreatment of rapeseed straw for extraction of hemicellulose.
PubMed:
Effect of modified MRS medium on production and purification of antimicrobial peptide ST4SA produced by Enterococcus mundtii.
PubMed:
Parasympathetic dysfunction is associated with insulin resistance in fructose-fed female rats.
PubMed:
Effects of fructose and/or fat in the diet on developing the type 2 diabetic-like syndrome in CD-1 mice.
PubMed:
Submerged citric acid fermentation on orange peel autohydrolysate.
PubMed:
Cloning, sequencing, overexpression and characterization of L-rhamnose isomerase from Bacillus pallidus Y25 for rare sugar production.
PubMed:
Substrate spectrum of L-rhamnulose kinase related to models derived from two ternary complex structures.
PubMed:
[Influence of intravenous infusion of D-fructose on post-operative blood glucose level in burn patients].
PubMed:
Practical synthesis of an L-fructose-derived ketone catalyst for asymmetric epoxidation of olefins.
PubMed:
Efficient production of 2-deoxyribose 5-phosphate from glucose and acetaldehyde by coupling of the alcoholic fermentation system of Baker's yeast and deoxyriboaldolase-expressing Escherichia coli.
PubMed:
Structure and reaction mechanism of L-rhamnulose kinase from Escherichia coli.
PubMed:
Fructose metabolism in the adult mouse optic nerve, a central white matter tract.
PubMed:
Synthesis of the ABC tricyclic fragment of the pectenotoxins via stereocontrolled cyclization of a gamma-hydroxyepoxide appended to the AB spiroacetal unit.
PubMed:
A novel bioconversion of L-fructose to L-glucose by Klebsiella pneumoniae.
PubMed:
Production of L-sorbitol from L-fructose by Aureobasidium pullulans LP23 isolated from soy sauce mash.
PubMed:
[Media optimization for exopolysaccharide by Pholiota squarrosa (Pers. ex Fr.) Quel. AS 5.245 on submerged fermentation].
PubMed:
Defining conditions that lead to the retention of water: the importance of the arterial sodium concentration.
PubMed:
Fructose-mediated non-enzymatic glycation: sweet coupling or bad modification.
PubMed:
Novel reactions of L-rhamnose isomerase from Pseudomonas stutzeri and its relation with D-xylose isomerase via substrate specificity.
PubMed:
One-pot synthesis of L-Fructose using coupled multienzyme systems based on rhamnulose-1-phosphate aldolase.
PubMed:
Iodomethyl group as a hydroxymethyl synthetic equivalent: application to the syntheses of D-manno-hept-2-ulose and l-fructose derivatives.
PubMed:
Production of mannitol and lactic acid by fermentation with Lactobacillus intermedius NRRL B-3693.
PubMed:
Base catalysed isomerisation of aldoses of the arabino and lyxo series in the presence of aluminate.
PubMed:
Fructose intake increases hyperlipidemia and modifies apolipoprotein expression in apolipoprotein AI-CIII-AIV transgenic mice.
PubMed:
Bacterial cellulose production under oxygen-enriched air at different fructose concentrations in a 50-liter, internal-loop airlift reactor.
PubMed:
Photochemical deconjugation of chiral 3-methyl-2-butenoates derived from carbohydrate-based alcohols: the influence of the sugar backbone on the facial diastereoselectivity.
PubMed:
Bioenergetic targeting during organ preservation: (31)P magnetic resonance spectroscopy investigations into the use of fructose to sustain hepatic ATP turnover during cold hypoxia in porcine livers.
PubMed:
Aldol reactions on 1-deoxy-3,4:5,6-di-O-isopropylidene-L-fructose as a route to higher-carbon carbohydrates.
PubMed:
[The role of the carbohydrate composition of the glycocalyx in some species of lactobacilli in the manifestation of their adhesive properties].
PubMed:
Galactose consumption induces conditioned flavor avoidance in rats.
PubMed:
Isolation and characterization of Enterobacter cloacae capable of metabolizing asparagine.
PubMed:
Structure-activity studies on anticonvulsant sugar sulfamates related to topiramate. Enhanced potency with cyclic sulfate derivatives.
PubMed:
Effects of hypertonia on voltage-gated ion currents in freshly isolated hippocampal neurons, and on synaptic currents in neurons in hippocampal slices.
PubMed:
Inhibition of glycoprotein processing by L-fructose and L-xylulose.
PubMed:
Whole body metabolism is not restricted to D-sugars because energy metabolism of L-sugars fits a computational model in rats.
PubMed:
Vanadate treatment rapidly improves glucose transport and activates 6-phosphofructo-1-kinase in diabetic rat intestine.
PubMed:
Low dose fructose ingestion during gestation and lactation affects carbohydrate metabolism in rat dams and their offspring.
PubMed:
[The energetic utilization of L-fructose in rats].
PubMed:
Decreased Coomassie brilliant blue colour yield with glycated proteins.
PubMed:
Essential fructosuria: increased levels of fructose 3-phosphate in erythrocytes.
PubMed:
Homogeneous distribution of phosphofructokinase in the rat liver acinus: a quantitative histochemical study.
PubMed:
A comparative study of the glycosylated plasma proteins in diabetic Nigerians.
PubMed:
Glucose absorption from maltotriose and glucose oligomers in the human jejunum.
PubMed:
Effects of glucose and fructose added to the intraocular irrigating solutions on the rabbit ERG in vitro.
PubMed:
Continuous production of ethanol from fructose by immobilized growing cells of Zymomonas mobilis.
PubMed:
Comparative effects of glucose and fructose on growth and morphological aspects of cultured skin fibroblasts.
PubMed:
Crabtree effect induced by fructose in hepatocytes isolated from regenerating liver.
PubMed:
L-fructose.