| Name: | (2R,3R,4R,5R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal |
| CAS Number: | 41263-94-9 |  3D/inchi
|
| FDA UNII: | XO2533XO8R |
| Nikkaji Web: | J1.099.711I |
| MDL: | MFCD00079286 |
| XlogP3-AA: | -6.10 (est) |
| Molecular Weight: | 488.44104000 |
| Formula: | C18 H32 O15 |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:food additive
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Soluble in: |
| | water, 1e+006 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
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
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| Dermal Toxicity: |
|
Not determined
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| Inhalation Toxicity: |
|
Not determined
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Safety in Use Information:
| Category: | | food additive |
| Recommendation for 2'-fucosyl lactose usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for 2'-fucosyl lactose flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
European Food Safety Authority (EFSA) reference(s):
|
Safety of 2'-O-fucosyllactose as a novel food ingredient pursuant to Regulation (EC) No 258/97
View page or View pdf
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Statement on the safety of lacto-N-neotetraose and 2'-O-fucosyllactose as novel food ingredients in food supplements for children
View page or View pdf
|
Safety of 2’-fucosyllactose/difucosyllactose mixture as a novel food pursuant to Regulation (EU) 2015/2283
View page or View pdf
|
| 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 :170484 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (2R,3R,4R,5R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal |
| Chemidplus:0041263949 |
References:
| | (2R,3R,4R,5R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 170484 |
| Pubchem (sid): | 135126135 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| (2R,3R,4R,5R)-4-[(2S,3R,4S,5R,6R)-4,5- | dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal | | 2'- | fucosyllactose | | 2'-O- | fucosyllactose | | D- | glucose, O-6-deoxy-alpha-L-galactopyranosyl-(1-2)-O-beta-D-galactopyranosyl-(1-4)- |
Articles:
| PubMed:Structural characterisation of human galectin-4 C-terminal domain -elucidating the molecular basis for recognition of glycosphingolipids, sulfated saccharides and blood group antigens. |
| PubMed:Attenuation of food allergy symptoms following treatment with human milk oligosaccharides in a mouse model. |
| PubMed:Recognition of human milk oligosaccharides by bacterial exotoxins. |
| PubMed:Maternal fucosyltransferase 2 status affects the gut bifidobacterial communities of breastfed infants. |
| PubMed:In vitro impact of human milk oligosaccharides on enterobacteriaceae growth. |
| PubMed:Effects of a human milk oligosaccharide, 2'-fucosyllactose, on hippocampal long-term potentiation and learning capabilities in rodents. |
| PubMed:Fecal microbiota composition of breast-fed infants is correlated with human milk oligosaccharides consumed. |
| PubMed:Oligosaccharide composition of breast milk influences survival of uninfected children born to HIV-infected mothers in Lusaka, Zambia. |
| PubMed:A 3-week pre-clinical study of 2′-fucosyllactose in farm piglets. |
| PubMed:The human milk oligosaccharide 2'-fucosyllactose modulates CD14 expression in human enterocytes, thereby attenuating LPS-induced inflammation. |
| PubMed:Structure and substrate specificity of a eukaryotic fucosidase from Fusarium graminearum. |
| PubMed:Direct evidence for the presence of human milk oligosaccharides in the circulation of breastfed infants. |
| PubMed:Can an ancestral condition for milk oligosaccharides be determined? Evidence from the Tasmanian echidna (Tachyglossus aculeatus setosus). |
| PubMed:Fecal metabolomics of healthy breast-fed versus formula-fed infants before and during in vitro batch culture fermentation. |
| PubMed:Human milk oligosaccharides influence maturation of human intestinal Caco-2Bbe and HT-29 cell lines. |
| PubMed:Selective proliferation of intestinal Barnesiella under fucosyllactose supplementation in mice. |
| PubMed:Ultra high performance liquid chromatography-tandem mass spectrometry method for the determination of soluble milk glycans in rat serum. |
| PubMed:Pre-clinical safety evaluation of the synthetic human milk, nature-identical, oligosaccharide 2'-O-Fucosyllactose (2'FL). |
| PubMed:WbgL: a novel bacterial α1,2-fucosyltransferase for the synthesis of 2'-fucosyllactose. |
| PubMed:2'-fucosyllactose: an abundant, genetically determined soluble glycan present in human milk. |
| PubMed:Select human milk oligosaccharides directly modulate peripheral blood mononuclear cells isolated from 10-d-old pigs. |
| PubMed:Bioengineered 2'-fucosyllactose and 3-fucosyllactose inhibit the adhesion of Pseudomonas aeruginosa and enteric pathogens to human intestinal and respiratory cell lines. |
| PubMed:The human milk metabolome reveals diverse oligosaccharide profiles. |
| PubMed:Utilization of major fucosylated and sialylated human milk oligosaccharides by isolated human gut microbes. |
| PubMed:"Amide resonance" in the catalysis of 1,2-α-L-fucosidase from Bifidobacterium bifidum. |
| PubMed:Construction of Escherichia coli strains with chromosomally integrated expression cassettes for the synthesis of 2'-fucosyllactose. |
| PubMed:Neutral and acidic milk oligosaccharides of the striped skunk (Mephitidae: Mephitis mephitis). |
| PubMed:Human milk oligosaccharides inhibit rotavirus infectivity in vitro and in acutely infected piglets. |
| PubMed:In vitro fermentation characteristics of select nondigestible oligosaccharides by infant fecal inocula. |
| PubMed:Comprehensive profiles of human milk oligosaccharides yield highly sensitive and specific markers for determining secretor status in lactating mothers. |
| PubMed:The principal fucosylated oligosaccharides of human milk exhibit prebiotic properties on cultured infant microbiota. |
| PubMed:Lacto-N-tetraose, fucosylation, and secretor status are highly variable in human milk oligosaccharides from women delivering preterm. |
| PubMed:Bi- to tetravalent glycoclusters: synthesis, structure-activity profiles as lectin inhibitors and impact of combining both valency and headgroup tailoring on selectivity. |
| PubMed:Whole cell biosynthesis of a functional oligosaccharide, 2'-fucosyllactose, using engineered Escherichia coli. |
| PubMed:Development of biosensor-based assays to identify anti-infective oligosaccharides. |
| PubMed:Chemical characterization of milk oligosaccharides of an African lion (Panthera leo) and a clouded leopard (Neofelis nebulosa). |
| PubMed:Utilization of natural fucosylated oligosaccharides by three novel alpha-L-fucosidases from a probiotic Lactobacillus casei strain. |
| PubMed:Determination of sialyl and neutral oligosaccharide levels in transition and mature milks of Samoan women, using anthranilic derivatization followed by reverse phase high performance liquid chromatography. |
| PubMed:Fucosylated glycan inhibition of human hepatocellular carcinoma cell migration through binding to chemokine receptors. |
| PubMed:Two distinct alpha-L-fucosidases from Bifidobacterium bifidum are essential for the utilization of fucosylated milk oligosaccharides and glycoconjugates. |
| PubMed:Multivalent human blood group ABH and Lewis glycotopes are key recognition factors for a LFuc>Man binding lectin from phytopathogenic Ralstonia solanacearum. |
| PubMed:Improved determination of milk oligosaccharides using a single derivatization with anthranilic acid and separation by reversed-phase high-performance liquid chromatography. |
| PubMed:1,2-alpha-l-Fucosynthase: a glycosynthase derived from an inverting alpha-glycosidase with an unusual reaction mechanism. |
| PubMed:Structural basis of the catalytic reaction mechanism of novel 1,2-alpha-L-fucosidase from Bifidobacterium bifidum. |
| PubMed:Variation of major neutral oligosaccharides levels in human colostrum. |
| PubMed:Oligosaccharides in colostrum of Italian and Burkinabe women. |
| PubMed:Interactions of the fucose-specific Pseudomonas aeruginosa lectin, PA-IIL, with mammalian glycoconjugates bearing polyvalent Lewis(a) and ABH blood group glycotopes. |
| PubMed:Purification and characterization of extracellular 1,2-alpha-L-fucosidase from Bacillus cereus. |
| PubMed:The fucose-binding lectin from Ralstonia solanacearum. A new type of beta-propeller architecture formed by oligomerization and interacting with fucoside, fucosyllactose, and plant xyloglucan. |
| PubMed:An unusual anti-H lectin inhibited by milk from individuals with the Bombay phenotype. |
| PubMed:Molecular cloning and characterization of Bifidobacterium bifidum 1,2-alpha-L-fucosidase (AfcA), a novel inverting glycosidase (glycoside hydrolase family 95). |
| PubMed:Crystal structures of Erythrina cristagalli lectin with bound N-linked oligosaccharide and lactose. |
| PubMed:Characterization of oligosaccharides in milk of bearded seal (Erignathus barbatus). |
| PubMed:Differences in oligosaccharide pattern of a sample of polar bear colostrum and mid-lactation milk. |
| PubMed:Chemical characterization of the oligosaccharides in milk of high Arctic harbour seal (Phoca vitulina vitulina). |
| PubMed:[Studies of oligosaccharide specificity of perch roe fucolectin, using gold labeled neoglycoproteins]. |
| PubMed:Determination of each neutral oligosaccharide in the milk of Japanese women during the course of lactation. |
| PubMed:Cloning of a rat gene encoding the histo-blood group A enzyme. Tissue expression of the gene and of the A and B antigens. |
| PubMed:High-resolution crystal structures of Erythrina cristagalli lectin in complex with lactose and 2'-alpha-L-fucosyllactose and correlation with thermodynamic binding data. |
| PubMed:Chemical characterization of the oligosaccharides in beluga (Delphinapterus leucas) and Minke whale (Balaenoptera acutorostrata) milk. |
| PubMed:Comparison of oligosaccharides in milk specimens from humans and twelve other species. |
| PubMed:Synthesis of the milk oligosaccharide 2'-fucosyllactose using recombinant bacterial enzymes. |
| PubMed:Structural characterization of fucose-containing oligosaccharides by high-performance liquid chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. |
| PubMed:Chemical characterisation of the oligosaccharides in hooded seal (Cystophora cristata) and Australian fur seal (Arctocephalus pusillus doriferus) milk. |
| PubMed:Chemical characterization of milk oligosaccharides of the polar bear, Ursus maritimus. |
| PubMed:Structural basis of carbohydrate recognition by lectin II from Ulex europaeus, a protein with a promiscuous carbohydrate-binding site. |
| PubMed:A lectin from an edible mushroom Pleurotus ostreatus as a food intake-suppressing substance. |
| PubMed:Variability of human milk neutral oligosaccharides in a diverse population. |
| PubMed:Isolation and characterization from porcine serum of a soluble sulfotransferase responsible for 6-O-sulfation of the galactose residue in 2'-fucosyllactose: implications in the synthesis of the ligand for L-selectin. |
| PubMed:Chemical characterization of milk oligosaccharides of the Japanese black bear, Ursus thibetanus japonicus. |
| PubMed:Occurrence of an unusual lactose sulfate in dog milk. |
| PubMed:Purification and characterization of a lymph node sulfotransferase responsible for 6-O-sulfation of the galactose residues in 2'-fucosyllactose and other sialyl LewisX-related sugars. |
| PubMed:Fucosyltransferase activities in human pancreatic tissue: comparative study between cancer tissues and established tumoral cell lines. |
| PubMed:Identification of fucose alpha(1-2) galactose epitope-containing glycoproteins from rat hippocampus. |
| PubMed:Milk oligosaccharide profiles by reversed-phase HPLC of their perbenzoylated derivatives. |
| PubMed:Multiple fucosyltransferases and their carbohydrate ligands are involved in spermatogenic cell-Sertoli cell adhesion in vitro in rats. |
| PubMed:Identification of 2'-fucosyllactose in milk of the crabeater seal (Lobodon carcinophagus). |
| PubMed:Immobilized Lotus tetragonolobus agglutinin binds oligosaccharides containing the Le(x) determinant. |
| PubMed:Localized agglutinin staining in muscle capillaries from normal and very old atrophic human muscle using winged bean (Psophocarpus tetragonolobus) lectin. |
| PubMed:Thermodynamics of monosaccharide and disaccharide binding to Erythrina corallodendron lectin. |
| PubMed:Remodeling of mouse milk glycoconjugates by transgenic expression of a human glycosyltransferase. |
| PubMed:Glycosidic specificity of fucosyltransferases present in rat epididymal spermatozoa. |
| PubMed:Characterization of Biomphalaria alexandrina-derived lectins recognizing a fucosyllactose-related determinant on schistosomes. |
| PubMed:Presence of multiple fucosyltransferases in rat Sertoli cells and spermatogenic cells. |
| PubMed:Purification and characterization of alpha-L-fucosidase from Chinese hamster ovary cell culture supernatant. |
| PubMed:Fucose and fucose-containing sugar epitopes enhance hippocampal long-term potentiation in the freely moving rat. |
| PubMed:Lactose as affinity eluent and a synthetic sulfated copolymer as inhibitor, in conjunction with synthetic and natural acceptors, differentiate human milk Lewis-type and plasma-type alpha-L-fucosyltransferases. |
| PubMed:Purification and properties of the alpha-3/4-L-fucosyltransferase released into the culture medium during the growth of the human A431 epidermoid carcinoma cell line. |
| PubMed:Purification of the Lewis blood-group gene associated alpha-3/4-fucosyltransferase from human milk: an enzyme transferring fucose primarily to type 1 and lactose-based oligosaccharide chains. |
| PubMed:Assay of alpha 1,3 N-acetyl-D-galactosaminyl transferase by affinity chromatography. |
| PubMed:Variations in human liver fucosyltransferase activities in hepatobiliary diseases. |
| PubMed:Thermodynamic analysis of ligand binding to winged bean (Psophocarpus tetragonolobus) acidic agglutinin reveals its specificity for terminally monofucosylated H-reactive sugars. |
| PubMed:Complete purification and characterization of alpha-3-N-acetylgalactosaminyltransferase encoded by the human blood group A gene. |
| PubMed:Liquid ion-exchange chromatography under pressure of milk oligosaccharides using a pulsed amperometric detector. |
| PubMed:Separation of human milk oligosaccharides by recycling chromatography. First isolation of lacto-N-neo-difucohexaose II and 3'-Galactosyllactose from this source. |
| PubMed:Blood group ABO and Lewis antigens in bladder tumors: correlation between glycosyltransferase activity and antigen expression. |
| PubMed:Substrate specificity of fucosyltransferase purified from human parotid saliva. |
| PubMed:Studies on anti-H reagents. |
| PubMed:Characterisation of a blood-group A-active tetrasaccharide synthesised by a blood-group B gene-specified glycosyltransferase. |
| PubMed:Determination of the structures of fucosyl-lactose and difucosyl-lactose from the milk of monotremes, using 13C-n.m.r. spectroscopy. |
| PubMed:Regulatory mutations in CHO cells induce expression of the mouse embryonic antigen SSEA-1. |
| PubMed:A monoclonal antibody that precipitates the glycoprotein receptor for epidermal growth factor is directed against the human blood group H type 1 antigen. |
| PubMed:An enzyme basis for blood type A intermediate status. |
| PubMed:Purification of an almond emulsin fucosidase on Cibacron blue-sepharose and demonstration of its activity toward fucose-containing glycoproteins. |
| PubMed:A case of weak blood group B expression (Bm) associated with abnormal blood group galactosyltransferase. |
| PubMed:Abnormal blood group galactosyltransferase in blood type A1B-subjects whose sera contain anti-B agglutinin. |
| PubMed:Improved method for the isolation of 2' fucosyllactose from human milk. |
| PubMed:Human salivary fucosyltransferases : evidence for two distinct alpha-3-L-fucosyltransferase activities one or which is associated with the Lewis blood group Le gene. |
| PubMed:Membrane abnormality in red blood cells with weak type B expression. |
| PubMed:Probable biosynthetic pathway for the synthesis of the B antigen for Bh variants. |
| PubMed:A comparison of the alpha-L-fucosidase activities of human liver and serum. |
| PubMed:Porcine A blood group-specific N-acetylgalactosaminyltransferase. |
| PubMed:[Serum glycosyltransferase activity associated with antigen biosynthesis in blood groups A and B. Study of normal B group and cis AB group subjects]. |
| PubMed:Qualitative differences in the N-acetyl-D-galactosaminyltransferases produced by human A1 and A2 genes. |
| PubMed:N-acetyl-D-galactosaminyltransferase in human serum and erythrocyte membranes. |
| PubMed:Correlation between secretor status and the occurrence of 2'-fucosyllactose in human milk. |
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