| Name: | (2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol |
| CAS Number: | 585-99-9 |  3D/inchi
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| ECHA EINECS - REACH Pre-Reg: | 209-568-6 |
| FDA UNII: | 9B1VBE526I |
| MDL: | MFCD00198188 |
| XlogP3-AA: | -4.70 (est) |
| Molecular Weight: | 342.29854000 |
| Formula: | C12 H22 O11 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:humectants
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 662.80 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 670.00 °F. TCC ( 354.60 °C. ) (est)
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| logP (o/w): | -3.200 (est) |
| 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 |
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| 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 | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | humectants |
| Recommendation for melibiose usage levels up to: | | | not for fragrance use.
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| |
| Recommendation for melibiose flavor usage levels up to: |
| | not for flavor use.
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Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):585-99-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :11458 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol |
| Chemidplus:0000585999 |
References:
| | (2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 585-99-9 |
| Pubchem (cid): | 11458 |
| Pubchem (sid): | 134975774 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| D- | glucose, 6-O-alpha-D-galactopyranosyl- | | D- | melibiose | | alpha-dextro- | melibiose hydrate | | (2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5- | trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol |
Articles:
| PubMed:A new α-galactosidase from thermoacidophilic Alicyclobacillus sp. A4 with wide acceptor specificity for transglycosylation. |
| PubMed:Phenotypes of Escherichia coli isolated from urine: Differences between extended-spectrum β-lactamase producers and sensitive strains. |
| PubMed:Dickeya aquatica sp. nov., isolated from waterways. |
| PubMed:Characterization of α-galacto-oligosaccharides formed via heterologous expression of α-galactosidases from Lactobacillus reuteri in Lactococcus lactis. |
| PubMed:Global characterization of neutral saccharides in crude and processed Radix Rehmanniae by hydrophilic interaction liquid chromatography tandem electrospray ionization time-of-flight mass spectrometry. |
| PubMed:Genotype-phenotype matching analysis of 38 Lactococcus lactis strains using random forest methods. |
| PubMed:The effect of selected synbiotics on microbial composition and short-chain fatty acid production in a model system of the human colon. |
| PubMed:Functional analysis of family GH36 α-galactosidases from Ruminococcus gnavus E1: insights into the metabolism of a plant oligosaccharide by a human gut symbiont. |
| PubMed:Levansucrase and sucrose phoshorylase contribute to raffinose, stachyose, and verbascose metabolism by lactobacilli. |
| PubMed:NMR characterization of saccharides in Italian honeys of different floral sources. |
| PubMed:Purification and characterization of α-galactosidase from white chickpea (Cicer arietinum). |
| PubMed:Characterization of a protease-resistant α-galactosidase from the thermophilic fungus Rhizomucor miehei and its application in removal of raffinose family oligosaccharides. |
| PubMed:Population structure of the Yersinia pseudotuberculosis complex according to multilocus sequence typing. |
| PubMed:α-Galactosidase/sucrose kinase (AgaSK), a novel bifunctional enzyme from the human microbiome coupling galactosidase and kinase activities. |
| PubMed:Study of influential factors on oligosaccharide formation by fructosyltransferase activity during stachyose hydrolysis by Pectinex ultra SP-L. |
| PubMed:Purification and characterization of Aspergillus terreus α-galactosidases and their use for hydrolysis of soymilk oligosaccharides. |
| PubMed:Isolation and characterization of lactic acid bacteria strains with ornithine producing capacity from natural sea salt. |
| PubMed:An alpha-galactosidase from an acidophilic Bispora sp. MEY-1 strain acts synergistically with beta-mannanase. |
| PubMed:Biological diversity of Saccharomyces yeasts of spontaneously fermenting wines in four wine regions: comparative genotypic and phenotypic analysis. |
| PubMed:A food-grade industrial arming yeast expressing beta-1,3-1,4-glucanase with enhanced thermal stability. |
| PubMed:NMR studies on the interaction of sugars with the C-terminal domain of an R-type lectin from the earthworm Lumbricus terrestris. |
| PubMed:A novel protease-resistant alpha-galactosidase with high hydrolytic activity from Gibberella sp. F75: gene cloning, expression, and enzymatic characterization. |
| PubMed:Debaryomyces hansenii UFV-1 intracellular alpha-galactosidase characterization and comparative studies with the extracellular enzyme. |
| PubMed:A novel alpha-galactosidase from Bifidobacterium bifidum with transgalactosylating properties: gene molecular cloning and heterologous expression. |
| PubMed:Sugar fermentation in probiotic bacteria--an in vitro study. |
| PubMed:Preparation and biological properties of a melibiose binding lectin from Bauhinia variegata seeds. |
| PubMed:Reduction of soybean oligosaccharides and properties of alpha-D-galactosidase from Lactobacillus curvatus R08 and Leuconostoc mesenteroides [corrected] JK55. |
| PubMed:Enterobacter pulveris sp. nov., isolated from fruit powder, infant formula and an infant formula production environment. |
| PubMed:Luteimonas composti sp. nov., a moderately thermophilic bacterium isolated from food waste. |
| PubMed:A food-grade expression/secretion vector for Lactococcus lactis that uses an alpha-galactosidase gene as a selection marker. |
| PubMed:Construction and evaluation of food-grade vectors for Lactococcus lactis using aspartate aminotransferase and alpha-galactosidase as selectable markers. |
| PubMed:Extracellular alpha-galactosidase from Debaryomyces hansenii UFV-1 and its use in the hydrolysis of raffinose oligosaccharides. |
| PubMed:A chromogenic plating medium for the isolation and identification of Enterobacter sakazakii from foods, food ingredients, and environmental sources. |
| PubMed:Increasing the transglycosylation activity of alpha-galactosidase from Bifidobacterium adolescentis DSM 20083 by site-directed mutagenesis. |
| PubMed:Sugar convertibility in the parasitoid Cotesia glomerata (Hymenoptera: Braconidae). |
| PubMed:Use of an alpha-galactosidase gene as a food-grade selection marker for Streptococcus thermophilus. |
| PubMed:An apoptotic inducer, aralin, is a novel type II ribosome-inactivating protein from Aralia elata. |
| PubMed:Molecular analysis of artisanal Italian cheeses reveals Enterococcus italicus sp. nov. |
| PubMed:Analysis of reducing carbohydrates by reductive tryptamine derivatization prior to micellar electrokinetic capillary chromatography. |
| PubMed:Cloning and expression of sucrose phosphorylase gene from Bifidobacterium longum in E. coli and characterization of the recombinant enzyme. |
| PubMed:In vitro evaluation of the fermentation properties of galactooligosaccharides synthesised by alpha-galactosidase from Lactobacillus reuteri. |
| PubMed:Synthesis of alpha-galactooligosaccharides with alpha-galactosidase from Lactobacillus reuteri of canine origin. |
| PubMed:Different food sources affect the gustatory response of Anaphes iole, an egg parasitoid of Lygus Spp. |
| PubMed:Gustatory perception and metabolic utilization of sugars by Myrmica rubra ant workers. |
| PubMed:Novel food-grade plasmid vector based on melibiose fermentation for the genetic engineering of Lactococcus lactis. |
| PubMed:Purification and characterization of a thermostable alpha-galactosidase from Thermoanaerobacterium polysaccharolyticum. |
| PubMed:New efficient amylase-producing strains of Lactobacillus plantarum and L. fermentum isolated from different Nigerian traditional fermented foods. |
| PubMed:Soy molasses as fermentation substrate for production of butanol using Clostridium beijerinckii BA101. |
| PubMed:A comparison of nectar- and honeydew sugars with respect to their utilization by the hymenopteran parasitoid Cotesia glomerata. |
| PubMed:Characterization of two novel saccharolytic, anaerobic thermophiles, Thermoanaerobacterium polysaccharolyticum sp. nov. and Thermoanaerobacterium zeae sp. nov., and emendation of the genus Thermoanaerobacterium. |
| PubMed:Influence of lipids with and without other cottonseed reserve materials on aflatoxin B(1) production by Aspergillus flavus. |
| PubMed:Epidemiologic typing of Salmonella enterica serotype enteritidis in a Canada-wide outbreak of gastroenteritis due to contaminated cheese. |
| PubMed:The microbial association of Greek taverna sausage stored at 4 and 10 degrees C in air, vacuum or 100% carbon dioxide, and its spoilage potential. |
| PubMed:Transglycosidase activity of Bifidobacterium adolescentis DSM 20083 alpha-galactosidase. |
| PubMed:Engineering baker's yeast: room for improvement. |
| PubMed:Characterization of lactococci isolated from minimally processed fresh fruit and vegetables. |
| PubMed:Acceptor specificity of cellobiose phosphorylase from Cellvibrio gilvus: synthesis of three branched trisaccharides. |
| PubMed:Thermostable alpha-galactosidase from Thermotoga neapolitana: cloning, sequencing and expression. |
| PubMed:Substrate specificities of Penicillium simplicissimum alpha-galactosidases. |
| PubMed:Factors regulating production of alpha-galactosidase from Bacillus sp. JF2. |
| PubMed:Purification and partial characterization of an antigen specific to Lactobacillus brevis strains with beer spoilage activity. |
| PubMed:[Identification of Citrobacter species and their occurrence in raw products and foods]. |
| PubMed:Three alpha-galactosidase genes of Trichoderma reesei cloned by expression in yeast. |
| PubMed:Biochemical characterization of lactobacilli from dry fermented sausages. |
| PubMed:Numerical taxonomy of gram-negative, nonmotile, nonfermentative bacteria isolated during chilled storage of lamb carcasses. |
| PubMed:Phage typing of Salmonella enteritidis in the United States. |
| PubMed:Antibody response to haptenic sugar antigen: immunodominancy of protein-bound lactose formed by amino-carbonyl reaction. |
| PubMed:Conventional taxonomy of lactobacilli surviving radurization of meat. |
| PubMed:[Serotype characterization of Escherichia coli potentially producing enterotoxins in foods]. |
| PubMed:Biochemical differentiation between enterotoxigenic heat-sensitive and heat-resistant Clostridium perfringens strains. |
| PubMed:[Effects of soluble carbohydrates from several tropical foods (cassava, peanuts, coconut and papaya) on calcium utilization in the rat]. |
| PubMed:Isolation and characteristics of Yersinia enterocolitica-like bacteria from meats. |
| PubMed:Lactobacilli isolated from French saucisson (taxonomic study). |
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Isol. from coffee beans, apple (Pyrus malus) and other plants
Melibiose is disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes. It is not an endogenous metabolite but may be obtained from the consumption of partially fermented molasses, brown sugar or honey. Antibodies to melibiose will appear in individuals affected by Chagas' disease (Trypanosoma cruzi infection). Melibiose is not metabolized by humans, but can be broken down by gut microflora, such as E. coli. In fact, E. coli is able to utilize melibiose as a sole source of carbon. Melibiose is first imported by the melibiose permease, MelB and then converted to β-D-glucose and β-D-galactose by the α-galactosidase encoded by melA. Because of its poor digestability Melibiose (along with rhamnose) can be used together for noninvasive intestinal mucosa barrier testing. This test can be used to assess malabsorption or impairment of intestinal permeability. Recent studies with dietary melibiose have shown that can strongly affected the Th cell responses to an ingested antigen. It has been suggested that melibiose could be used to enhance the induction of oral tolerance. (PMID 17986780)
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