rutinose
6-O-(alpha-L-rhamnosyl)-D-glucose
Identification
| Name | rutinose |
| IUPAC | (2R,3S,4S,5S)-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol |
| CAS Number | 90-74-4 |
| EINECS | 202-014-4 |
| FDA UNII | 0C4U3505G3 |
| Molecular Formula | C12 H22 O10 |
| Molecular Weight | 326.29934000 |
| MDL Number | MFCD00161473 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 190.50 °C. @ 760.00 mm Hg |
| Boiling Point | 598.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 600.00 °F. TCC ( 315.50 °C. ) (est) |
| logP (o/w) | -0.910 (est) |
| Soluble in | water, 1e+006 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 rutinose usage levels up to | not for fragrance use. |
| Recommendation for rutinose flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
6-O-(6-
deoxy-alpha-L-mannopyranosyl)-D-glucose
6-O-(alpha-L-
rhamnopyranosyl)-D-glucopyranose
6-O-(alpha-L-
rhamnosyl)-D-glucose
(2R,3S,4S,5S)-6-[[(2R,3R,4R,5R,6S)-3,4,5-
trihydroxy-6-methyloxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
PubMed:
Hesperidin Potentiates Ghrelin Signaling.
PubMed:
The occurrence, fate and biological activities of C-glycosyl flavonoids in the human diet.
PubMed:
Polyethyleneimine coating of magnetic particles increased the stability of an immobilized diglycosidase.
PubMed:
Identification and anti-oxidant capacity determination of phenolics and their glycosides in elderflower by on-line HPLC-CUPRAC method.
PubMed:
Direct detection of rutin-degrading isozymes with polyacrylamide gel electrophoresis.
PubMed:
Calculation of substrate binding affinities for a bacterial GH78 rhamnosidase through molecular dynamics simulations.
PubMed:
Targeting structural motifs of flavonoid diglycosides using collision-induced dissociation experiments on flavonoid/Pb2+ complexes.
PubMed:
Transglycosylation specificity of Acremonium sp. α-rhamnosyl-β-glucosidase and its application to the synthesis of the new fluorogenic substrate 4-methylumbelliferyl-rutinoside.
PubMed:
Quercetin production from rutin by a thermostable β-rutinosidase from Pyrococcus furiosus.
PubMed:
Characteristic fragmentation patterns of trimethylsilyl and trimethylsilyl-oxime derivatives of plant disaccharides as obtained by gas chromatography coupled to ion-trap mass spectrometry.
PubMed:
Structure of flavonoids influences the degree inhibition of Benzo(a)pyrene - induced DNA damage and micronuclei in HepG2 cells.
PubMed:
α-Rhamnosyl-β-glucosidase-catalyzed reactions for analysis and biotransformations of plant-based foods.
PubMed:
Characterization of two distinct glycosyl hydrolase family 78 alpha-L-rhamnosidases from Pediococcus acidilactici.
PubMed:
Determination of free inositols and other low molecular weight carbohydrates in vegetables.
PubMed:
Acylated flavonol glycosides from the forage legume, Onobrychis viciifolia (sainfoin).
PubMed:
Hesperidin suppresses ovalbumin-induced airway inflammation in a mouse allergic asthma model.
PubMed:
Protective mechanism of quercetin and rutin on 2,2'-azobis(2-amidinopropane)dihydrochloride or Cu2+-induced oxidative stress in HepG2 cells.
PubMed:
Preparative separation of phenolic compounds from Halimodendron halodendron by high-speed counter-current chromatography.
PubMed:
Ingested quercetin but not rutin increases accumulation of hepatic beta-carotene in BALB/c mice.
PubMed:
Extracellular monoenzyme deglycosylation system of 7-O-linked flavonoid beta-rutinosides and its disaccharide transglycosylation activity from Stilbella fimetaria.
PubMed:
Two novel disaccharides, rutinose and methylrutinose, are involved in carbon metabolism in Datisca glomerata.
PubMed:
Degradation of rutin by Thermoactinomyces vulgaris and other thermophilic compost isolates.
PubMed:
Immobilization of flavonol 3-O-beta-heterodisaccharidase on porous glass and production of rutinose from rutin.
PubMed:
Substrate specificities of glycosidases from Aspergillus species pectinase preparations on elderberry anthocyanins.
PubMed:
Syntheses of R-beta-rutinosides by rutin-degrading reaction.
PubMed:
In vitro biological evaluation of novel 7-O-dialkylaminoalkyl cytotoxic pectolinarigenin derivatives against a panel of human cancer cell lines.
PubMed:
Characteristic fragmentation patterns of the trimethylsilyl and trimethylsilyl-oxime derivatives of various saccharides as obtained by gas chromatography coupled to ion-trap mass spectrometry.
PubMed:
A novel antioxidant phenyl disaccharide from Populus tremula knotwood.
PubMed:
Characterization and identification of isomeric flavonoid O-diglycosides from genus Citrus in negative electrospray ionization by ion trap mass spectrometry and time-of-flight mass spectrometry.
PubMed:
Differential effects of flavonoids on bovine kidney low molecular mass protein tyrosine phosphatase.
PubMed:
Fate of anthocyanins and antioxidant capacity in contents of the gastrointestinal tract of weanling pigs following black raspberry consumption.
PubMed:
[HPLC investigation of antioxidant components in Solidago herba].
PubMed:
Aglycones and sugar moieties alter anthocyanin absorption and metabolism after berry consumption in weanling pigs.
PubMed:
Potential antitumor agents: flavones and their derivatives from Linaria reflexa Desf.
PubMed:
Identification and characterization of anthocyanins by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry in common foods in the United States: vegetables, nuts, and grains.
PubMed:
Silver complexation and tandem mass spectrometry for differentiation of isomeric flavonoid diglycosides.
PubMed:
Threshold dissociation and molecular modeling of transition metal complexes of flavonoids.
PubMed:
Characterization of flavonoids by aluminum complexation and collisionally activated dissociation.
PubMed:
Identification and quantification of phenolic compounds in berries of Fragaria and Rubus species (family Rosaceae).
PubMed:
Anti-inflammatory effect of heme oxygenase 1: glycosylation and nitric oxide inhibition in macrophages.
PubMed:
Structure-activity relationship (SAR) between some natural flavonoids and ocular blood flow in the rabbit.
PubMed:
Protein-lipid interactions during liposome oxidation with added anthocyanin and other phenolic compounds.
PubMed:
The inhibitory effects of 12 medicinal plants and their component compounds on lipid peroxidation.
PubMed:
Rutinoside at C7 attenuates the apoptosis-inducing activity of flavonoids.
PubMed:
Study on the inhibitory effects of Korean medicinal plants and their main compounds on the 1,1-diphenyl-2-picrylhydrazyl radical.
PubMed:
Purification and characterization of a flavonol 3-O-beta-heterodisaccharidase from the dried herb of Fagopyrum esculentum Moench.
PubMed:
Differential apoptosis-inducing effect of quercetin and its glycosides in human promyeloleukemic HL-60 cells by alternative activation of the caspase 3 cascade.
PubMed:
t-BOOH-induced oxidative damage in sickle red blood cells and the role of flavonoids.
PubMed:
Anti-Sindbis activity of flavanones hesperetin and naringenin.
PubMed:
Structural characterization of flavonoid glycosides by collisionally activated dissociation of metal complexes.
PubMed:
In vitro inhibitory effect of some flavonoids on rotavirus infectivity.
PubMed:
A beta-rutinosidase from Penicillium rugulosum IFO 7242 that is a peculiar flavonoid glycosidase.
PubMed:
The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man.
PubMed:
Electrochemistry of catechol-containing flavonoids.
PubMed:
[Structure of swertiamacroside from Swertia macrosperma C.B. Clark].
PubMed:
Isolation and characterization of esters of indole-3-acetic acid from the liquid endosperm of the horse chestnut (Aesculus species).
PubMed:
Interference of some flavonoids and non-steroidal anti-inflammatory drugs with oxidative metabolism of arachidonic acid by human platelets and neutrophils.
PubMed:
[alpha-L-Rhamnosidase from Fagopyrum esculentum: purification and some properties (author's transl)].