Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H32O16 |
| Molecular Weight | 504.4371 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 14 / 14 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O
InChI
InChIKey=MUPFEKGTMRGPLJ-ZQSKZDJDSA-N
InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1
Raffinose is a dextrorotatory trisaccharide, occurring in cotton seed and in the molasses of beet root, composed of d-galactose, d-glucose, and d-fructose and formed by transfer of d-galactose from UDP-d-galactose to sucrose; many seeds are rich in raffinose. Raffinose can be hydrolyzed to sucrose and galactose by the enzyme α-galactosidase (α-GAL). Humans do not possess the α-GAL enzyme in their small intestine to break down the trisaccharide. Thus bigger amounts of raffinose reach the large intestine, where bacteria of the gut flora perform the break down and produce gases. This may cause flatulence. Due to its indestigibility, raffinose is sometimes used in foods to reduce calories. Legume seeds (peas, beans, lentils) contain 5 to 15 % raffinose in their dry weight. During the production of beet sugar, major amounts of raffinose accumulate in the molasses, which can be used to produce some kinds of brown sugars. Technically, raffinose can be used as a antifreezing agent (freezing medical preparates, cryopreservation). Dietary raffinose has being shown to suppress serum immunoglobulin E response through suppression of Th2-type immune response against oral antigen in the lymphoid organs located in or near the intestine. 4.5% raffinose is an effective osmotic agent. Raffinose has being used experimentally as an osmotic agent for peritoneal dialysis. Raffinose is used in reproductive medicine. The addition of raffinose to media containing glucose improved motility of sperm stored at 3 degrees C for 6 h.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Advantages of Celsior solution in graft preservation from non-heart-beating donors in a canine liver transplantation model. | 2002-02 |
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| [Effect of preservation of the kidney on the long-term function following autotransplantation]. | 2002-01-25 |
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| Pretransplant rinse of hearts preserved with colloid-free UW solution and more effective heart preservation: studies in a rat abdominal heart transplant model. | 2002-01-15 |
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| Chain Elongation of raffinose in pea seeds. Isolation, characterization, and molecular cloning of mutifunctional enzyme catalyzing the synthesis of stachyose and verbascose. | 2002-01-04 |
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| Improved right heart function after myocardial preservation with 2,3-butanedione 2-monoxime in a porcine model of allogenic heart transplantation. | 2002-01 |
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| Aerobic ischemia by venous systemic O(2) persufflation (VSOP) during cold storage of predamaged livers: molecular impact and physiologic benefit. | 2001-12-26 |
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| Potential of hemoglobin-based oxygen carriers in trauma patients. | 2001-12 |
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| Efficient protoplast regeneration for some homofermentative lactobacilli and pediococci. | 2001-12 |
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| University of Wisconsin solution increases hyperpolarizing mechanisms in response to bradykinin. | 2001-12 |
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| Analysis of the raffinose family oligosaccharide pathway in pea seeds with contrasting carbohydrate composition. | 2001-12 |
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| Effect of perfusion during ischemia on skeletal muscle. | 2001-12 |
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| Purification and characterization of three galactose specific lectins from mulberry seeds (Morus sp.). | 2001-12 |
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| Evidence for intraprotein charge transfer during the transport activity of the melibiose permease from Escherichia coli. | 2001-11-13 |
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| The effects of hemodilution with Hemolink upon hemodynamics and blood flow distribution in anesthetized dogs. | 2001-11 |
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| Ranking of gas-phase acidities and chloride affinities of monosaccharides and linkage specificity in collision-induced decompositions of negative ion electrospray-generated chloride adducts of oligosaccharides. | 2001-11 |
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| Cannulation of the aorta in organ donors with infrarenal aortic pathologies. | 2001-11 |
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| Evaluation of a biochemical test scheme for identifying clinical isolates of Enterococcus faecalis and Enterococcus faecium. | 2001-11 |
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| Desiccation tolerance of protoplasts isolated from pea embryos. | 2001-11 |
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| Kidney preservation with university of Wisconsin and Celsior solution: a prospective multicenter randomized study. | 2001-10-15 |
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| Water sorption/desorption--near IR and calorimetric study of crystalline and amorphous raffinose. | 2001-10-04 |
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| Expression and activity of the Hxt7 high-affinity hexose transporter of Saccharomyces cerevisiae. | 2001-09-30 |
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| Apoptosis versus necrosis during cold storage and rewarming of human renal proximal tubular cells. | 2001-09-15 |
|
| Aft2p, a novel iron-regulated transcription activator that modulates, with Aft1p, intracellular iron use and resistance to oxidative stress in yeast. | 2001-09-07 |
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| [The domestic processing of the common bean resulted in a reduction in the phytates and tannins antinutritional factors, in the starch content and in the raffinose, stachiose and verbascose flatulence factors]. | 2001-09 |
|
| Characteristics of an alpha-galactosidase associated with grape flesh. | 2001-09 |
|
| Characterization of alpha-galactosidases from germinating soybean seed and their use for hydrolysis of oligosaccharides. | 2001-09 |
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| Cytokine up-regulation in ischaemic/reperfused lungs perfused with University of Wisconsin solution and normal saline. | 2001-09 |
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| Expression of intercellular adhesion molecule-1 in the cortex of preserved rat kidneys. | 2001-09 |
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| To be or not to be: a question of B-Raf? | 2001-09 |
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| Preservation of metabolic reserves and function after storage of myocytes in hypothermic UW solution. | 2001-09 |
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| Hyperosmolality activates Akt and regulates apoptosis in renal tubular cells. | 2001-08 |
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| [Preservation of hepatocytes in UW and HTK solutions with added fluorocarbons]. | 2001-07-24 |
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| Effects of a p38 mitogen-activated protein kinase inhibitor as an additive to university of wisconsin solution on reperfusion injury in liver transplantation. | 2001-07-15 |
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| Oxygen carriers ("blood substitutes"). | 2001-07 |
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| The CF salt controversy: in vivo observations and therapeutic approaches. | 2001-07 |
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| Fast, nondestructive measurement of frost hardiness in conifer seedlings by VIS+NIR spectroscopy. | 2001-07 |
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| Fibrinolytic preflush upon liver retrieval from non-heart beating donors to enhance postpreservation viability and energetic recovery upon reperfusion. | 2001-06-27 |
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| Comparative evaluation of Celsior solution versus Viaspan in a pig liver transplantation model. | 2001-06-27 |
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| Hepatic uptake of solutes from the preservation solution during hypothermic storage: a (1)H NMR study in rat liver. | 2001-06 |
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| Effect of ursodeoxycholate in University of Wisconsin solution on long term preservation of rat livers. | 2001-06 |
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| Respiratory activity of isolated rat hepatocytes following cold storage and subsequent rewarming: a comparison of sucrose-based and University of Wisconsin solutions. | 2001-05 |
|
| Soy molasses as fermentation substrate for production of butanol using Clostridium beijerinckii BA101. | 2001-05 |
|
| Effect of sucrose/raffinose mass ratios on the stability of co-lyophilized protein during storage above the Tg. | 2001-04 |
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| Three-dimensional morphological analysis of antigen-antibody reaction in hepatic sinusoids preserved in hypothermic UW solution. | 2001-03 |
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| Vitrification of mouse oocytes in ethylene glycol-raffinose solution: effects of preexposure to ethylene glycol or raffinose on oocyte viability. | 2001-03 |
|
| In vitro viability, mitogenicity and clonogenic capacities of periodontal ligament fibroblasts after storage in four media supplemented with growth factors. | 2001-02 |
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| O-raffinose-polymerised haemoglobin. A biochemical and pharmacological profile of an oxygen carrier. | 2001-01 |
|
| Muscular expressions: profiling genes in complex tissues. | 2001 |
|
| Swelling of capillary endothelial cells and cardiomyocytes in the ischaemic myocardium of artificially arrested canine hearts. | 2001 |
|
| Optimization of alpha-galactosidase production in Streptomyces erythrus. | 2001 |
Patents
Sample Use Guides
Mice: feeding a diet supplemented with 50 g raffinose/kg to BALB/c mice significantly (P<0.05) increased interleukin (IL) 12 secretion from isolated Peyer's patch (PP) cells in vitro compared with feeding control diet.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Raffinose resulted in higher survival rates of frozen-thawed mouse spermatozoa, especially at a concentration of around 0.35 mol/kg H(2)O (0.381-0.412 Osm/kg). https://www.ncbi.nlm.nih.gov/pubmed/10860623
In stock solution with supplements of 15 mM Mg or a combination of 5 mM Mg and 10 mM raffinose or sucrose, a significantly higher number of oocytes developed into blastocysts with a large number of cells in each blastocyst, and a significantly higher number of living granulosa cells were obtained as compared with stock solutions without any supplements.
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NCI_THESAURUS |
C714
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m9483
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RAFFINOSE
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SUBSTANCE RECORD
