Record Information
Version1.0
Creation date2015-10-09 22:28:40 UTC
Update date2017-01-19 02:36:13 UTC
FoodComEx IDPC000125
FoodDB RecordFDB001204
Chemical Information
NameMelibiose
DescriptionIsolated 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). Melibiose is found in many foods, some of which are sesbania flower, mugwort, olive, and jerusalem artichoke.
CAS Number585-99-9
Structure
Thumb
Synonyms
SynonymSource
(Gal)1 (glc)1ChEBI
6-(a-D-galactosido)-D-glucosebiospider
6-(a-delta-galactosido)-delta-glucosebiospider
6-(D-galactosido)-D-glucosebiospider
6-(D-galactosido)-delta-glucosebiospider
6-O-(a-D-Galactopyranosyl)-D-glucopyranoseGenerator
6-O-(alpha-D-Galactopyranosyl)-D-glucopyranosebiospider
6-O-(α-D-galactopyranosyl)-D-glucopyranoseGenerator
6-O-a-D-Galactopyranosyl-D-glucopyranoseGenerator
6-O-a-D-Galactopyranosyl-D-glucoseHMDB
6-O-alpha-D-Galactopyranosyl-D-glucopyranoseChEBI
6-O-alpha-D-galactopyranosyl-D-Glucosebiospider
6-O-alpha-delta-galactopyranosyl-delta-Glucosebiospider
6-O-Hexopyranosylhexosebiospider
6-O-α-D-galactopyranosyl-D-glucopyranoseGenerator
a-D-Gal-(1->6)-D-glcGenerator
a-D-Galactosyl-(1->6)-D-glucoseGenerator
a-D-Galp-(1->6)-D-glcpGenerator
alpha-D-Gal-(1->6)-D-glcChEBI
alpha-D-Galactosyl-(1->6)-D-glucoseChEBI
alpha-D-Galp-(1->6)-D-glcpChEBI
Alpha-d-melibiosebiospider
Alpha-delta-melibiosebiospider
Alpha-melibiosebiospider
D-(+)-melibiosebiospider
D-Gal-alpha1->6D-Glucosebiospider
D-Glucose, 6-O-α-D-galactopyranosyl-biospider
D-melibiosebiospider
Delta-(+)-melibiosebiospider
Delta-melibiosebiospider
Gal-a(1,6)glcGenerator
Gal-alpha(1,6)glcChEBI
Gal-α(1,6)glcGenerator
Melibiose (van)biospider
Melibiose, 8CIdb_source
Mellibiosebiospider
α-D-gal-(1->6)-D-glcGenerator
α-D-galactosyl-(1->6)-D-glucoseGenerator
α-D-galp-(1->6)-D-glcpGenerator
Chemical FormulaNot Available
IUPAC nameNot Available
InChI IdentifierInChI=1S/3C12H22O11/c13-1-4-5(15)6(16)9(19)12(22-4)21-2-3(14)10-7(17)8(18)11(20)23-10;13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4;13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h2*3-20H,1-2H2;1,4-12,14-21H,2-3H2
InChI KeyYFSMDFMEDLKMOS-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OCC(O)C(O)C(O)C(O)C=O)C(O)C(O)C1O.OCC1OC(OCC(O)C2OC(O)C(O)C2O)C(O)C(O)C1O.OCC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight1026.8894
Monoisotopic Molecular Weight1026.348634638
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water Solubility1000 mg/mLMERCK INDEX (1996)
Melting PointMp 179-181° (monohydrate)DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci C810
Glentham GC9604
MetaSci HMDB0000048
Pfanstiehl Laboratories HMDB0000048