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Record Information
Version3.6
Creation Date2008-08-13 15:55:03 UTC
Update Date2013-02-09 00:15:26 UTC
HMDB IDHMDB06857
Secondary Accession NumbersNone
Metabolite Identification
Common NameDextrin
DescriptionDextrins are a group of low-molecular-weight carbohydrates produced by the hydrolysis of starch. Dextrins are mixtures of linear α-(1,4)-linked D-glucose polymers starting with an α-(1,6) bond. Because branched amylopectin and glycogen also contain α-(1,6) bonds, which α-amylase cannot hydrolyze in humans, the digest resulting from this action contains a mixture of dextrins. They have the same general formula as carbohydrates but are of shorter chain length. Industrial production is, in general, performed by acidic hydrolysis of potato starch. Dextrins are water-soluble, white to slightly yellow solids that are optically active. Under analysis, dextrins can be detected with iodine solution, giving a red coloration. The cyclical dextrins are known as cyclodextrins. They are formed by enzymatic degradation of starch by certain bacteria, for example, Bacillus macerans. Cyclodextrins have toroidal structures formed by 6-8 glucose residues. Dextrins find widespread use in industry, due to their non-toxicity and their low price. They are used as water-soluble glues, as thickening agents in food processing, and as binding agent in pharmaceuticals. In pyrotechnics, they are added to fire formulas, allowing them to solidify as pellets or "stars." Cyclodextrins find additional use in analytical chemistry as a matrix for the separation of hydrophobic substances, and as excipients in pharmaceutical formulations. Not all forms of dextrin are digestible, and indigestible dextrin is sometimes used in fiber supplements. For example, maltodextrin either can be moderately sweet or have hardly any flavor at all. Maltodextrin is a polysaccharide that is used as a food additive. It is produced from starch and is usually found as a creamy-white hygroscopic powder. Maltodextrin is easily digestible, being absorbed as rapidly as glucose. The CAS registry number of maltodextrin is 9050-36-6. Maltodextrin can be derived from any starch. In the US, this starch is usually rice, corn or potato; elsewhere, such as in Europe, it is commonly wheat. This is important for coeliacs, since the wheat-derived maltodextrin can contain traces of gluten. There have been recent reports of coeliac reaction to maltodextrin in the United States. This might be a consequence of the shift of corn to ethanol production and its replacement with wheat in the formulation. The fast food chain, Wendy's, footnotes maltodextrin in its list of gluten-free foods [1], which may be a sign of their receiving reports of this. Foods containing maltodextrin may contain traces of amino acids, including glutamic acid as a manufacturing by-product. The amino acid traces would be too small to have any dietary significance.(Wikipedia).
Structure
Thumb
Synonyms
  1. British gum
  2. Caloreen
  3. Corn dextrin
  4. Crystal gum
  5. Dextrid
  6. Dextrin
  7. Dextrina Bianca
  8. Dextrine
  9. Dextrins
  10. Fortodex
Chemical FormulaC18H32O16
Average Molecular Weight504.4371
Monoisotopic Molecular Weight504.169034976
IUPAC Name(3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional IUPAC Namemaltodextrin
CAS Registry Number9004-53-9
SMILES
OC[C@H]1OC(O[C@H]2[C@H](O)[C@@H](O)C(O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16+,17?,18?/m1/s1
InChI KeyFYGDTMLNYKFZSV-MRCIVHHJSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassTrisaccharides
Sub ClassTrihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • a linear malto-oligosaccharide(Cyc)
  • a short glucan(Cyc)
  • a trisaccharide(Cyc)
Substituents
  • 1,2 Diol
  • Acetal
  • Glycosyl Compound
  • Hemiacetal
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentTrihexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility554 g/LALOGPS
logP-2.7ALOGPS
logP-6.5ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)11.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area268.68ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.75ChemAxon
Polarizability46.19ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Starch and Sucrose MetabolismSMP00058map00500
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012148
KNApSAcK IDNot Available
Chemspider ID56445
KEGG Compound IDC00721
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06857
Metagene LinkHMDB06857
METLIN IDNot Available
PubChem Compound62698
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name:
SI
Uniprot ID:
P14410
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
Multifunctional enzyme acting as 1,4-alpha-D-glucan:1,4-alpha-D-glucan 4-alpha-D-glycosyltransferase and amylo-1,6-glucosidase in glycogen degradation.
Gene Name:
AGL
Uniprot ID:
P35573
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
AMY1A
Uniprot ID:
P04745
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
AMY2A
Uniprot ID:
P04746
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
AMY2B
Uniprot ID:
P19961
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing.
Gene Name:
MGAM
Uniprot ID:
O43451
Molecular weight:
Not Available
General function:
Involved in lysozyme activity
Specific function:
Hydrolysis of (1->4)-beta-linkages between N- acetylmuramic acid and N-acetyl-D-glucosamine residues in a peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrins
Gene Name:
LYZL1
Uniprot ID:
Q6UWQ5
Molecular weight:
16654.0