O-alpha-D-Glucopyranosyl-(1->4)-O-alpha-D-glucopyranosyl-(1->4)-D-glucopyranose
Basic information
- CAS
1109-28-0- Standard SMILES
OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O- InChIKey
FYGDTMLNYKFZSV-DZOUCCHMSA-N- Molecular formula
- C18H32O16
- Average molar mass
- 504.4 g/mol
- Monoisotopic mass
- 504.16903493
Overview
Alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-Glcp is a maltotriose trisaccharide in which the glucose residue at the reducing end is in the pyranose form. It is a glucotriose and a maltotriose trisaccharide.
Names & identifiers
- Preferred name
- O-alpha-D-Glucopyranosyl-(1->4)-O-alpha-D-glucopyranosyl-(1->4)-D-glucopyranose
- IUPAC
- (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
- English name
- Maltotriose
- Molecular formula
- C18H32O16
- Molecular weight
- 504.44
Names & synonyms
113158-51-3DTXSID801157137GlyTouCan:G33575ECRefChem:1048470DTXCID701588636G33575ECO-alpha-D-Glucopyranosyl-(1->4)-O-alpha-D-glucopyranosyl-(1->4)-D-glucopyranoseCHEBI:140999alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-GlcpOM06486O-alpha-D-Glucopyranosyl-(1-->4)-O-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranoseMaltotriose - Technical
Show more names
MaltotriseTRIOMALTOSEAMYLOTRIOSED-MALTOTRIOSEO-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-O-...D-Glucose, O-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-yyqhj112NSC 170180Malt triose
n+2 maltodextrinMaltooligosaccharidemaltodextrin(n-2)a-1,4-glucotrioseGlucose - Impurity Cdelta-(+)-MaltotrioseMaltotriose - UltrapureEpitope ID:857742
Properties
Computed structural properties
- XLogP
- -6.9
- Topological polar surface area
- 269 Ų
- Hydrogen bond donors
- 11
- Hydrogen bond acceptors
- 16
- Rotatable bonds
- 7
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 641
Experimental & physicochemical properties
Physical DescriptionSolid
Collision Cross Section
212.7 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
212.54 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
Physicochemical properties
- Melting point
- 132 · 132-135 °C
- Boiling point
- 513.84 °C · 513.84°C (rough estimate)
- Density
- 1.4403 · 1.4403 (rough estimate)
- refractive index
- 1.676 · 1.6760 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL, clear, colorless
- form
- Powder
- pka
- 12.39 · 12.39±0.20(Predicted)
- color
- White to Off-white
- optical activity
- 160 · +160
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29400090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysGalactose Metabolism
Applications
UsesA trisaccharide resulting from the digestion of Amalose by α-Amalase.
Usesdisplays potent and selective in vitro anti-human immunodeficiency virus type 1 activity. Prepared by modification of lysine e-amino groups
UsesMaltotriose is a matrose regulon inducer in Escherichia coli. Maltotriose has been used in a study to investigate the influence of fourth generation poly(propyleneimine) dendrimers on blood cells.
Preparation methods
PreparationIn nature, maltose is mainly found in germinated grains, especially malt, hence its name. Under the action of amylase, starch undergoes hydrolysis to produce maltodextrin, which further undergoes hydrolysis to produce two glucose molecules. Maltodextrin is a series of low-molecular-weight sugars obtained from starch hydrolysis; it is a group of linear α(1-4)-linked D-glucose polymers. Industrial-grade maltodextrin is typically produced by the acidic hydrolysis of potato starch. Maltotriose is composed of α(1-4)-linked D-glucose monomers with a degree of polymerization of 3.
Additional notes
DefinitionChEBI: A maltotriose trisaccharide in which the glucose residue at the reducing end is in the aldehydo open-chain form.
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