AFCDB: D-Maltose (FDB112196)

Record Information

Version

1.0

Creation date

2020-04-20 17:41:16 UTC

Update date

2020-09-17 15:42:25 UTC

Primary ID

FDB112196

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

D-Maltose

Description

D-Maltose, also known as malt sugar, maltobiose or alpha-malt sugar, is a disaccharide consisting of two glucose subunits joined via an alpha-1-4 bond. Carbohydrates are generally divided into different categories based on the number of sugar subunits; monosaccharides (1 sugar subunit), disaccharides (2 sugar subunits), oligosaccharides (3 or more sugar subunits) and polysaccharides (hundreds to thousands of subunits, including starch). Maltose is a common byproduct of starch. When beta-amylase breaks down starch, it removes two glucose units at a time, thereby producing maltose. Maltose can be broken down to glucose by the maltase enzyme, which catalyses the hydrolysis of the glycosidic bond. D-Maltose exists in all living species, ranging from bacteria to humans. Maltose was 'discovered' by Augustin-Pierre Dubrunfaut, although this discovery was not widely accepted until it was confirmed in 1872 by Irish chemist and brewer Cornelius O'Sullivan. Its name comes from malt, combined with the suffix '-ose' which is used in naming all sugars. Like glucose, maltose is a reducing sugar, because the ring of one of the two glucose units can open to present a free aldehyde group. Maltose, when placed in aqueous solution, exhibits mutarotation. This is because the α and β isomers that are formed by the different conformations of the anomeric carbon have different specific rotations. In aqueous solutions, these two forms are in equilibrium. Maltose has a sweet taste, but is only about 30-60% as sweet as sucrose. Within humans, D-maltose participates in a number of enzymatic reactions. In particular, D-maltose can be converted into Alpha-D-glucose; which is mediated by intestinal maltase-glucoamylase. In addition, D-maltose can be converted into Alpha-D-glucose through its interaction with the enzyme glycogen debranching enzyme. In humans, D-maltose is involved in the metabolic disorder called the sucrase-isomaltase deficiency. Outside of the human body, D-maltose is found in high concentrations a variety of foods such as fruit gums, marshmallows, and oriental wheats. It is found in lower concentrations in bread, bagels, breakfast cereals, crackers, cornmeal, wheat, barley, candies, honey, molasses, beer and wines. Maltose is found mainly in grains and cereals. Wheat, corn, barley and rye all contain varying amounts of maltose. For some foods, cooking can increase the maltose content. For example, raw sweet potatoes don't have any maltose, but cooked sweet potatoes contain maltose at varying amounts depending on the type of sweet potato. Maltose is a component of malt, a substance which is obtained in the process of allowing grain to soften in water and germinate. Maltose is also found in partially hydrolysed starch products like maltodextrin, corn syrup and acid-thinned starch.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	586 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.7	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	11.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	31.43 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H22O11

IUPAC name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol

InChI Identifier

InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9-,10-,11+,12-/m1/s1

InChI Key

GUBGYTABKSRVRQ-DKBJLJRDSA-N

Isomeric SMILES

OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O

Average Molecular Weight

342.2965

Monoisotopic Molecular Weight

342.116211546

Classification

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

alpha-D-glucosyl-(1->4)-D-mannopyranose (CHEBI:47937 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	D-Maltose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03e9-4897000000-332d470623cd7f1e1ced	Spectrum
Predicted GC-MS	D-Maltose, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-3421129000-03a98898fd3278f95502	Spectrum
Predicted GC-MS	D-Maltose, TBDMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TBDMS_3_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TBDMS_4_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TBDMS_4_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TBDMS_4_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TBDMS_4_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TBDMS_4_20, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TBDMS_4_32, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TBDMS_4_33, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, "D-Maltose,3TBDMS,#3" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Maltose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01ox-0149000000-74748828832d87932342	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-008c-2950000000-4ebee22b86c2cc9ee3ab	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kg-9710000000-041dbc580f99b8881518	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03gl-0907000000-a1de7813fbe8b5258c10	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0900000000-79cc5059a3f338e8c1dd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3900000000-851d0bc84d91b6e09579	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0749000000-af1d18f2bc3ab8e02883	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0200-2902000000-67218697344afb9e70fa	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01td-4900000000-40aa2d8125769803cfbb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0109000000-9d0f9a68a67bafd734ab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01rw-3898000000-7f495a1bcfdbed6466c4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ti-9210000000-b8a83657f0266d372bee	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000x-1069000000-9cd867711bca0eecf935	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9365000000-65403961bfb5e35eaa0d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9200000000-0de9785c1c5df1430dd2	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

D-Maltose (FDB112196)

Structure for FDB112196 (D-Maltose)