Showing Compound Maltitoll (FDB020369)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:59 UTC

Update date

2015-10-09 22:32:19 UTC

Primary ID

FDB020369

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Maltitoll

Description

Permitted bulk sweetener for foods Commercially, maltitol is a disaccharide produced by Corn Products Specialty Ingredients (formerly SPI Polyols), Cargill, Roquette, and Towa, among other companies. Maltitol is made by hydrogenation of maltose obtained from starch. Its high sweetness allows it to be used without being mixed with other sweeteners, and exhibits negligible cooling effect (positive heat of solution) in comparison with other sugar alcohols, and is very similar to the subtle cooling effect of sucrose. It is used especially in production of sweets: sugarless hard candies, chewing gum, chocolates, baked goods, and ice cream. The pharmaceutical industry uses maltitol as an excipient where it is utilised as a low-calorie sweetening agent. Its similarity to sucrose allows it to be used in syrups with the advantage that crystallization (which may cause bottle caps to stick) is less likely. Maltitol may also be used as a plasticiser in gelatine capsules, as an emollient, and as a humectant.; In countries such as Australia, Norway and New Zealand, it carries a mandatory warning such as "Excessive consumption may have a laxative effect." In the United States, it is a Generally recognized as safe (GRAS) substance, with a recommendation of a warning about its laxative potential when consumed at levels of 100 grams per day or more.; Maltitol is a sugar alcohol (a polyol) used as a sugar substitute. It has 75-90% of the sweetness of sucrose (table sugar) and nearly identical properties, except for browning. It is used to replace table sugar because it has fewer calories, does not promote tooth decay and has a somewhat lesser effect on blood glucose. Chemically, maltitol is also known as 4-O-?-glucopyranosyl-D-sorbitol. Commercially, it is known under trade names such as Maltisorb and Maltisweet.; Maltitol is a sugar alcohol (polyol) used as a sugar substitute. It has 90% the sweetness of sugar and nearly identical properties, except for browning. It is used to very easily replace sugar and has less food energy, does not promote tooth decay and has a somewhat lower blood sugar response. Unfortunately, maltitol is well known to cause gastric distress, particularly if consumed in great quantities. Chemically, maltitol is also known as 4-O-alpha-Glucopyranosyl-D-sorbitol. Commercially, it is known under trade names such as Maltisorb and Maltisweet. Due to its slow absorption, excessive consumption of Maltitol can have laxative effect and often can cause gas and/or bloating. Maltitol is particularly demonized regarding gastric side effects because it is so easy for food producers to use it in vast quantities (due to its amazingly sugar-like properties) so consumers often end up consuming far more than they could most other sugar alcohols. While this is a major problem with maltitol, many sugar alcohols are far more likely to cause gastric distress than maltitol when compared gram-for-gram. -- Wikipedia

CAS Number

585-88-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(2S,3R,4R,5R)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}hexane-1,2,3,5,6-pentol	ChEBI
4-O-alpha-D-Glucopyranosyl-D-glucitol	ChEBI
alpha-D-GLC-(1->4)-D-GLC-ol	ChEBI
alpha-D-GLCP-(1->4)-D-GLC-ol	ChEBI
alpha-D-Glucosyl-(1->4)-D-glucitol	ChEBI
D-Maltitol	ChEBI
WURCS=2.0/2,2,1/[H2122H][a2122h-1a_1-5]/1-2/a4-b1	ChEBI
4-O-a-D-Glucopyranosyl-D-glucitol	Generator
4-O-Α-D-glucopyranosyl-D-glucitol	Generator
a-D-GLC-(1->4)-D-GLC-ol	Generator
Α-D-GLC-(1->4)-D-GLC-ol	Generator
a-D-GLCP-(1->4)-D-GLC-ol	Generator
Α-D-GLCP-(1->4)-D-GLC-ol	Generator
a-D-Glucosyl-(1->4)-D-glucitol	Generator
Α-D-glucosyl-(1->4)-D-glucitol	Generator
4-O-alpha-delta-Glucopyranosyl-delta-glucitol	HMDB
Amalti syrup	HMDB
Amalty MR 100	HMDB
D-4-O-alpha-D-Glucopyranosylglucitol	HMDB
delta-4-O-alpha-delta-Glucopyranosylglucitol	HMDB
delta-Maltitol	HMDB
Malbit	HMDB
Malti MR	HMDB
Maltisorb	HMDB
Maltit	HMDB
Maltitol	HMDB
4-O-α-D-glucopyranosyl-D-glucitol	Generator
a-D-Glc-(1->4)-D-glc-ol	Generator
a-D-Glcp-(1->4)-D-glc-ol	Generator
alpha-D-Glc-(1->4)-D-glc-ol	ChEBI
alpha-D-Glcp-(1->4)-D-glc-ol	ChEBI
D-Glucitol, 4-O-alpha-D-glucopyranosyl-	biospider
D-glucopyranosyl-d-glucitol	biospider
D-maltitol	biospider
Delta-maltitol	biospider
E965	db_source
Glucitol, 4-O-alpha-D-glucopyranosyl-, D-	biospider
α-D-glc-(1->4)-D-glc-ol	Generator
α-D-glcp-(1->4)-D-glc-ol	Generator
α-D-glucosyl-(1->4)-D-glucitol	Generator

Predicted Properties

Property	Value	Source
Water Solubility	377 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-5.5	ChemAxon
logS	0.04	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	200.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	70.82 m³·mol⁻¹	ChemAxon
Polarizability	31.84 Å³	ChemAxon
Number of Rings	1	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

C12H24O11

IUPAC name

(2S,3R,4R,5R)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexane-1,2,3,5,6-pentol

InChI Identifier

InChI=1S/C12H24O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4-21H,1-3H2

InChI Key

VQHSOMBJVWLPSR-UHFFFAOYSA-N

Isomeric SMILES

OCC(O)C(O)C(OC1OC(CO)C(O)C(O)C1O)C(O)CO

Average Molecular Weight

344.3124

Monoisotopic Molecular Weight

344.13186161

Classification

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Sugar alcohol
Oxane
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

alpha-D-glucoside (CHEBI:68428 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 41.86%; H 7.03%; O 51.11%	DFC
Melting Point	Mp 149-152°	DFC
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	[a]21D +107 (c, 10 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	, non-derivatized, GC-MS Spectrum	splash10-0uxs-0952000000-b7f978a79c1e8d933177	Spectrum
Predicted GC-MS	, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03fr-9235000000-4b74058303ecc8c4b855	Spectrum
Predicted GC-MS	, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00kr-6460219000-7d7a8a9d3b52128e18e4	Spectrum
Predicted GC-MS	, TBDMS_3_50, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_3_52, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_57, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_59, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_72, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_73, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_92, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_93, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_94, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_95, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_96, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_99, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_100, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_4_112, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, "Maltitol,3TBDMS,#50" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0h4x-8904000000-348f04d18d9ab4a54309	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-002f-1279000000-89dc38b09b82fe640e58	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-74f3005b7f662c942544	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1190000000-0c5fa032896efc821669	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0900000000-4c268ca31754a92aadb7	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9400000000-2cbc4727d166702a8dcf	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-067r-9000000000-090e156d979b54105c93	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-7d6f01e4ad770ea30d9e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-0095000000-646de9a950331e2820f5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-066r-0090000000-9f1519336d06d1d75d44	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000x-7694000000-a6af66a19f9a31c099b8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01u0-6931000000-12750896e8c10d0fcbc3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08fu-9700000000-156a606db9a67ec92434	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1129000000-2c95ce6a3d2cfa92e02a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9451000000-84f94577e31c56237ec2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-3350e8567bb71f6704d0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00o1-1908000000-27615cf754d66c0d1f21	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02u0-4901000000-b99d2d4b0115fe5091ae	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03xu-9810000000-6b21bfaddbf77f03a7b3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-054k-0209000000-281f58cfa23a6a50f0f7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9701000000-fd1529eaf380bfa9e951	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000w-9400000000-bea21dfb9029812122e5	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 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, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum