You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:01 UTC
Update Date2018-05-20 09:44:53 UTC
HMDB IDHMDB0031554
Secondary Accession Numbers
  • HMDB31554
Metabolite Identification
Common NameSucralose
DescriptionSucralose is a noncalorific sweetener with good taste properties One report suggests sucralose is a possible trigger for some migraine patients. Another study published in the Journal of Mutation Research linked doses of sucralose equivalent to 11,450 packets per day in a person to DNA damage in mice. Results from over 100 animal and clinical studies in the FDA approval process unanimously indicated a lack of risk associated with sucralose intake. However, some adverse effects were seen at doses that significantly exceeded the estimated daily intake (EDI), which is 1.1 mg/kg/day. When the EDI is compared to the intake at which adverse effects are seen, known as the highest no adverse effects limit (HNEL), at 1500 mg/kg/day, there is a large margin of safety. The bulk of sucralose ingested is not absorbed by the gastrointestinal (GI) tract and is directly excreted in the feces, while 11-27% of it is absorbed. The amount that is absorbed from the GI tract is largely removed from the blood stream by the kidneys and eliminated in the urine with 20-30% of the absorbed sucralose being metabolized. Sucralose belongs to a class of compounds known as organochlorides (or chlorocarbons). Some organochlorides, particularly those that accumulate in fatty tissues, are toxic to plants or animals, including humans. Sucralose, however, is not known to be toxic in small quantities and is extremely insoluble in fat; it cannot accumulate in fat like chlorinated hydrocarbons. In addition, sucralose does not break down or dechlorinate. Sucralose can be found in more than 4,500 food and beverage products. It is used because it is a no-calorie sweetener, does not promote dental caries, and is safe for consumption by diabetics. Sucralose is used as a replacement for, or in combination with, other artificial or natural sweeteners such as aspartame, acesulfame potassium or high-fructose corn syrup. Sucralose is used in products such as candy, breakfast bars and soft drinks. It is also used in canned fruits wherein water and sucralose take the place of much higher calorie corn syrup based additives. Sucralose mixed with maltodextrin or dextrose (both made from corn) as bulking agents is sold internationally by McNeil Nutritionals under the Splenda brand name. In the United States and Canada, this blend is increasingly found in restaurants, including McDonald's, Tim Hortons and Starbucks, in yellow packets, in contrast to the blue packets commonly used by aspartame and the pink packets used by those containing saccharin sweeteners; though in Canada yellow packets are also associated with the SugarTwin brand of cyclamate sweetener. Sucralose is a highly heat-stable artificial sweetener, allowing it to be used in many recipes with little or no sugar. Sucralose is available in a granulated form that allows for same-volume substitution with sugar. This mix of granulated sucralose includes fillers, all of which rapidly dissolve in liquids.[citation needed] Unlike sucrose which dissolves to a clear state, sucralose suspension in clear liquids such as water results in a cloudy state. For example, gelatin and fruit preserves made with sucrose have a satiny, near jewel-like appearance, whereas the same products made with sucralose (whether cooked or not) appear translucent and marginally glistening.[citation needed] While the granulated sucralose provides apparent volume-for-volume sweetness, the texture in baked products may be noticeably different. Sucralose is non-hygroscopic, meaning it does not attract moisture, which can lead to baked goods that are noticeably drier and manifesting a less dense texture than baked products made with sucrose. Unlike sucrose which melts when baked at high temperatures, sucralose maintains its granular structure when subjected to dry, high heat (e.g., in a 350 ¬?F (177 ¬?C) oven). Thus, in some baking recipes, such as burnt cream, which require sugar sprinkled on top to partially or fully melt and crystallize, substituting sucralose will not result in the same surface texture, crispness, or crystalline structure. Sucralose is a zero-calorie sugar substitute artificial sweetener. In the European Union, it is also known under the E number (additive code) E955. Sucralose is approximately 600 times as sweet as sucrose (table sugar), twice as sweet as saccharin, and 3.3 times as sweet as aspartame. Unlike aspartame, it is stable under heat and over a broad range of pH conditions. Therefore, it can be used in baking or in products that require a longer shelf life. The commercial success of sucralose-based products stems from its favorable comparison to other low-calorie sweeteners in terms of taste, stability, and safety
Structure
Thumb
Synonyms
ValueSource
1',4,6'-TrichlorogalactosucroseHMDB
1,6-dichloro-1,6-Dideoxy-b-D-fructofuranosyl 4-chloro-4-deoxy-a-D-galactopyranoside, 9ciHMDB
4,1',6'-trichloro-4,1',6'-Trideoxy-galacto-sucroseHMDB
4,1',6'-trichloro-4,1',6'-TrideoxygalactosucroseHMDB
SplendaHMDB
SucraloseHMDB
trichlorogalacto-SucroseHMDB
TrichlorogalactosucroseHMDB
TrichlorosucroseHMDB
Chemical FormulaC12H19Cl3O8
Average Molecular Weight397.633
Monoisotopic Molecular Weight396.014550705
IUPAC Name2-{[2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-chloro-6-(hydroxymethyl)oxane-3,4-diol
Traditional Namesucralose
CAS Registry Number56038-13-2
SMILES
OCC1OC(OC2(CCl)OC(CCl)C(O)C2O)C(O)C(O)C1Cl
InChI Identifier
InChI=1S/C12H19Cl3O8/c13-1-4-7(17)10(20)12(3-14,22-4)23-11-9(19)8(18)6(15)5(2-16)21-11/h4-11,16-20H,1-3H2
InChI KeyBAQAVOSOZGMPRM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentC-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Ketal
  • Oxane
  • Monosaccharide
  • Tetrahydrofuran
  • Secondary alcohol
  • Chlorohydrin
  • Halohydrin
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Primary alcohol
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.9 g/LALOGPS
logP-0.39ALOGPS
logP-0.47ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.84 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.93 m³·mol⁻¹ChemAxon
Polarizability35.27 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6529000000-71b0d3e6e99513964137View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00di-2202019000-ac57173953cc3ccddddfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0970000000-890d1664b7f0d2dc8e38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0910000000-97705d7fbd5efa1af93eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fs-3900000000-5ecc7edf6a58c1d57107View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ta-2952000000-f745d094097fdac7b629View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fs-0930000000-dfd66662140ae1064c80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-3910000000-af96e86d9a4682a3a9fdView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008166
KNApSAcK IDNot Available
Chemspider ID4243140
KEGG Compound IDC12285
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5066234
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .