Record Information
Version1.0
Creation date2010-04-08 22:04:50 UTC
Update date2018-05-28 22:37:35 UTC
Primary IDFDB001109
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Tagatose
DescriptionGRAS status for use as a sweetener, humectant, texturiser or stabiliser in food, especies low calorie products D-Tagatose, a rare natural hexoketose, is an isomer of d-galactose. D-Tagatose occurs naturally in Sterculia setigera gum, and it is also found in small quantities in various foods such as sterilized and powdered cow's milk, hot cocoa, and a variety of cheeses, yogurts, and other dairy products. It can be synthesized from D-galactose by isomerization under alkaline conditions in the presence of calcium. D-Tagatose have numerous health benefits, including promotion of weight loss, no glycemic effect, anti-plaque, non-cariogenic, anti-halitosis, prebiotic, and anti-biofilm properties, organ transplants, enhancement of flavor, improvement of pregnancy and fetal development, treatment of obesity, and reduction in symptoms associated with type 2 diabetes, hyperglycemia, anemia, and hemophilia. (PMID: 17492284); Oral tagatose significantly blunts the rise in plasma glucose seen after oral glucose in patients with diabetes mellitus in a dose-dependent manner without significantly affecting insulin levels. The minimal elevation of plasma tagatose levels in normal patients and the adverse gastrointestinal effects seen following larger doses of tagatose support poor absorption of this hexose and suggest that tagatose may act by attenuating glucose absorption in the intestine.; Tagatose is a functional sweetener. It is a naturally occurring monosaccharide, specifically a hexose. It is often found in dairy products, and is very similar in texture to sucrose (table sugar) and is 92% as sweet, but with only 38% of the calories.
CAS Number87-81-0
Structure
Thumb
Synonyms
SynonymSource
Lyxo-hexuloseChEBI
Tagatose, (beta-D)-isomerMeSH
Tagatose, (DL)-isomerMeSH
TagatoseMeSH
Tagatose, (alpha-D)-isomerMeSH
Tagatose, (D)-isomerMeSH
(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-onebiospider
D-lyxo-2-Hexulosebiospider
D-lyxo-hex-2-ulosebiospider
D-tagbiospider
D-tagatosebiospider
DL-tagatosebiospider
Keto-d-tagatosebiospider
lyxo-2-Hexulosebiospider
TAGbiospider
Tagatose, d-biospider
Predicted Properties
PropertyValueSource
logP-2.8ChemAxon
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.36 m³·mol⁻¹ChemAxon
Polarizability16.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H36O18
IUPAC name(3S,4S,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
InChI IdentifierInChI=1S/3C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6;7-1-3-4(9)5(10)6(11,2-8)12-3;7-1-3(9)5(11)6(12)4(10)2-8/h2*3-5,7-11H,1-2H2;3,5-9,11-12H,1-2H2
InChI KeyJCOXAIPZGMCTBN-UHFFFAOYSA-N
Isomeric SMILESOCC(O)C(O)C(O)C(=O)CO.OCC1OC(O)(CO)C(O)C1O.OCC1(O)OCC(O)C(O)C1O
Average Molecular Weight540.4676
Monoisotopic Molecular Weight540.190164348
Classification
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.00%; H 6.71%; O 53.28%DFC
Melting PointMp 134-135°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-3.202
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -5 (c, 1.0 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID83142
ChEMBL IDNot Available
KEGG Compound IDC00795
Pubchem Compound ID92092
Pubchem Substance IDNot Available
ChEBI ID16443
Phenol-Explorer IDNot Available
DrugBank IDDB04936
HMDB IDHMDB03418
CRC / DFC (Dictionary of Food Compounds) IDBTH92-X:BTH96-B
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36022
KNApSAcK IDNot Available
HET IDTAG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTagatose
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference