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Record Information
Version1.0
Created at2006-08-12 20:29:38 UTC
Updated at2021-06-29 00:47:47 UTC
NP-MRD IDNP0000789
Secondary Accession NumbersNone
Natural Product Identification
Common NameD-Tagatose
DescriptionD-Tagatose (CAS: 87-81-0), 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 has 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; obesity treatment; and reduction in symptoms associated with type 2 diabetes, hyperglycemia, anemia, and hemophilia (PMID: 17492284 ).
Structure
Thumb
Synonyms
ValueSource
D-Lyxo-2-hexuloseHMDB
D-Lyxo-hex-2-uloseHMDB
D-TagHMDB
Lyxo-2-hexuloseHMDB
Lyxo-hexuloseHMDB
TagatoseHMDB
Tagatose, (D)-isomerHMDB
Tagatose, (beta-D)-isomerHMDB
Tagatose, (alpha-D)-isomerHMDB
Tagatose, (DL)-isomerHMDB
D-TagatopyranoseHMDB
TagatopyranoseHMDB
beta-D-TagatopyranoseHMDB
beta-D-TagatoseHMDB
Β-D-tagatopyranoseHMDB
Β-D-tagatoseHMDB
b-D-TagatopyranoseHMDB
D-TagatoseHMDB
Chemical FormulaC6H12O6
Average Mass180.1560 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(2R,3S,4S,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Nameβ-D-tagatopyranose
CAS Registry Number87-81-0
SMILES
OC[C@@]1(O)OC[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5+,6-/m1/s1
InChI KeyLKDRXBCSQODPBY-DPYQTVNSSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Carica papaya L.Plant
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.202Not Available
Predicted Properties
PropertyValueSource
Water Solubility399 g/LALOGPS
logP-2.5ALOGPS
logP-2.8ChemAxon
logS0.82ALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003418
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001109
KNApSAcK IDC00019683
Chemspider ID10194220
KEGG Compound IDC00795
BioCyc IDD-tagatose
BiGG IDNot Available
Wikipedia LinkTagatose
METLIN IDNot Available
PubChem Compound14408225
PDB IDNot Available
ChEBI ID49092
Good Scents IDNot Available
References
General References
  1. Oh DK: Tagatose: properties, applications, and biotechnological processes. Appl Microbiol Biotechnol. 2007 Aug;76(1):1-8. Epub 2007 May 10. [PubMed:17492284 ]
  2. Donner TW, Wilber JF, Ostrowski D: D-tagatose, a novel hexose: acute effects on carbohydrate tolerance in subjects with and without type 2 diabetes. Diabetes Obes Metab. 1999 Sep;1(5):285-91. [PubMed:11225640 ]
  3. Dai Y, Zhang T, Jiang B, Mu W, Chen J, Hassanin HA: Dictyoglomus turgidum DSM 6724 alpha-Glucan Phosphorylase: Characterization and Its Application in Multi-enzyme Cascade Reaction for D-Tagatose Production. Appl Biochem Biotechnol. 2021 Aug 11. pii: 10.1007/s12010-021-03624-7. doi: 10.1007/s12010-021-03624-7. [PubMed:34379312 ]
  4. Suchy M, Charlton TA, Ben RN, Shuhendler AJ: Synthesis of natural/(13)C-enriched d-tagatose from natural/(13)C-enriched d-fructose. Carbohydr Res. 2021 Sep;507:108377. doi: 10.1016/j.carres.2021.108377. Epub 2021 Jun 16. [PubMed:34303197 ]
  5. Liangfei L, Yafeng Z, Kai X, Zheng X: Identification of a thermostable cellobiose 2-epimerase from Caldicellulosiruptor sp. Rt8.B8 and production of epilactose using Bacillus subtilis. J Sci Food Agric. 2021 May 24. doi: 10.1002/jsfa.11333. [PubMed:34031874 ]
  6. Jayaraman AB, Kandasamy T, Venkataraman D, S M: Rational design of Shewanella sp. l-arabinose isomerase for d-galactose isomerase activity under mesophilic conditions. Enzyme Microb Technol. 2021 Jun;147:109796. doi: 10.1016/j.enzmictec.2021.109796. Epub 2021 Mar 31. [PubMed:33992411 ]
  7. Durante M, Sgambellone S, Lucarini L, Failli P, Laurino A, Collotta D, Provensi G, Masini E, Collino M: D-Tagatose Feeding Reduces the Risk of Sugar-Induced Exacerbation of Myocardial I/R Injury When Compared to Its Isomer Fructose. Front Mol Biosci. 2021 Apr 13;8:650962. doi: 10.3389/fmolb.2021.650962. eCollection 2021. [PubMed:33928123 ]
  8. Bu Y, Zhang T, Jiang B, Chen J: Improved Performance of D-Psicose 3-Epimerase by Immobilisation on Amino-Epoxide Support with Intense Multipoint Attachment. Foods. 2021 Apr 11;10(4). pii: foods10040831. doi: 10.3390/foods10040831. [PubMed:33920442 ]
  9. Yoshida H, Yoshihara A, Kato S, Mochizuki S, Akimitsu K, Izumori K, Kamitori S: Crystal structure of a novel homodimeric l-ribulose 3-epimerase from Methylomonus sp. FEBS Open Bio. 2021 Jun;11(6):1621-1637. doi: 10.1002/2211-5463.13159. Epub 2021 May 1. [PubMed:33838083 ]
  10. Thomson GJ, Kakade P, Hirakawa MP, Ene IV, Bennett RJ: Adaptation to the dietary sugar D-tagatose via genome instability in polyploid Candida albicans cells. G3 (Bethesda). 2021 Apr 9. pii: 6219300. doi: 10.1093/g3journal/jkab110. [PubMed:33836061 ]
  11. Dai Y, Li M, Jiang B, Zhang T, Chen J: Whole-cell biosynthesis of d-tagatose from maltodextrin by engineered Escherichia coli with multi-enzyme co-expression system. Enzyme Microb Technol. 2021 Apr;145:109747. doi: 10.1016/j.enzmictec.2021.109747. Epub 2021 Jan 28. [PubMed:33750537 ]