Record Information
Version1.0
Creation date2010-04-08 22:04:50 UTC
Update date2019-11-27 17:04:27 UTC
Primary IDFDB001114
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha,alpha-Trehalose
DescriptionOccurs in fungi. EU and USA approved sweetener Trehalose is a disaccharide formed by a 1, 1-glucoside bond between two ?-glucose units. Because trehalose is formed by the bonding of two reducing groups, it has no capacity to reduce other compounds.; Trehalose was first isolated from ergot of rye. Emil Fischer first described the trehalose-hydrolyzing enzyme in yeast. Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of ?-D-glucopyranosyl-(1?1)-?-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). Trehalose is broken down by the enzyme trehalase into glucose. Trehalose has about 45% the sweetness of sucrose. Trehalose is less soluble than sucrose, except at high temperatures (>80 °C). Trehalose forms a rhomboid crystal as the dihydrate, and has 90% of the calorific content of sucrose in that form. Anhydrous forms of trehalose readily regain moisture to form the dihydrate. Anhydrous forms of trehalose can show interesting physical properties when heat-treated.; Trehalose, also known as mycose, is a 1-alpha (disaccharide) sugar found extensively but not abundantly in nature. It is thought to be implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation. The sugar is thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, generally lethal damage that would normally follow a dehydration/reyhdration cycle.; Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of alpha-D-glucopyranoglucopyranosyl-1,1-alpha-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). The enzyme trehalase, present but not abundant in most people, breaks it into two glucose molecules, which can then be readily absorbed in the gut.; Trehalose is an important components of insects circulating fluid.It acts as a storage form of insect circulating fluid and it is important in respiration.; Trehalose, also known as mycose, is a natural alpha-linked disaccharide formed by an ?, ?-1, 1-glucoside bond between two ?-glucose units. In 1832 Wiggers discovered trehalose in an ergot of rye and in 1859 Berthelot isolated it from trehala manna, a substance made by weevils, and named it trehalose. It can be synthesised by fungi, plants, and invertebrate animals. It is implicated in anhydrobiosis ? the ability of plants and animals to withstand prolonged periods of desiccation. It has high water retention capabilities and is used in food and cosmetics. The sugar is thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, lethal damage that would normally follow a dehydration/re-hydration cycle. Trehalose has the added advantage of being an antioxidant. Extracting trehalose used to be a difficult and costly process, but, recently, the Hayashibara company (Okayama, Japan) confirmed an inexpensive extraction technology from starch for mass production. Trehalose is currently being used for a broad spectrum of applications. alpha,alpha-Trehalose is found in bitter gourd, mushrooms, and garden tomato.
CAS Number99-20-7
Structure
Thumb
Synonyms
SynonymSource
(GLC)2ChEBI
alpha,Alpha'-trehaloseChEBI
alpha-D-GLCP-(11)-alpha-D-GLCPChEBI
alpha-D-Glucopyranosyl-alpha-D-glucopyranosideChEBI
alpha-D-TrehaloseChEBI
alpha-TrehaloseChEBI
D-(+)-TrehaloseChEBI
Ergot sugarChEBI
MycoseChEBI
a,Alpha'-trehaloseGenerator
Α,alpha'-trehaloseGenerator
a-D-GLCP-(11)-a-D-GLCPGenerator
Α-D-GLCP-(11)-α-D-GLCPGenerator
a-D-Glucopyranosyl-a-D-glucopyranosideGenerator
Α-D-glucopyranosyl-α-D-glucopyranosideGenerator
a-D-TrehaloseGenerator
Α-D-trehaloseGenerator
a-TrehaloseGenerator
Α-trehaloseGenerator
alpha,alpha-TrehaloseHMDB
D-Trehalose-anhydrousHMDB
delta-Trehalose-anhydrousHMDB
D-TrehaloseHMDB
Natural trehaloseHMDB
O-D-Glucopyranosyl-(1→1)-D-glucopyranosideHMDB
TrehaloseHMDB
alpha,alpha'-D-TrehaloseHMDB
alpha-D-Glucopyranosyl alpha-D-glucopyranosideHMDB
α,α'-D-TrehaloseHMDB
α,α-TrehaloseHMDB
α,α’-D-TrehaloseHMDB
α-D-Glucopyranosyl α-D-glucopyranosideHMDB
(Glc)2ChEBI
α-d-glucopyranoside, α-d-glucopyranosylbiospider
α-d-glucopyranosyl-α-d-glucopyranosidebiospider
α-d-trehalosebiospider
α-trehalosebiospider
α,α-trehalosebiospider
α,α'-trehalosebiospider
a-D-Glcp-(11)-a-D-glcpGenerator
a-D-Glucopyranosyl-a-D-glucopyranoside, 9CI, 8CIdb_source
a,a-TrehaloseGenerator
alpha-D-Glcp-(11)-alpha-D-glcpChEBI
Alpha-d-glucopyranosyl beta-d-glucopyranosidebiospider
Alpha,alpha-trehalosebiospider
Alpha,alpha'-trehalosebiospider
Alpha,beta-trehalosebiospider
D-(+)-trehalosebiospider
D-trehalose-anhydrousbiospider
Delta-trehalose-anhydrousbiospider
Hexopyranosyl hexopyranosidebiospider
Mushroom sugardb_source
Trehalose, dihydratebiospider
α-D-glcp-(11)-α-D-glcpGenerator
α-D-glucopyranosyl-α-D-glucopyranosideGenerator
α-D-trehaloseGenerator
α-trehaloseGenerator
α,alpha'-trehaloseGenerator
α,α-trehaloseGenerator
Predicted Properties
PropertyValueSource
logP-4.7ChemAxon
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.14 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H22O11
IUPAC name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol
InChI IdentifierInChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2
InChI KeyHDTRYLNUVZCQOY-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • 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 42.11%; H 6.48%; O 51.42%DFC
Melting PointMp 214-216° (anhyd.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +199 (H2O) (anhyd.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0j4m-0932000000-8d7c80edd7f55e92ea29View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9511000000-b710c7c4bd86fd5f1af0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9511000000-2e5f22e6ba282283a569View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9832000000-b3259de2e25ea7293565View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0wos-0921000000-68fb82f427417ec703a0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0j4m-0943000000-07c11d483e4278dc639aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0wmm-0953000000-b74403fa3ce6ce0339ebView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0i04-0932000000-8de0421184ae3291ea53View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-8932000000-c327fe31b8d3e86dd97dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (8 TMS)splash10-0j4l-0954000000-33e230d28780be607983View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0j4m-0932000000-8d7c80edd7f55e92ea29View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9511000000-b710c7c4bd86fd5f1af0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9511000000-2e5f22e6ba282283a569View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9832000000-b3259de2e25ea7293565View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wos-0921000000-68fb82f427417ec703a0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0j4m-0943000000-07c11d483e4278dc639aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wmm-0953000000-b74403fa3ce6ce0339ebView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i04-0932000000-8de0421184ae3291ea53View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8932000000-c327fe31b8d3e86dd97dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0j4l-0954000000-33e230d28780be607983View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i2d-0921000000-9e633378baf1645df2a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ni-9554000000-e418bec346785e269084View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2553419000-dd0bea0ade3ee46308dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-1901000000-865e9e390fac7d13c2f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9500000000-7d4c9de285c2872d2320View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-c71f25d08b875caff6b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-0019000000-3b4e276ff5686c841bddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fdx-8905000000-fafde7828ce0d63fe618View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fdx-8905000000-f4b4b3ad528ea3bf43c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-d382926500274fb84a46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-10524d7a715f8a0ed265View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0019000000-3b4e276ff5686c841bddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0903000000-8981579ae1dd58ba65c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1901000000-4c8ec381daa00b88a539View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-5900000000-89485b49a32afa256bdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-4918000000-df3152da1740bcb45d3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03mi-3901000000-c9e67703b1ef9ca4f8ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9600000000-b9d2971c377f79dd6238View in MoNA
MSMass Spectrum (Electron Ionization)splash10-022c-9100000000-33d1067ccb0cb2dda51dView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID7149
ChEMBL IDCHEMBL1236395
KEGG Compound IDC01083
Pubchem Compound ID7427
Pubchem Substance IDNot Available
ChEBI ID16551
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00975
CRC / DFC (Dictionary of Food Compounds) IDBTL34-B:BTL34-B
EAFUS IDNot Available
Dr. Duke IDTREHALOSE|ALPHA-ALPHA-TREHALOSE|MYCOSE
BIGG ID36774
KNApSAcK IDC00001152
HET IDTRE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTrehalose
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
Enzymes
NameGene NameUniProt ID
TrehalaseTREHO43280
Pathways
NameSMPDB LinkKEGG Link
Trehalose DegradationSMP00467 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.