Record Information
Version1.0
Creation date2010-04-08 22:04:50 UTC
Update date2018-01-23 18:47:59 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
a-D-Glucopyranosyl b-D-glucopyranosideHMDB
b-D-Glucopyranosyl a-D-glucopyranoside, 9ci, 8ciHMDB
(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-glucopyranosideGenerator
a-D-Glucopyranosyl-a-D-glucopyranoside, 9CI, 8CIdb_source
a-D-TrehaloseGenerator
a-TrehaloseGenerator
a,a-TrehaloseGenerator
a,Alpha'-trehaloseGenerator
alpha-D-Glcp-(11)-alpha-D-glcpChEBI
Alpha-d-glucopyranosyl beta-d-glucopyranosidebiospider
alpha-D-Glucopyranosyl-alpha-D-glucopyranosideChEBI
alpha-D-TrehaloseChEBI
alpha-TrehaloseChEBI
Alpha,alpha-trehalosebiospider
Alpha,alpha'-trehalosebiospider
Alpha,beta-trehalosebiospider
D-(+)-trehalosebiospider
D-trehalose-anhydrousbiospider
Delta-trehalose-anhydrousbiospider
Ergot sugarbiospider
Hexopyranosyl hexopyranosidebiospider
Mushroom sugardb_source
Mycosedb_source
Natural trehalosebiospider
Trehalosedb_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
Water Solubility592 g/LALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS0.24ALOGPS
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
Polarizability31.6 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H22O11
IUPAC name2-(hydroxymethyl)-6-{[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
DescriptionThis compound 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
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-MS (8 TMS)splash10-0hfx-0952000000-688a884a9a66ba7442b5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0iu0-7945000000-36714ff513c76f5ade98View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-3331119000-c2c2da6561fd9969b032View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0903000000-9534119d9b63c29cfd8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1901000000-2c8c8e367ff76886eeadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-5900000000-49e74a7c791f045fb7efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0903000000-9534119d9b63c29cfd8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1901000000-2c8c8e367ff76886eeadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-5900000000-49e74a7c791f045fb7efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-2917000000-da0f6c8de528721cec42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03mi-3901000000-7b491148c0f261acca3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9700000000-cbbcb43440c1144da812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-2917000000-da0f6c8de528721cec42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03mi-3901000000-7b491148c0f261acca3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9700000000-cbbcb43440c1144da812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0903000000-9534119d9b63c29cfd8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1901000000-2c8c8e367ff76886eeadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-5900000000-49e74a7c791f045fb7efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-2917000000-da0f6c8de528721cec42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03mi-3901000000-7b491148c0f261acca3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9700000000-cbbcb43440c1144da812View in MoNA
MSMass Spectrum (Electron Ionization)splash10-022c-9100000000-33d1067ccb0cb2dda51dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C 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
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.