1.0 2010-04-08 22:04:50 UTC 2019-11-26 02:55:57 UTC FDB001114 alpha,alpha-Trehalose Occurs 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. (Glc)2 α-d-glucopyranoside, α-d-glucopyranosyl α-d-glucopyranosyl-α-d-glucopyranoside α-d-trehalose α-trehalose α,α-trehalose α,α'-trehalose a-D-Glcp-(11)-a-D-glcp a-D-Glucopyranosyl-a-D-glucopyranoside a-D-Glucopyranosyl-a-D-glucopyranoside, 9CI, 8CI a-D-Trehalose a-Trehalose a,a-Trehalose a,Alpha'-trehalose alpha-D-Glcp-(11)-alpha-D-glcp Alpha-d-glucopyranosyl beta-d-glucopyranoside alpha-D-Glucopyranosyl-alpha-D-glucopyranoside alpha-D-Trehalose alpha-Trehalose Alpha,alpha-trehalose Alpha,alpha'-trehalose Alpha,beta-trehalose D-(+)-trehalose D-trehalose-anhydrous Delta-trehalose-anhydrous Ergot sugar Hexopyranosyl hexopyranoside Mushroom sugar Mycose Natural trehalose Trehalose Trehalose, dihydrate α-D-glcp-(11)-α-D-glcp α-D-glucopyranosyl-α-D-glucopyranoside α-D-trehalose α-trehalose α,alpha'-trehalose α,α-trehalose C12H22O11 342.2965 342.116211546 (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 α,α'-trehalose 99-20-7 OCC1OC(OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O InChI=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 HDTRYLNUVZCQOY-UHFFFAOYSA-N 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. O-glycosyl compounds Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Disaccharides Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Acetal Alcohol Aliphatic heteromonocyclic compound Disaccharide Hydrocarbon derivative O-glycosyl compound Organoheterocyclic compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Disaccharides trehalose Solid logp -2.98 ALOGPS logs 0.24 ALOGPS solubility 5.92e+02 g/l ALOGPS melting_point Mp 214-216° (anhyd.) logp -4.7 ChemAxon pka_strongest_acidic 11.91 ChemAxon pka_strongest_basic -3 ChemAxon iupac (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 ChemAxon average_mass 342.2965 ChemAxon mono_mass 342.116211546 ChemAxon smiles OCC1OC(OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O ChemAxon formula C12H22O11 ChemAxon inchi InChI=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 ChemAxon inchikey HDTRYLNUVZCQOY-UHFFFAOYSA-N ChemAxon polar_surface_area 189.53 ChemAxon refractivity 68.34 ChemAxon polarizability 31.14 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Trehalose Degradation SMP00467 Specdb::EiMs 1987 Specdb::NmrTwoD 1051 Specdb::NmrTwoD 1568 Specdb::CMs 689 Specdb::CMs 690 Specdb::CMs 691 Specdb::CMs 692 Specdb::CMs 693 Specdb::CMs 694 Specdb::CMs 695 Specdb::CMs 696 Specdb::CMs 697 Specdb::CMs 2094 Specdb::CMs 2607 Specdb::CMs 30183 Specdb::CMs 30278 Specdb::CMs 30279 Specdb::CMs 30280 Specdb::CMs 30281 Specdb::CMs 30282 Specdb::CMs 30283 Specdb::CMs 30702 Specdb::CMs 30780 Specdb::CMs 31273 Specdb::CMs 32348 Specdb::CMs 37872 Specdb::CMs 137739 Specdb::CMs 145473 Specdb::NmrOneD 1289 Specdb::NmrOneD 1627 Specdb::NmrOneD 4720 Specdb::NmrOneD 8142 Specdb::NmrOneD 8143 Specdb::NmrOneD 8144 Specdb::NmrOneD 8145 Specdb::NmrOneD 8146 Specdb::NmrOneD 8147 Specdb::NmrOneD 8148 Specdb::NmrOneD 8149 Specdb::NmrOneD 8150 Specdb::NmrOneD 8151 Specdb::NmrOneD 8152 Specdb::NmrOneD 8153 Specdb::NmrOneD 8154 Specdb::NmrOneD 8155 Specdb::NmrOneD 8156 Specdb::NmrOneD 8157 Specdb::NmrOneD 8158 Specdb::NmrOneD 8159 Specdb::NmrOneD 8160 Specdb::NmrOneD 8161 Specdb::NmrOneD 166427 Specdb::MsMs 1372 Specdb::MsMs 1373 Specdb::MsMs 1374 Specdb::MsMs 5023 Specdb::MsMs 5024 Specdb::MsMs 178527 Specdb::MsMs 178528 Specdb::MsMs 178529 Specdb::MsMs 180846 Specdb::MsMs 180847 Specdb::MsMs 180848 Specdb::MsMs 439058 Specdb::MsMs 440059 Specdb::MsMs 447544 Specdb::MsMs 448006 Specdb::MsMs 2231894 Specdb::MsMs 2232292 Specdb::MsMs 2234330 Specdb::MsMs 2234630 Specdb::MsMs 2236495 Specdb::MsMs 2236868 Specdb::MsMs 2244854 Specdb::MsMs 2245273 Specdb::MsMs 2246894 Specdb::MsMs 2247386 HMDB00975 16551 TRE #<Reference:0x0000559ad76e2608> #<Reference:0x0000559ad76e2450> #<Reference:0x0000559ad76e2270> #<Reference:0x0000559ad76e2068> #<Reference:0x0000559ad76e1eb0> #<Reference:0x0000559ad76e1cd0> #<Reference:0x0000559ad76e1ac8> #<Reference:0x0000559ad76e1910> #<Reference:0x0000559ad76e1730> #<Reference:0x0000559ad76e1528> #<Reference:0x0000559ad76e1370> #<Reference:0x0000559ad76e1190> #<Reference:0x0000559ad76e0f88> #<Reference:0x0000559ad76e0dd0> #<Reference:0x0000559ad76e0bf0> #<Reference:0x0000559ad76e09c0> #<Reference:0x0000559ad76e07e0> #<Reference:0x0000559ad76e0628> Beer Type 2 specific 0.0 0.0 0.0 mg/100 g Bitter gourd Type 1 specific Momordica charantia 3673 Common mushroom Type 1 specific Agaricus bisporus 5341 Garden tomato Type 1 specific Solanum lycopersicum 4081 Grape wine Type 2 specific 0.0 0.0 0.0 mg/100 g Mushrooms Unknown generic Oyster mushroom Type 1 specific Pleurotus ostreatus 5322 Trehalase O43280 TREH