Names | |
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IUPAC name
1-O-α-D-Glucopyranosyl-D-fructose
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.051.967 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C12H22O11 | |
Molar mass | 342.297 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trehalulose is a disaccharide made up of a molecule of fructose bound to a molecule of glucose. Like isomaltulose, it is a structural isomer of sucrose that is present in small quantities in honey.[1] It makes up 50% of sugars in the honeydew of silverleaf whiteflies[2][3] and is synthesised from sucrose by some bacteria,[4][5] such as Protaminombacter rubrum.[6][1] Because the anomeric carbon of the fructose moiety is not involved in the glycosidic bond, it is a reducing sugar.[6]
Because the fructose and glucose molecules are linked by a 1,1 glycosidic bond, which is more stable than the 1,2 glycosidic bond in sucrose, it is broken down more slowly than sucrose in the small intestine, giving it a lower glycemic index.[6] This more stable bond also means that it cannot be utilised by Streptococcus mutans, and it is therefore non-cariogenic.[7]
Unlike isomaltulose, trehalulose strongly resists crystallisation, and forms an amorphous solid when dried. Its sweetness relative to sucrose has been estimated as between 0.4[8] and 0.7.[9]
It has a specific rotation of °.[1]
In 2020 researchers at the University of Queensland found that some species of stingless bee in Australia, Malaysia, and Brazil produce honey containing between 13% and 44% trehalulose rather than the usual glucose and fructose. The university's findings supported the long-standing claims of Indigenous Australian people that native honey is beneficial for human health.[10][11] In 2021 the same researchers discovered that the bees convert all sucrose from nectar into trehalulose.[12]