Melezitose

Melezitose

Names
IUPAC name (2R,3R,4S,5S,6R)-2-[[(2S,3S,4R,5R)-4-Hydroxy-2,5-bis(hydroxymethyl)-3-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-2-tetrahydrofuranyl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
Other names Melicitose
Identifiers
CAS Number	597-12-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6731
ChEMBL	ChEMBL386007
ChemSpider	83787
ECHA InfoCard	100.008.997
PubChem CID	92817
UNII	T4T25QN29L
CompTox Dashboard (EPA)	DTXSID20883458
InChI InChI=1S/C18H32O16/c19-1-5-8(23)11(26)13(28)16(30-5)32-15-10(25)7(3-21)33-18(15,4-22)34-17-14(29)12(27)9(24)6(2-20)31-17/h5-17,19-29H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15+,16-,17-,18+/m1/s1 Key: QWIZNVHXZXRPDR-WSCXOGSTSA-N InChI=1/C18H32O16/c19-1-5-8(23)11(26)13(28)16(30-5)32-15-10(25)7(3-21)33-18(15,4-22)34-17-14(29)12(27)9(24)6(2-20)31-17/h5-17,19-29H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15+,16-,17-,18+/m1/s1 Key: QWIZNVHXZXRPDR-WSCXOGSTBR
SMILES O1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O[C@@]3(O[C@@H]([C@@H](O)[C@@H]3O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)CO)CO
Properties
Chemical formula	C18H32O16
Molar mass	504.438 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Melezitose, also spelled melicitose, is a nonreducing trisaccharide sugar that is produced by many plant sap eating insects, including aphids such as Cinara pilicornis, by an enzyme reaction. This is beneficial to the insects, as it reduces the stress of osmosis by reducing their own water potential. The melezitose is part of the honeydew which acts as an attractant for ants and also as a food for bees.^[1] This is useful to the lice as they have a symbiotic relationship with ants. Melezitose can be partially hydrolyzed to glucose and turanose the latter of which is an isomer of sucrose.

Honeycomb filled with Melezitose

References