Melezitose

Melezitose

Names
IUPAC name α-D-Glucopyranosyl α-D-glucopyranosyl-(1→3)-β-D-fructofuranoside
Systematic IUPAC name (2R,2′R,3R,3′R,4S,4′S,5S,5′S,6R,6′R)-2,2′-{[(2S,3S,4R,5R)-4-Hydroxy-2,5-bis(hydroxymethyl)oxolane-2,3-diyl]bis(oxy)}bis[6-(hydroxymethyl)oxane-3,4,5-triol]
Other names Melicitose
Identifiers
CAS Number	597-12-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6731^Y
ChEMBL	ChEMBL386007^Y
ChemSpider	83787^Y
ECHA InfoCard	100.008.997
PubChem CID	92817
UNII	T4T25QN29L^Y
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^Y Key: QWIZNVHXZXRPDR-WSCXOGSTSA-N^Y 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). N verify (what is ^YN ?) Infobox references

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 although it is not easily digestible by bees.^[1] This is useful to the aphids 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

1. Fischer, M. K; Shingleton, A. W (2001). "Host plant and ants influence the honeydew sugar composition of aphids". Functional Ecology. 15 (4): 544. doi:10.1046/j.0269-8463.2001.00550.x.