Structure via PubChem · Public domain (PubChem)
melezitose
Sign in to saveAlso known as Melizitose, O-alpha-D-glucopyranosyl-(1-3)-beta-D-fructofuranosyl-alpha-D-glucopyranoside, (2R,3R,4S,5S,6R)-2-{[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol, D-melezitose, melicitose, D-(+)-melezitose
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. This is useful to the aphids as they have a symbiotic relationship with ants. Melezitose can be partially hydrolyzed to glucose and turanose the lat
Chemical data
- Formula
- C18H32O16
- Molecular weight
- 504.4 g/mol
- IUPAC name
- (2R,3R,4S,5S,6R)-2-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
- SMILES
- C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O)O)O)O)O
- InChIKey
- QWIZNVHXZXRPDR-WSCXOGSTSA-N
- XLogP
- -5.8
- Polar surface area
- 269 Ų
- H-bond donors
- 11
- H-bond acceptors
- 16
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 504.169035
Show 3 more facts
- chemical formula
- C₁₈H₃₂O₁₆
- isomeric SMILES
- C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O)O)O)O)O
- canonical SMILES
- C(C1C(C(C(C(O1)OC2C(C(OC2(CO)OC3C(C(C(C(O3)CO)O)O)O)CO)O)O)O)O)O
Sources (2)
via Wikidata · CC0
~1 min read
Article
1 sectionsContents
- References
{{Chembox | Verifiedfields = changed | verifiedrevid = 458280958 | ImageFile=Melezitose.png | ImageSize=200px | IUPACName=α-D-Glucopyranosyl α-D-glucopyranosyl-(1→3)-β-D-fructofuranoside | SystematicName=(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] | OtherNames=Melicitose |Section1= |Section2= |Section3= }}
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. 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.