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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H32O16.2H2O
Molecular Weight 540.4676
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MELEZITOSE DIHYDRATE

SMILES

O.O.OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]1O

InChI

InChIKey=LNVIPYYEBMNJIL-ZWELICPFSA-N
InChI=1S/C18H32O16.2H2O/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;2*1H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15+,16-,17-,18+;;/m1../s1

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/29026120 | https://www.ncbi.nlm.nih.gov/pubmed/27624065 |

Melezitose is a nonreducing trisaccharide sugar that is produced by many plant sap-eating insects, including aphids such as Cinara pilicornis. Melezitose 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. Melezitose fatty acid monoesters are potential surfactants, that may solubilize hydrophobic drugs for parenteral formulations.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Yeast strains from Livingston Island, Antarctica.
2001
Polyphasic investigation of the diversity within Lactobacillus plantarum related strains revealed two L. plantarum subgroups.
2001 Dec
Responses of the ant Lasius niger to various compounds perceived as sweet in humans: a structure-activity relationship study.
2001 Mar
Purification and characterisation of an extracellular fructan beta-fructosidase from a Lactobacillus pentosus strain isolated from fermented fish.
2002 Apr
Gustatory perception and metabolic utilization of sugars by Myrmica rubra ant workers.
2003 Aug
Cloning and characterization of two alpha-glucosidases from Bifidobacterium adolescentis DSM20083.
2003 Mar
Different food sources affect the gustatory response of Anaphes iole, an egg parasitoid of Lygus Spp.
2003 May
Enterococcus phoeniculicola sp. nov., a novel member of the enterococci isolated from the uropygial gland of the Red-billed Woodhoopoe, Phoeniculus purpureus.
2003 May
Specificity of yeast (Saccharomyces cerevisiae) in removing carbohydrates by fermentation.
2003 May 1
Cotton honeydew (Gossypium hirsutum L.) extract offers very interesting properties for hair cosmetics and care products.
2005
Prevotella multisaccharivorax sp. nov., isolated from human subgingival plaque.
2005 Sep
Determination of sugar compounds in atmospheric aerosols by liquid chromatography combined with positive electrospray ionization mass spectrometry.
2006 Feb 24
Isolation and characterization of Streptococcus sp. from diseased flounder (Paralichthys olivaceus) in Jeju Island.
2006 Mar
Hydrolysis kinetics of trisaccharides consisting of glucose, galactose, and fructose residues in subcritical water.
2006 Sep-Oct
History and evolution of antibiotic resistance in coagulase-negative staphylococci: Susceptibility profiles of new anti-staphylococcal agents.
2007 Dec
High susceptibility of Bt maize to aphids enhances the performance of parasitoids of lepidopteran pests.
2007 Jul 11
Application of biselective refocusing soft pulses to the simplification of heteronuclear correlation spectra.
2008 Feb
Behavioral analyses of sugar processing in choice, feeding, and learning in larval Drosophila.
2008 Jul
Virulent clones of Klebsiella pneumoniae: identification and evolutionary scenario based on genomic and phenotypic characterization.
2009
Indian Bt cotton varieties do not affect the performance of cotton aphids.
2009
Genome sequence and comparative genome analysis of Lactobacillus casei: insights into their niche-associated evolution.
2009 Jul 14
Isolation and characterization of the equol-producing bacterium Slackia sp. strain NATTS.
2010 Apr
Highly efficient and mild method for regioselective de-O-benzylation of saccharides by Co2(CO)8-Et3SiH-CO reagent system.
2010 Feb 5
Actinomyces timonensis sp. nov., isolated from a human clinical osteo-articular sample.
2010 Jul
Metabolic profiling reveals local and systemic responses of host plants to nematode parasitism.
2010 Jun 1
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Plastic insect cage (height: 12.5 cm; diam: 10.0 cm) was provided with four calibrated glass micropipettes (5.0 μl, Blaubrand Intramark, Wertheim, Germany) filled with 4.0 μl of the test sugar solution (Melezitose) and inert mineral oil overlay (1.0 μl) to minimize evaporation. These capillaries were inserted through the lid (at the corners of a square of 4.5 × 4.5 cm, in the middle of the lid) via truncated 200 μl yellow pipette tips. To meet the water requirements of the parasitoids, a filter paper imbibed with 500 μl of sterile demineralized water was placed at the bottom of the cage at the start of the experiment, and supplemented with another 500 μl of water each day for the longevity experiments. To allow entry of air, the lid of the cage was pierced and covered with a fine mesh (2.5 × 2.5 cm; mesh size 0.27 × 0.88 mm). For each experiment, after being subjected to a dark period of 8 h, five replicates of 15 adult parasitoids were released in each cage. Each experiment also included an identical CAFE chamber without parasitoids to determine evaporative losses, which were subtracted from experimental readings. All experiments were conducted under controlled conditions of 22 °C, 70 % RH and a 16:8 h L:D cycle, starting with the light period.
Name Type Language
MELEZITOSE DIHYDRATE
MI  
Common Name English
O-.ALPHA.-D-GLUCOPYRANOSYL-(1->3)-.BETA.-D-FRUCTOFURANOSYL-.ALPHA.-D-GLUCOPYRANOSIDE DIHYDRATE
Systematic Name English
MELEZITOSE DIHYDRATE [MI]
Common Name English
.ALPHA.-D-GLUCOPYRANOSIDE, O-.ALPHA.-D-GLUCOPYRANOSYL-(1->3)-.BETA.-D-FRUCTOFURANOSYL, DIHYDRATE
Systematic Name English
MELEZITOSE DIHYDRATE, (+)-
Common Name English
Code System Code Type Description
MERCK INDEX
m7157
Created by admin on Sat Dec 16 10:06:17 GMT 2023 , Edited by admin on Sat Dec 16 10:06:17 GMT 2023
PRIMARY Merck Index
PUBCHEM
67660249
Created by admin on Sat Dec 16 10:06:17 GMT 2023 , Edited by admin on Sat Dec 16 10:06:17 GMT 2023
PRIMARY
FDA UNII
D12C11K0M0
Created by admin on Sat Dec 16 10:06:17 GMT 2023 , Edited by admin on Sat Dec 16 10:06:17 GMT 2023
PRIMARY
CAS
6147-31-5
Created by admin on Sat Dec 16 10:06:17 GMT 2023 , Edited by admin on Sat Dec 16 10:06:17 GMT 2023
PRIMARY
CAS
207511-10-2
Created by admin on Sat Dec 16 10:06:17 GMT 2023 , Edited by admin on Sat Dec 16 10:06:17 GMT 2023
NON-SPECIFIC STOICHIOMETRY