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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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H32O16
Molecular Weight 504.4371
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 14 / 14
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Complete genome sequence of Ilyobacter polytropus type strain (CuHbu1).
2010-12-15
Molecular epidemiology of zoonotic streptococcosis/lactococcosis in rainbow trout (Oncorhynchus mykiss) aquaculture in Iran.
2010-12
Determination of cross sections by overtone mobility spectrometry: evidence for loss of unstable structures at higher overtones.
2010-09-30
Characterization of a novel Lactobacillus species closely related to Lactobacillus johnsonii using a combination of molecular and comparative genomics methods.
2010-09-17
Clostridium arbusti sp. nov., an anaerobic bacterium isolated from pear orchard soil.
2010-09
Thermal diffusion of oligosaccharide solutions: the role of chain length and structure.
2010-08-26
Complete genome sequence of Olsenella uli type strain (VPI D76D-27C).
2010-08-20
Isolation and characterization of lactic acid bacteria strains with ornithine producing capacity from natural sea salt.
2010-08
Actinomyces timonensis sp. nov., isolated from a human clinical osteo-articular sample.
2010-07
Metabolic profiling reveals local and systemic responses of host plants to nematode parasitism.
2010-06-01
Isolation and characterization of the equol-producing bacterium Slackia sp. strain NATTS.
2010-04
Complete genome sequence of Kribbella flavida type strain (IFO 14399).
2010-03-30
Complete genome sequence of Geodermatophilus obscurus type strain (G-20).
2010-03-30
A novel high-affinity sucrose transporter is required for virulence of the plant pathogen Ustilago maydis.
2010-02-09
Highly efficient and mild method for regioselective de-O-benzylation of saccharides by Co2(CO)8-Et3SiH-CO reagent system.
2010-02-05
Complete genome sequence of Alicyclobacillus acidocaldarius type strain (104-IA).
2010-01-28
Cold-adapted yeasts from Antarctica and the Italian Alps-description of three novel species: Mrakia robertii sp. nov., Mrakia blollopis sp. nov. and Mrakiella niccombsii sp. nov.
2010-01
Molecular and cellular designs of insect taste receptor system.
2010
Complete genome sequence of Stackebrandtia nassauensis type strain (LLR-40K-21).
2009-12-30
PERSOONIAL Reflections.
2009-12
Isolation and characterization of a strain of Lichtheimia corymbifera (ex Absidia corymbifera) from a case of bovine abortion.
2009-11-30
Complete genome sequence of Kangiella koreensis type strain (SW-125).
2009-11-22
Complete genome sequence of Atopobium parvulum type strain (IPP 1246).
2009-09-23
Evaluation of genotypic and phenotypic methods for differentiation of the members of the Anginosus group streptococci.
2009-09
Genome sequence and comparative genome analysis of Lactobacillus casei: insights into their niche-associated evolution.
2009-07-14
Overtone mobility spectrometry: part 2. Theoretical considerations of resolving power.
2009-05
Overtone mobility spectrometry: part 1. Experimental observations.
2009-05
High-resolution ion cyclotron mobility spectrometry.
2009-02-15
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
Behavioral analyses of sugar processing in choice, feeding, and learning in larval Drosophila.
2008-07
Preparation of partially benzylated mono-, di-, and trisaccharides by selective cleavage of the beta-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides under acidic conditions.
2008-06-09
Positive-ion ESI mass spectrometry of regioisomeric nonreducing oligosaccharide fatty acid monoesters: in-source fragmentation of sodium adducts.
2008-05
Reactivity of melezitose and raffinose under Mitsunobu reaction conditions.
2008-04-07
Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides.
2008-04-07
Application of biselective refocusing soft pulses to the simplification of heteronuclear correlation spectra.
2008-02
Characteristic fragmentation patterns of the trimethylsilyl and trimethylsilyl-oxime derivatives of various saccharides as obtained by gas chromatography coupled to ion-trap mass spectrometry.
2008-01-04
Environmental isolation of black yeast-like fungi involved in human infection.
2008
Physiological and molecular adaptations to drought in Andean potato genotypes.
2008
History and evolution of antibiotic resistance in coagulase-negative staphylococci: Susceptibility profiles of new anti-staphylococcal agents.
2007-12
Nutritional ecology of a parasitic wasp: food source affects gustatory response, metabolic utilization, and survivorship.
2007-12
High susceptibility of Bt maize to aphids enhances the performance of parasitoids of lepidopteran pests.
2007-07-11
Description of a new species, Bifidobacterium crudilactis sp. nov., isolated from raw milk and raw milk cheeses.
2007-07
Analysis of sugars and sugar polyols in atmospheric aerosols by chloride attachment in liquid chromatography/negative ion electrospray mass spectrometry.
2007-04-01
Labrys okinawensis sp. nov. and Labrys miyagiensis sp. nov., budding bacteria isolated from rhizosphere habitats in Japan, and emended descriptions of the genus Labrys and Labrys monachus.
2007-03
Hydrolysis kinetics of trisaccharides consisting of glucose, galactose, and fructose residues in subcritical water.
2006-10-07
The stability of insulin in solid formulations containing melezitose and starch. Effects of processing and excipients.
2006-07
[Isolation and identification of a bacterial strain JS018 capable of degrading several kinds of organophosphate pesticides].
2006-06
Effect of dietary honey on intestinal microflora and toxicity of mycotoxins in mice.
2006-03-14
Screening for new compounds with antiherpes activity.
1984-10
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:02:08 GMT 2025
Edited
by admin
on Mon Mar 31 23:02:08 GMT 2025
Record UNII
D12C11K0M0
Record Status Validated (UNII)
Record Version
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Name Type Language
MELEZITOSE DIHYDRATE
MI  
Common Name English
MELEZITOSE DIHYDRATE [MI]
Preferred Name English
O-.ALPHA.-D-GLUCOPYRANOSYL-(1->3)-.BETA.-D-FRUCTOFURANOSYL-.ALPHA.-D-GLUCOPYRANOSIDE DIHYDRATE
Systematic 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 Mon Mar 31 23:02:09 GMT 2025 , Edited by admin on Mon Mar 31 23:02:09 GMT 2025
PRIMARY Merck Index
PUBCHEM
67660249
Created by admin on Mon Mar 31 23:02:09 GMT 2025 , Edited by admin on Mon Mar 31 23:02:09 GMT 2025
PRIMARY
FDA UNII
D12C11K0M0
Created by admin on Mon Mar 31 23:02:09 GMT 2025 , Edited by admin on Mon Mar 31 23:02:09 GMT 2025
PRIMARY
CAS
6147-31-5
Created by admin on Mon Mar 31 23:02:09 GMT 2025 , Edited by admin on Mon Mar 31 23:02:09 GMT 2025
PRIMARY
CAS
207511-10-2
Created by admin on Mon Mar 31 23:02:09 GMT 2025 , Edited by admin on Mon Mar 31 23:02:09 GMT 2025
NON-SPECIFIC STOICHIOMETRY
Related Record Type Details
ANHYDROUS->SOLVATE