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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
Polyphasic investigation of the diversity within Lactobacillus plantarum related strains revealed two L. plantarum subgroups.
2001 Dec
Metschnikowia lochheadii and Metschnikowia drosophilae, two new yeast species isolated from insects associated with flowers.
2001 Feb
Characterization of two novel saccharolytic, anaerobic thermophiles, Thermoanaerobacterium polysaccharolyticum sp. nov. and Thermoanaerobacterium zeae sp. nov., and emendation of the genus Thermoanaerobacterium.
2001 Mar
Purification and characterisation of an extracellular fructan beta-fructosidase from a Lactobacillus pentosus strain isolated from fermented fish.
2002 Apr
Molecular cloning and expression in Escherichia coli of an exo-levanase gene from the endophytic bacterium Gluconacetobacter diazotrophicus SRT4.
2002 Jul
Purification and characterization of acid trehalase from muscle of Ascaris suum (Nematoda).
2003 Sep
Nutrient composition of larval nectar secretions from three species of myrmecophilous butterflies.
2005 Dec
Sugar convertibility in the parasitoid Cotesia glomerata (Hymenoptera: Braconidae).
2005 Dec
Microspore embryogenesis and the development of a double haploidy protocol for cow cockle (Saponaria vaccaria).
2006 Apr
Determination of sugar compounds in atmospheric aerosols by liquid chromatography combined with positive electrospray ionization mass spectrometry.
2006 Feb 24
Hydrolysis kinetics of trisaccharides consisting of glucose, galactose, and fructose residues in subcritical water.
2006 Sep-Oct
Analysis of sugars and sugar polyols in atmospheric aerosols by chloride attachment in liquid chromatography/negative ion electrospray mass spectrometry.
2007 Apr 1
History and evolution of antibiotic resistance in coagulase-negative staphylococci: Susceptibility profiles of new anti-staphylococcal agents.
2007 Dec
Description of a new species, Bifidobacterium crudilactis sp. nov., isolated from raw milk and raw milk cheeses.
2007 Jul
High susceptibility of Bt maize to aphids enhances the performance of parasitoids of lepidopteran pests.
2007 Jul 11
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 Mar
Environmental isolation of black yeast-like fungi involved in human infection.
2008
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
Complete genome sequence of Stackebrandtia nassauensis type strain (LLR-40K-21).
2009 Dec 30
Highly efficient and mild method for regioselective de-O-benzylation of saccharides by Co2(CO)8-Et3SiH-CO reagent system.
2010 Feb 5
A novel high-affinity sucrose transporter is required for virulence of the plant pathogen Ustilago maydis.
2010 Feb 9
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 Sat Dec 16 10:06:17 GMT 2023
Edited
by admin
on Sat Dec 16 10:06:17 GMT 2023
Record UNII
D12C11K0M0
Record Status Validated (UNII)
Record Version
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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
Related Record Type Details
ANHYDROUS->SOLVATE