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Palatinose

PubChem CID
439559
Structure
Palatinose_small.png
Palatinose_3D_Structure.png
Molecular Formula
Synonyms
  • Palatinose
  • Isomaltulose
  • 6-O-alpha-D-Glucopyranosyl-D-fructofuranose
  • Isomaltulose hydrate
  • (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy]oxane-3,4,5-triol
Molecular Weight
342.30 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
6-O-alpha-D-glucopyranosyl-D-fructofuranose is a glycosylfructose that is D-fructofuranose attached to a alpha-D-glucopyranosyl unit at position 6 via a glycosidic linkage. It is found in honey and sugarcane. It has a role as a sweetening agent, an animal metabolite and a plant metabolite.
Palatinose has been reported in Daphnia pulex, Pogostemon cablin, and Pseudo-nitzschia multistriata with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Palatinose.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
Glc(a1-6)Fruf
LINUCS
[][D-Fruf]{[(6+1)][a-D-Glcp]{}}
IUPAC
alpha-D-gluco-hexopyranosyl-(1->6)-D-arabino-hex-2-ulofuranose

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy]oxane-3,4,5-triol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C12H22O11/c13-1-4-6(15)8(17)9(18)11(22-4)21-2-5-7(16)10(19)12(20,3-14)23-5/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12?/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

PVXPPJIGRGXGCY-TZLCEDOOSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC[C@@H]2[C@H]([C@@H](C(O2)(CO)O)O)O)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C12H22O11
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

58166-27-1

3.3.2 European Community (EC) Number

3.3.3 ChEBI ID

3.3.4 KEGG ID

3.3.5 Metabolomics Workbench ID

3.3.6 Nikkaji Number

3.3.7 Wikidata

3.3.8 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • 6-O alpha-D-glucopyranosyl-D-fructose
  • D-fructose, 6-O-alpha-D-glucopyranosyl-, monohydrate
  • isomaltulose
  • isomaltulose anhydrous
  • isomaltulose monohydrate
  • palatinose
  • palatinose monohydrate

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
342.30 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-4.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
11
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
342.11621151 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
342.11621151 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
190 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
395
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
8
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Experimental Properties

4.2.1 Collision Cross Section

177.9 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

176 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

177.6 Ų [M+K]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

177.31 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

172.6 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

176.2 Ų [M+Na]+

175.4 Ų [M-H]-

177.7 Ų [M+K]+

S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

5 Spectral Information

5.1 Mass Spectrometry

5.1.1 GC-MS

MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Leco Pegasus IV
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

103 100

147 96.10

204 75.88

217 69.67

129 54.35

Thumbnail
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5.1.2 MS-MS

NIST Number
1052481
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M-H]-
Precursor m/z
341.1089
Total Peaks
24
m/z Top Peak
179.1
m/z 2nd Highest
221.1
m/z 3rd Highest
323.1
Thumbnail
Thumbnail

5.1.3 LC-MS

1 of 5
View All
Authors
Matsuda F, Suzuki M, Sawada Y, Plant Science Center, RIKEN.
Instrument
UPLC Q-Tof Premier, Waters
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
Ramp 5-60 V
Fragmentation Mode
LOW-ENERGY CID
Precursor m/z
343.12401
Precursor Adduct
[M+H]+
Top 5 Peaks

192.9773 999

276.9304 684

278.9421 562

178.9655 410

296.9911 377

Thumbnail
Thumbnail
License
CC BY-SA
2 of 5
View All
Authors
Matsuda F, Suzuki M, Sawada Y, Plant Science Center, RIKEN.
Instrument
UPLC Q-Tof Premier, Waters
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
Ramp 5-60 V
Fragmentation Mode
LOW-ENERGY CID
Precursor m/z
341.10841
Precursor Adduct
[M-H]-
Top 5 Peaks

101.0234 999

179.0539 848

71.0148 822

89.0237 598

221.0646 583

Thumbnail
Thumbnail
License
CC BY-SA

5.1.4 Other MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
341.36
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
negative
Collision Energy
40
Top 5 Peaks
89 100
Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
341.108
Instrument
qTof
Ionization Mode
negative
Top 5 Peaks

59.017410 100

89.026062 75.46

89.028717 62.58

59.019581 62.58

71.017311 62.58

Thumbnail
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7 Chemical Vendors

8 Drug and Medication Information

8.1 Clinical Trials

8.1.1 ClinicalTrials.gov

9 Pharmacology and Biochemistry

9.1 Biochemical Reactions

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 KEGG: Metabolite

13.4 NORMAN Suspect List Exchange Classification

13.5 CCSBase Classification

13.6 LOTUS Tree

13.7 Glycan Naming and Subsumption Ontology (GNOme)

13.8 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  2. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Palatinose
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  3. ChEBI
    6-O-alpha-D-glucopyranosyl-D-fructofuranose
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18394
  4. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  5. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  6. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  7. Japan Chemical Substance Dictionary (Nikkaji)
  8. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  9. Natural Product Activity and Species Source (NPASS)
  10. MassBank Europe
  11. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  12. Metabolomics Workbench
  13. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  14. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  15. Springer Nature
  16. Wikidata
    6-O-alpha-D-glucopyranosyl-D-fructofuranose
    https://www.wikidata.org/wiki/Q27103048
  17. Wikipedia
  18. PubChem
  19. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  20. Glycan Naming and Subsumption Ontology (GNOme)
    GNOme
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
  23. NCBI
CONTENTS