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3,4,6-tri-O-acetylglucal

PubChem CID
102891
Structure
3,4,6-tri-O-acetylglucal_small.png
3,4,6-tri-O-acetylglucal_3D_Structure.png
Molecular Formula
Synonyms
  • 3,4,6-tri-O-Acetyl-D-glucal
  • Tri-O-acetylglucal
  • Triacetyl-D-glucal
  • 3,4,6-Tri-O-acetylglucal
  • D-Glucal triacetate
Molecular Weight
272.25 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
See also: 3,4,6-Tri-O-acetyl-D-galactal (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
3,4,6-tri-O-acetylglucal.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3,4-diacetyloxy-3,4-dihydro-2H-pyran-2-yl)methyl acetate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C12H16O7/c1-7(13)17-6-11-12(19-9(3)15)10(4-5-16-11)18-8(2)14/h4-5,10-12H,6H2,1-3H3
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

LLPWGHLVUPBSLP-UHFFFAOYSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CC(=O)OCC1C(C(C=CO1)OC(=O)C)OC(=O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C12H16O7
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

2873-29-2
4098-06-0

2.3.2 European Community (EC) Number

2.3.3 DSSTox Substance ID

2.3.4 Nikkaji Number

2.3.5 NSC Number

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol
  • 3,4,6-tri-O-acetyl-D-glucal
  • 3,4,6-tri-O-acetylglucal

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
272.25 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
0.2
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
272.08960285 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
272.08960285 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
88.1 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
388
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
3
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 2019.01.04)

3.2 Experimental Properties

3.2.1 Physical Description

White crystalline powder; [Sigma-Aldrich MSDS]

3.3 Chemical Classes

Biological Agents -> Monosaccharides and Derivatives

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Instrument Name
Bruker AM-270
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
SF = 090 MHz
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 3
View All
NIST Number
13212
Library
Main library
Total Peaks
21
m/z Top Peak
97
m/z 2nd Highest
110
m/z 3rd Highest
139
Thumbnail
Thumbnail
2 of 3
View All
Source of Spectrum
SRH-2022-2977-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2.2 Other MS

Authors
SASAKI S, TOYOHASHI UNIV. OF TECH.
Instrument
Unknown
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Top 5 Peaks

110 999

97 990

139 900

81 400

152 360

Thumbnail
Thumbnail
License
CC BY-NC-SA

6 Chemical Vendors

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P317, P330, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

7.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)
Not Classified

7.1.3 Hazards Summary

Not considered hazardous by GHS classification; [Sigma-Aldrich MSDS] See beta-D-Glucose and Glucose.

7.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-, triacetate: Does not have an individual approval but may be used under an appropriate group standard
New Zealand EPA Inventory of Chemical Status
2,6-Anhydro-5-deoxy-D-arabino-hex-5-enitol triacetate: Does not have an individual approval but may be used under an appropriate group standard

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Thieme References

8.4 Chemical Co-Occurrences in Literature

8.5 Chemical-Gene Co-Occurrences in Literature

8.6 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

9.3 Chemical Co-Occurrences in Patents

9.4 Chemical-Disease Co-Occurrences in Patents

9.5 Chemical-Gene Co-Occurrences in Patents

10 Biological Test Results

10.1 BioAssay Results

11 Classification

11.1 MeSH Tree

11.2 ChemIDplus

11.3 UN GHS Classification

11.4 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. 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
    2,6-anhydro-5-deoxy-D-arabino-hex-5-enitol triacetate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.021.690
    1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol triacetate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.018.827
    1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol triacetate (EC: 220-709-0)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/96661
    2,6-anhydro-5-deoxy-D-arabino-hex-5-enitol triacetate (EC: 223-859-5)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/70577
  3. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  4. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. EPA DSSTox
    1,3,4-Tri-O-acetyl-2,6-anhydro-5-deoxyhex-5-enitol
    https://comptox.epa.gov/dashboard/DTXSID90863045
  6. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  7. Japan Chemical Substance Dictionary (Nikkaji)
  8. MassBank Europe
  9. 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
  10. SpectraBase
    D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-, triacetate
    https://spectrabase.com/spectrum/1wk3E8pktE
    3,4,6-Tri-O-acetyl-1,2-dideoxy-glucohex-1-enopyranose
    https://spectrabase.com/spectrum/5xgnZSKePLT
    3,4,6-Tri-O-acetyl-1,2-dideoxy-glucohex-1-enopyranose
    https://spectrabase.com/spectrum/GgsGRcbXse1
  11. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  12. PubChem
  13. 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
  14. GHS Classification (UNECE)
  15. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  16. PATENTSCOPE (WIPO)
CONTENTS