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2,3-Oxidosqualene

PubChem CID
5366020
Structure
2,3-Oxidosqualene_small.png
2,3-Oxidosqualene_3D_Structure.png
Molecular Formula
Synonyms
  • 2,3-Oxidosqualene
  • Squalene oxide
  • 7200-26-2
  • Squalene peroxide
  • 2,3-Edsq
Molecular Weight
426.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-10
Description
2,3-epoxysqualene is a squalene triterpenoid obtained by formal epoxidation across the 2,3 C=C bond of squalene. It is an epoxide and a squalene triterpenoid. It derives from a hydride of a squalene.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2,3-Oxidosqualene.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaenyl]oxirane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

QYIMSPSDBYKPPY-BANQPHDMSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CCC1C(O1)(C)C)/C)/C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C30H50O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 DSSTox Substance ID

2.3.5 Nikkaji Number

2.3.6 Wikidata

2.3.7 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2,3-EDSQ
  • 2,3-epoxy-2,3-dihydrosqualene
  • 2,3-oxidosqualene
  • 2,3-oxidosqualene, (all-E)-(+-)-isomer
  • 2,3-oxidosqualene, (R)-isomer
  • 2,3-oxidosqualene, (R-(all-E))-isomer
  • 2,3-oxidosqualene, (S)-isomer
  • 2,3-oxidosqualene, (S-(all-E))-isomer
  • squalene monohydroperoxide
  • squalene peroxide
  • squalene-2,3-epoxide
  • squalene-2,3-oxide

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
426.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
10.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
15
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
426.386166214 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
426.386166214 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
12.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
31
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
677
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
0
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
4
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)

3.2 Experimental Properties

3.2.1 Kovats Retention Index

Semi-standard non-polar
2963.4

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 4
View All
NIST Number
161611
Library
Main library
Total Peaks
258
m/z Top Peak
69
m/z 2nd Highest
81
m/z 3rd Highest
71
Thumbnail
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2 of 4
View All
NIST Number
412561
Library
Replicate library
Total Peaks
226
m/z Top Peak
69
m/z 2nd Highest
81
m/z 3rd Highest
71
Thumbnail
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6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Springer Nature References

7.4 Thieme References

7.5 Chemical Co-Occurrences in Literature

7.6 Chemical-Gene Co-Occurrences in Literature

7.7 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 WIPO PATENTSCOPE

8.3 Chemical Co-Occurrences in Patents

8.4 Chemical-Disease Co-Occurrences in Patents

8.5 Chemical-Gene Co-Occurrences in Patents

9 Interactions and Pathways

9.1 Pathways

10 Classification

10.1 MeSH Tree

10.2 ChEBI Ontology

10.3 ChemIDplus

10.4 EPA DSSTox Classification

10.5 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    2,2-Dimethyl-3-(3,7,12,16,20-pentamethyl-3,7,11,15,19-heneicosapentaenyl)oxirane
    https://comptox.epa.gov/dashboard/DTXSID50900960
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. ChEBI
  6. Japan Chemical Substance Dictionary (Nikkaji)
  7. 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
    Oxirane, 2,2-dimethyl-3-(3,7,12,16,20-pentamethyl-3,7,11,15,19-heneicosapentaenyl)-, (all-E)-
    http://www.nist.gov/srd/nist1a.cfm
  8. SpectraBase
    OXIRANE, 2,2-DIMETHYL-3-(3,7,12,16,20-PENTAMETHYL-3,7,11,15,19-HENEICOSAPENTAENYL)-, (ALL-E)-
    https://spectrabase.com/spectrum/2OURDPo9Coj
    2,2-Dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethyl-3,7,11,15,19-henicosapentaenyl]oxirane
    https://spectrabase.com/spectrum/4LccW2m8eG
    2,3-EPOXY-2,3-DIHYDRO-SQUALENE
    https://spectrabase.com/spectrum/A20o1z2MojU
  9. Springer Nature
  10. 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/
  11. Wikidata
  12. Wikipedia
  13. PubChem
  14. 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
  15. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  16. PATENTSCOPE (WIPO)
CONTENTS