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Tricyclene

PubChem CID
79035
Structure
Tricyclene_small.png
Tricyclene_3D_Structure.png
Molecular Formula
Synonyms
  • Tricyclene
  • 508-32-7
  • cyclene
  • 1,7,7-Trimethyltricyclo[2.2.1.02,6]heptane
  • Tricyclene (VAN)
Molecular Weight
136.23 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2024-12-07
Description
Tricyclene is a monoterpene that is tricyclo[2.2.1.0(2,6)]heptane bearing a three additional methyl substituents (one at position 1 and two at position 7).
Tricyclene has been reported in Artemisia thuscula, Helichrysum taenari, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Tricyclene.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,7,7-trimethyltricyclo[2.2.1.02,6]heptane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H16/c1-9(2)6-4-7-8(5-6)10(7,9)3/h6-8H,4-5H2,1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RRBYUSWBLVXTQN-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1(C2CC3C1(C3C2)C)C
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C10H16
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

20347-59-5, 22273-90-1

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Lipid Maps ID (LM_ID)

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 NSC Number

2.3.13 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
136.23 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.2
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
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
136.125200510 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
136.125200510 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
0Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
190
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
2
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)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Boiling Point

152.00 to 153.00 °C. @ 760.00 mm Hg
The Good Scents Company Information System

3.2.3 Melting Point

67 - 68 °C

3.2.4 Kovats Retention Index

Standard non-polar
922, 918, 919, 924, 921, 923, 922, 927, 922, 920, 915, 921, 917, 906, 925, 916, 899, 921, 926, 921, 920, 922, 923, 920.4, 922, 922, 925, 928, 915, 920, 922, 923, 915, 920, 942, 928.5, 921, 915, 906, 934, 921, 921, 915, 918, 901, 927, 917, 920, 927, 916, 921, 923, 927, 927, 921, 921, 921, 916, 906, 916, 924, 927, 926, 911, 928, 909, 926, 908, 923, 911, 908, 921, 920, 909, 921, 917, 935, 934, 923.9, 925.6, 921, 920, 932, 915, 918, 917, 908, 926, 926, 918, 919, 921, 933, 921, 921, 922, 921, 921, 949.7, 940, 921, 922, 919, 936, 936, 921, 918, 921, 919, 922.8
Semi-standard non-polar
931, 923, 926, 926, 928, 919, 934, 920, 926, 926, 900, 927, 927, 927, 919, 917, 924, 923, 927, 913, 923, 928, 928, 926, 925, 919, 921, 925, 924, 928, 925, 921, 926, 928, 923, 924, 924, 913, 924, 925, 928, 920, 923, 926, 921, 925, 913, 912, 920, 922, 926, 928, 927, 926, 928, 927, 927, 926, 927, 914, 931, 940, 930.3, 926, 924, 924, 928, 926, 926, 926, 926, 926, 926, 926, 926, 940, 963, 936.6, 921, 924, 927, 928, 927, 926, 921, 930, 924, 929, 915, 924, 921, 923, 927, 923, 924, 927, 922, 930, 924, 930, 923, 925, 926, 924, 921, 922, 920, 926, 928, 920, 931, 901, 926, 895, 919, 905, 922, 920, 927, 905, 931, 895, 921, 925, 906, 927, 920, 925, 913, 924, 927, 920, 922, 926, 925, 929, 925, 918, 926, 926, 915, 905, 926, 907, 923, 924, 927, 911, 921, 927, 918, 928, 922, 926, 926, 919, 919, 906, 927, 927, 926, 928, 922, 928, 904, 907, 927, 926, 926, 922, 923, 925, 902, 908, 927, 930, 929, 927, 925, 923, 921, 929, 929, 926, 926, 928, 926, 905, 925, 923, 927, 917, 927, 921, 938, 920, 926, 924, 921, 920, 921, 928, 925, 911, 920, 927, 925, 931, 927, 926, 924, 925, 918, 927, 927, 926, 926, 926, 934, 920
Standard polar
998, 1013, 1000, 1007, 1029, 1030, 1022, 1047, 998, 1007, 1008, 993, 1012, 1021, 1005, 1022, 1008, 1015, 1020, 1002, 1015, 1007, 1003, 1028, 1009.5, 1014, 1018, 1011, 1016, 1014, 1002, 1005, 1014, 1015, 1007, 1019, 1021, 1030, 1020, 1001, 1030, 1014, 1014, 1014, 1009, 1010, 1014, 1014, 1002, 1014, 1014, 1008, 995, 1014, 1014, 1017, 1010, 1014, 1014, 1014, 1014, 1014, 1014, 1029, 1014, 1014, 1014, 1014, 1005, 1003, 1009, 1014, 1013, 1015, 1017, 1020, 1004, 1004, 1020

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Lipids

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 6
View All
NIST Number
118905
Library
Main library
Total Peaks
79
m/z Top Peak
93
m/z 2nd Highest
91
m/z 3rd Highest
92
Thumbnail
Thumbnail
2 of 6
View All
NIST Number
249442
Library
Replicate library
Total Peaks
70
m/z Top Peak
93
m/z 2nd Highest
41
m/z 3rd Highest
39
Thumbnail
Thumbnail

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

Membrane

8.2 Biochemical Reactions

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Tricyclo[2.2.1.02,6]heptane, 1,7,7-trimethyl-: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 74.2% (89 of 120) of all reports. Pictograms displayed are for 25.8% (31 of 120) of reports that indicate hazard statements.
Pictogram(s)
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H304 (15%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

H400 (10.8%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (10.8%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P273, P301+P316, P331, P391, P405, and P501

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

ECHA C&L Notifications Summary

Aggregated GHS information provided per 120 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 89 of 120 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 2 notifications provided by 31 of 120 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Asp. Tox. 1 (15%)

Aquatic Acute 1 (10.8%)

Aquatic Chronic 1 (10.8%)

10.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Tricyclo2.2.1.02,6heptane, 1,7,7-trimethyl-: Does not have an individual approval but may be used under an appropriate group standard

11 Literature

11.1 Consolidated References

11.2 Springer Nature References

11.3 Chemical Co-Occurrences in Literature

11.4 Chemical-Gene Co-Occurrences in Literature

11.5 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Pathways

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

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

16 Classification

16.1 ChEBI Ontology

16.2 LIPID MAPS Classification

16.3 KEGG: Lipid

16.4 ChemIDplus

16.5 UN GHS Classification

16.6 EPA CPDat Classification

16.7 NORMAN Suspect List Exchange Classification

16.8 EPA DSSTox Classification

16.9 EPA TSCA and CDR Classification

16.10 LOTUS Tree

16.11 EPA Substance Registry Services Tree

16.12 MolGenie Organic Chemistry Ontology

17 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. 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
  4. EPA Chemicals under the TSCA
    Tricyclo[2.2.1.02,6]heptane, 1,7,7-trimethyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    1,7,7-Trimethyltricyclo[2.2.1.02,6]heptane
    https://comptox.epa.gov/dashboard/DTXSID90858714
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  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. 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
  8. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    1,7,7-Trimethyltricyclo[2.2.1.02,6]heptane
    http://www.hmdb.ca/metabolites/HMDB0038121
  9. 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/
  10. ChEBI
  11. 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/
  12. EPA Chemical and Products Database (CPDat)
    1,7,7-Trimethyltricyclo[2.2.1.02,6]heptane
    https://comptox.epa.gov/dashboard/DTXSID90858714#exposure
  13. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
    1,7,7-Trimethyltricyclo[2.2.1.02,6]heptane
    https://foodb.ca/compounds/FDB017346
  14. Japan Chemical Substance Dictionary (Nikkaji)
  15. 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
  16. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  17. Natural Product Activity and Species Source (NPASS)
  18. Metabolomics Workbench
  19. 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
    Tricyclo[2.2.1.0(2,6)]heptane, 1,7,7-trimethyl-
    http://www.nist.gov/srd/nist1a.cfm
  20. SpectraBase
    Tricyclo[2.2.1.02,6]heptane, 1,7,7-trimethyl-
    https://spectrabase.com/spectrum/FQ6ZQcoTwC6
    Tricyclo[2.2.1.02,6]heptane, 1,7,7-trimethyl-
    https://spectrabase.com/spectrum/EWsswldj5kq
  21. 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
  22. Springer Nature
  23. SpringerMaterials
  24. Wikidata
  25. PubChem
  26. GHS Classification (UNECE)
  27. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  28. EPA Substance Registry Services
  29. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  30. PATENTSCOPE (WIPO)
CONTENTS