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Cyclotene

PubChem CID
6660
Structure
Cyclotene_small.png
Cyclotene_3D_Structure.png
Molecular Formula
Synonyms
  • 80-71-7
  • Cyclotene
  • 2-Hydroxy-3-methylcyclopent-2-enone
  • Methyl cyclopentenolone
  • Corylone
Molecular Weight
112.13 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
Cyclotene has been reported in Capsicum annuum, Picea abies, and other organisms with data available.
Cyclotene is a metabolite found in or produced by Saccharomyces cerevisiae.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cyclotene.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-hydroxy-3-methylcyclopent-2-en-1-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CC1=C(C(=O)CC1)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C6H8O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

80-71-7

2.3.2 Deprecated CAS

765-70-8

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 DSSTox Substance ID

2.3.6 FEMA Number

2.3.7 HMDB ID

2.3.8 JECFA Number

418

2.3.9 Nikkaji Number

2.3.10 NSC Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-hydroxy-1-methylcyclopenten-3-one
  • cyclotene

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
112.13 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
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
112.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
112.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
156
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
0
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

Pellets or Large Crystals; Liquid
white, crystalline powder with a nutty odour, maple-liquorice aroma in dilute solution

3.2.2 Solubility

soluble in alcohol and propylene glycol; slightly soluble in most fixed oils and 1 g in 72 ml water
1 g in 5 ml 90% alcohol (in ethanol)

3.2.3 Dissociation Constants

3.2.4 Kovats Retention Index

Standard non-polar
1000 , 1015 , 1021 , 1025 , 982 , 990 , 995 , 1014 , 1006 , 1006 , 1006 , 1005 , 1001.5 , 1015 , 1021
Semi-standard non-polar
1036 , 1038 , 1028 , 1034 , 1036 , 1037 , 1027 , 1029 , 1022 , 1020.1 , 1026.4 , 1034 , 1042 , 1036 , 1036 , 166.55
Standard polar
1839 , 1833 , 1830 , 1830 , 1824 , 1861 , 1837 , 1829 , 1816 , 1860 , 1839 , 1857 , 1784 , 1806 , 1811 , 1829 , 1829 , 1831 , 1831 , 1834 , 1818 , 1827 , 1832 , 1831 , 1807 , 1835.6 , 1837 , 1799 , 1830 , 1830 , 1809.9 , 1800 , 1830 , 1831 , 1831 , 1831 , 1832 , 1806.4

3.3 Chemical Classes

Other Classes -> Other Organic Compounds

3.3.1 Fragrances

Fragrance Ingredient (Methylcyclopentenolone) -> IFRA transparency List

4 Spectral Information

4.1 1D NMR Spectra

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.
Thumbnail
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2 of 2
Instrument Name
Varian HA-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 5
View All
NIST Number
1673
Library
Main library
Total Peaks
77
m/z Top Peak
112
m/z 2nd Highest
69
m/z 3rd Highest
55
Thumbnail
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2 of 5
View All
NIST Number
156507
Library
Replicate library
Total Peaks
64
m/z Top Peak
112
m/z 2nd Highest
55
m/z 3rd Highest
41
Thumbnail
Thumbnail

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
W270008
Lot Number
05928CE
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
W270008
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

7.2 Associated Foods

7.3 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

1 of 3
Chemical Name
2-HYDROXY-3-METHYL-2-CYCLOPENTEN-1-ONE
Evaluation Year
1998
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph
2 of 3
Chemical Name
CYCLOTENE
Evaluation Year
1998
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph
3 of 3
Chemical Name
MAPLE LACTONE
Evaluation Year
1998
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

8 Use and Manufacturing

8.1 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
Sources/Uses
Active product registrations in the US for use in insect traps; [NPIRS] Product of sugar degradation. [ChemIDplus] Product category is Analytical/Chromatography and Flavors and Fragrances. [Sigma-Aldrich]

8.1.1 Use Classification

Food additives -> Flavoring Agents
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index

8.1.2 Industry Uses

  • Fragrance
  • Flavoring and nutrient

8.1.3 Consumer Uses

Fragrance

8.1.4 Household Products

Household & Commercial/Institutional Products

Information on 5 consumer products that contain 2-Hydroxy-3-methylcyclopent-2-enone in the following categories is provided:

• Auto Products

• Inside the Home

8.2 U.S. Production

Aggregated Product Volume

2019: 15,435 lb

2018: 16,039 lb

2017: 20,407 lb

2016: 17,969 lb

8.3 General Manufacturing Information

Industry Processing Sectors
  • All Other Basic Organic Chemical Manufacturing
  • Food, beverage, and tobacco product manufacturing
EPA TSCA Commercial Activity Status
2-Cyclopenten-1-one, 2-hydroxy-3-methyl-: ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 1571 of 1747 companies

ECHA C&L Notifications Summary

Aggregated GHS information provided per 1747 reports by companies from 8 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 1571 of 1747 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 6 notifications provided by 176 of 1747 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.

9.1.2 Hazard Classes and Categories

Not Classified

9.1.3 Hazards Summary

9.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 2-Cyclopenten-1-one, 2-hydroxy-3-methyl-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Cylcotene: Does not have an individual approval but may be used under an appropriate group standard

10 Toxicity

10.1 Toxicological Information

10.1.1 Acute Effects

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 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 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

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

15 Classification

15.1 MeSH Tree

15.2 ChemIDplus

15.3 UN GHS Classification

15.4 EPA CPDat Classification

15.5 NORMAN Suspect List Exchange Classification

15.6 EPA DSSTox Classification

15.7 Consumer Product Information Database Classification

15.8 EPA TSCA and CDR Classification

15.9 LOTUS Tree

15.10 EPA Substance Registry Services Tree

15.11 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. 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-Hydroxy-3-methyl-2-cyclopenten-1-one
    https://commonchemistry.cas.org/detail?cas_rn=80-71-7
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  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 Chemical Data Reporting (CDR)
    LICENSE
    The U.S. Government retains a nonexclusive, royalty-free license to publish or reproduce these documents, or allow others to do so, for U.S. Government purposes. These documents may be freely distributed and used for non-commercial, scientific and educational purposes.
    https://www.epa.gov/web-policies-and-procedures/epa-disclaimers#copyright
    2-Cyclopenten-1-one, 2-hydroxy-3-methyl-
    https://www.epa.gov/chemical-data-reporting
  6. EPA Chemicals under the TSCA
    2-Cyclopenten-1-one, 2-hydroxy-3-methyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  7. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  8. 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-hydroxy-3-methylcyclopent-2-enone
    https://chem.echa.europa.eu/100.001.186
  9. 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
  10. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  11. 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/
  12. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. 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://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  13. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  14. EPA Chemical and Products Database (CPDat)
  15. 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
  16. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  17. EU Food Improvement Agents
  18. Flavor and Extract Manufacturers Association (FEMA)
  19. 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
    2-Hydroxy-3-methyl-2-cyclopenten-1-one
    https://foodb.ca/compounds/FDB008103
  20. 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
    2-Hydroxy-3-methyl-2-cyclopenten-1-one
    http://www.hmdb.ca/metabolites/HMDB0303163
  21. IUPAC Digitized pKa Dataset
    2-Cyclopenten-1-one, 2-hydroxy-3-methyl-
    https://github.com/IUPAC/Dissociation-Constants
  22. Japan Chemical Substance Dictionary (Nikkaji)
  23. KNApSAcK Species-Metabolite Database
  24. 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/
  25. Natural Product Activity and Species Source (NPASS)
  26. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  27. 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
    2-Cyclopenten-1-one, 2-hydroxy-3-methyl-
    http://www.nist.gov/srd/nist1a.cfm
  28. SpectraBase
    CYCLOPENTEN-3-ON, 2-HYDROXY-1-METHYL-
    https://spectrabase.com/spectrum/AUo0mp7AVlc
    2-Hydroxy-3-methyl-cyclopenten-2-one-1
    https://spectrabase.com/spectrum/3Ml02mLXLgm
    2-Cyclopenten-1-one, 2-hydroxy-3-methyl-
    https://spectrabase.com/spectrum/H6muZRFeBLC
  29. NMRShiftDB
  30. Springer Nature
  31. 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/
  32. Wikidata
  33. Wikipedia
  34. PubChem
  35. 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
  36. GHS Classification (UNECE)
  37. 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/
  38. EPA Substance Registry Services
  39. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  40. PATENTSCOPE (WIPO)
CONTENTS