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Methyl 2-nonynoate

PubChem CID
8137
Structure
Methyl 2-nonynoate_small.png
Methyl 2-nonynoate_3D_Structure.png
Molecular Formula
Synonyms
  • Methyl 2-nonynoate
  • Methyl non-2-ynoate
  • 111-80-8
  • Methyl octine carbonate
  • 2-Nonynoic acid methyl ester
Molecular Weight
168.23 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
Methyl non-2-ynoate is a ynoate ester.
Methyl 2-nonynoate has been reported in Artemisia annua with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Methyl 2-nonynoate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl non-2-ynoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H16O2/c1-3-4-5-6-7-8-9-10(11)12-2/h3-7H2,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CCCCCCC#CC(=O)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H16O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

111-80-8

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 FEMA Number

2.3.8 HMDB ID

2.3.9 JECFA Number

1356

2.3.10 Lipid Maps ID (LM_ID)

2.3.11 Metabolomics Workbench ID

2.3.12 Nikkaji Number

2.3.13 NSC Number

2.3.14 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-nonynoic acid methyl ester
  • methyl 2-nonynoate
  • methyl octine carbonate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
168.23 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.7
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
2
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
168.115029749 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
168.115029749 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
26.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
183
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

Liquid
Colourless oily liquid; Peach, violet aroma

3.2.2 Boiling Point

121.00 to 122.00 °C. @ 20.00 mm Hg
The Good Scents Company Information System

3.2.3 Solubility

Soluble in oils; Insoluble in water
Soluble (in ethanol)

3.2.4 Density

0.913-0.916

3.2.5 Refractive Index

1.445-1.451

3.2.6 Kovats Retention Index

Semi-standard non-polar
1310 , 1310 , 1311 , 1311 , 1312 , 1321

3.3 Chemical Classes

3.3.1 Food Additives

FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

3.3.2 Fragrances

Fragrance Ingredient (Methyl 2-nonynoate) -> IFRA transparency List
Fragrance substance (Methyl octine carbonate) -> IFRA amendment 49

3.3.3 Lipids

Fatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
Givaudan-Delawanna, Inc., New York, New York
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
276693
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bruker WH-90
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
237564
Library
Main library
Total Peaks
132
m/z Top Peak
79
m/z 2nd Highest
43
m/z 3rd Highest
41
Thumbnail
Thumbnail
2 of 5
View All
NIST Number
35957
Library
Replicate library
Total Peaks
87
m/z Top Peak
41
m/z 2nd Highest
79
m/z 3rd Highest
43
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4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
CAPILLARY CELL: NEAT
Source of Sample
Givaudan Corporation, New York, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
CAPILLARY CELL: NEAT
Source of Sample
Givaudan-Delawanna, Inc., New York, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
276693
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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4.3.3 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Vapor Phase
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
276693
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 FEMA Flavor Profile

Green

7.3 FDA Substances Added to Food

Used for (Technical Effect)
FLAVORING AGENT OR ADJUVANT
Document Number (21 eCFR)
FEMA Number
2726
GRAS Number
3, 25
JECFA Flavor Number
1356

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

1 of 2
Chemical Name
METHYL 2-NONYNOATE
Evaluation Year
2004
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph
2 of 2
Chemical Name
METHYL OCTINE CARBONATE
Evaluation Year
2004
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Extracellular
  • Membrane

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

9.1.1 Use Classification

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

9.1.2 Household Products

Household & Commercial/Institutional Products

Information on 16 consumer products that contain Methyl Octine Carbonate in the following categories is provided:

• Auto Products

• Inside the Home

9.2 IFRA Fragrance Standards

IFRA Substance
Methyl octine carbonate
Synonyms
Methyl octyne carbonate; Methyl 2-nonynoate; 2-Nonynoic acid, methyl ester; MOC
Amendment
49
IFRA Standard type
Restriction: This material should be used only in the limited quantity as stated in the Standard
Intrinsic property driving the risk management measure
DERMAL SENSITIZATION
Flavor use consideration
Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.
Restricted ingredients: notes
When used in the same fragrance compound within a specific QRA category, the sum total of and Methyl heptine carbonate (MHC, CAS number 111-12-6) and Methyl octine carbonate (MOC, CAS number 111-80-8) contributions must not exceed the maximum permitted level for MHC. At the same time, the contribution from MOC should always respect the maximum levels permitted as listed in the table above.

9.2.1 Restriction Limits in the Finished Product (%)

Category 1 (%)
0.0018 [Products applied to the lips]
Category 2 (%)
0.00055 [Products applied to the axillae]
Category 3 (%)
0.011 [Products applied to the face/body using fingertips]
Category 4 (%)
0.01 [Products related to fine fragrances]
Category 5A (%)
0.0026 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]
Category 5B (%)
0.0026 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]
Category 5C (%)
0.0026 [Products applied to the hands using the hands (palms), primarily leave-on (Hand cream)]
Category 5D (%)
0.0026 [Products applied to babies using the hands (palms), primarily leave-on (Baby cream, oil, talc)]
Category 6 (%)
0.0061 [Products with oral and lip exposure]
Category 7A (%)
0.021 [Rinse-off products applied to the hair with some hand contact]
Category 7B (%)
0.021 [Leave-on products applied to the hair with some hand contact]
Category 8 (%)
0.0011 [Products with significant anogenital exposure (tampon)]
Category 9 (%)
0.02 [Products with body and hand exposure, primarily rinse off]
Category 10A (%)
0.072 [Household care products with mostly hand contact (excluding aerosol/spray products)]
Category 10B (%)
0.072 [Household care products with mostly hand contact (household aerosol/spray products)]
Category 11A (%)
0.04 [Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure]
Category 11B (%)
0.04 [Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure]
Category 12 (%)
No Restriction [Other air care products not intended for direct skin contact, minimal or insignificant transfer to skin]

9.3 General Manufacturing Information

EPA TSCA Commercial Activity Status
2-Nonynoic acid, methyl ester: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H302 (99.6%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (74.9%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (97.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H400 (75%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H412 (75%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P332+P317, P333+P317, P362+P364, P391, 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 1826 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

Acute Tox. 4 (99.6%)

Skin Irrit. 2 (74.9%)

Skin Sens. 1A (97.9%)

Aquatic Acute 1 (75%)

Aquatic Chronic 3 (75%)

Skin sensitisation - category 1A

10.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 2-Nonynoic acid, methyl ester
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Methyl 2-nonynoate: Does not have an individual approval but may be used under an appropriate group standard

10.3 Other Safety Information

Chemical Assessment
Evaluation - Octynoic and nonynoic acid esters

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Nature Journal References

13.6 Chemical Co-Occurrences in Literature

13.7 Chemical-Gene Co-Occurrences in Literature

13.8 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

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

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 LIPID MAPS Classification

18.4 ChemIDplus

18.5 UN GHS Classification

18.6 EPA CPDat Classification

18.7 NORMAN Suspect List Exchange Classification

18.8 EPA DSSTox Classification

18.9 Consumer Product Information Database Classification

18.10 EPA TSCA and CDR Classification

18.11 LOTUS Tree

18.12 EPA Substance Registry Services Tree

18.13 MolGenie Organic Chemistry Ontology

19 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/
  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 Chemicals under the TSCA
    2-Nonynoic acid, methyl ester
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. 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
  8. 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
  9. 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
  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. ChEBI
  13. 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/
  14. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  15. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  16. 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/
  17. EPA Chemical and Products Database (CPDat)
  18. EU Food Improvement Agents
  19. 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
  20. Hazardous Chemical Information System (HCIS), Safe Work Australia
  21. FDA Substances Added to Food
    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
  22. Flavor and Extract Manufacturers Association (FEMA)
  23. Japan Chemical Substance Dictionary (Nikkaji)
  24. KNApSAcK Species-Metabolite Database
  25. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  26. Metabolomics Workbench
  27. Nature Chemistry
  28. 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-Nonynoic acid, methyl ester
    http://www.nist.gov/srd/nist1a.cfm
  29. SpectraBase
  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. PubChem
  34. 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
    2-nonynoic acid methyl ester
    https://www.ncbi.nlm.nih.gov/mesh/67055802
  35. GHS Classification (UNECE)
  36. 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/
  37. EPA Substance Registry Services
  38. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  39. PATENTSCOPE (WIPO)
CONTENTS