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(9Z,12Z)-Octadeca-9,12-dien-1-ol

PubChem CID
5365682
Structure
(9Z,12Z)-Octadeca-9,12-dien-1-ol_small.png
(9Z,12Z)-Octadeca-9,12-dien-1-ol_3D_Structure.png
Molecular Formula
Synonyms
  • (9Z,12Z)-Octadeca-9,12-dien-1-ol
  • 506-43-4
  • Linoleyl alcohol
  • cis,cis-9,12-Octadecadien-1-ol
  • cis,cis-Octadeca-9,12-dien-1-ol
Molecular Weight
266.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-04
Description
(9Z,12Z)-octadecadien-1-ol is a long chain fatty alcohol that is octadecanol containing two double bonds located at positions 9 and 12 (the 9Z,12Z-geoisomer). It is a long-chain primary fatty alcohol and a fatty alcohol 18:2.
(9Z,12Z)-Octadeca-9,12-dien-1-ol has been reported in Bidens aurea with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(9Z,12Z)-Octadeca-9,12-dien-1-ol.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(9Z,12Z)-octadeca-9,12-dien-1-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C18H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h6-7,9-10,19H,2-5,8,11-18H2,1H3/b7-6-,10-9-
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

JXNPEDYJTDQORS-HZJYTTRNSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCC/C=C\C/C=C\CCCCCCCCO
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H34O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

506-43-4

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 DSSTox Substance ID

2.3.6 Lipid Maps ID (LM_ID)

2.3.7 Metabolomics Workbench ID

2.3.8 Wikidata

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 9,12-octadecadien-1-ol
  • linoleyl alcohol
  • linoleyl alcohol, (E,E)-isomer
  • linoleyl alcohol, (Z,Z)-isomer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
266.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
6.8
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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
14
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
266.260965704 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
266.260965704 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
20.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
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
206
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
2
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
2052

3.3 Chemical Classes

3.3.1 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.3.2 Lipids

Fatty Acyls [FA] -> Fatty alcohols [FA05]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.1.2 13C NMR Spectra

Source of Sample
M. Dymicky, U.S. Dept. of Agriculture, Errc, Philadelphia, Pennsylvania
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 2
NIST Number
236043
Library
Main library
Total Peaks
155
m/z Top Peak
67
m/z 2nd Highest
81
m/z 3rd Highest
82
Thumbnail
Thumbnail
2 of 2
NIST Number
141197
Library
Replicate library
Total Peaks
116
m/z Top Peak
41
m/z 2nd Highest
67
m/z 3rd Highest
55
Thumbnail
Thumbnail

4.2.2 MS-MS

NIST Number
1193311
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
267.2682
Total Peaks
95
m/z Top Peak
97.1
m/z 2nd Highest
95.1
m/z 3rd Highest
109.1
Thumbnail
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4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
CAPILLARY CELL: NEAT
Source of Sample
M. Dymicky, USDA, Eastern Regional Research Center, Philadelphia, Pennsylvania
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

Linoleyl alcohol has known human metabolites that include linoleyl O-glucuronide.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

7.2 Biochemical Reactions

7.3 Transformations

8 Use and Manufacturing

8.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
9,12-Octadecadien-1-ol, (9Z,12Z)-: ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 100% (99 of 99) of all reports. Pictograms displayed are for < 0.1% (0 of 99) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 99 of 99 companies. For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 99 reports by companies from 2 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 99 of 99 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 0 notifications provided by 0 of 99 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

9.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 9,12-Octadecadien-1-ol, (Z,Z)-

9.3 Other Safety Information

Chemical Assessment
IMAP assessments - 9,12-Octadecadien-1-ol, (Z,Z)-: Human health tier I assessment

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Nature Journal References

10.5 Chemical Co-Occurrences in Literature

10.6 Chemical-Gene Co-Occurrences in Literature

10.7 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

12 Taxonomy

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

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 LIPID MAPS Classification

13.4 ChemIDplus

13.5 UN GHS Classification

13.6 NORMAN Suspect List Exchange Classification

13.7 EPA DSSTox Classification

13.8 EPA TSCA and CDR Classification

13.9 LOTUS Tree

13.10 MolGenie Organic Chemistry Ontology

14 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. EPA Chemicals under the TSCA
    9,12-Octadecadien-1-ol, (9Z,12Z)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    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. ChEBI
  9. 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/
    (9Z,12Z)-Octadeca-9,12-dien-1-ol
    https://www.wikidata.org/wiki/Q6554721
  10. KNApSAcK Species-Metabolite Database
  11. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  12. Metabolomics Workbench
  13. Nature Synthesis
  14. 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
    9,12-Octadecadien-1-ol, (Z,Z)-
    http://www.nist.gov/srd/nist1a.cfm
  15. 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/
    linoleyl alcohol
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  16. 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
  17. SpectraBase
    cis,cis-9,12-octadecadien-1-ol
    https://spectrabase.com/spectrum/6c8Jga94sIc
    cis-,cis-9,12-OCTADECADIEN-1-OL
    https://spectrabase.com/spectrum/34t7dlhXYYR
    cis,cis-9,12-OCTADECADIEN-1-OL
    https://spectrabase.com/spectrum/22HMhi5kywU
  18. Springer Nature
  19. Wikidata
  20. Wikipedia
  21. PubChem
  22. 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
  23. GHS Classification (UNECE)
  24. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  25. PATENTSCOPE (WIPO)
CONTENTS