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Lauryl glycidyl ether

PubChem CID
17163
Structure
Lauryl glycidyl ether_small.png
Lauryl glycidyl ether_3D_Structure.png
Molecular Formula
Synonyms
  • Lauryl glycidyl ether
  • 2461-18-9
  • DODECYL GLYCIDYL ETHER
  • Glycidyl Lauryl Ether
  • 2-(dodecoxymethyl)oxirane
Molecular Weight
242.40 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-11
Description
Lauryl glycidyl ether is a clear colorless viscous liquid. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Lauryl glycidyl ether.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(dodecoxymethyl)oxirane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-16-13-15-14-17-15/h15H,2-14H2,1H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CCCCCCCCCCCCOCC1CO1
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H30O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2461-18-9

2.3.2 Deprecated CAS

136959-08-5, 60616-93-5
60616-93-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1-dodecyl glycidyl ether
  • C12Ge cpd

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
242.40 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
5.4
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
13
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
242.224580195 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
242.224580195 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
21.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
17
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
159
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
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

Lauryl glycidyl ether is a clear colorless viscous liquid. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Clear, colorless viscous liquid; [CAMEO]

3.2.2 Solubility

less than 1 mg/mL at 66 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

3.3 Chemical Classes

3.3.1 Polymers

Plastics & Rubber -> Glycidyl Ethers

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 4
View All
NIST Number
291547
Library
Main library
Total Peaks
92
m/z Top Peak
57
m/z 2nd Highest
55
m/z 3rd Highest
43
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
69643
Library
Replicate library
Total Peaks
88
m/z Top Peak
57
m/z 2nd Highest
43
m/z 3rd Highest
55
Thumbnail
Thumbnail

6 Chemical Vendors

7 Use and Manufacturing

7.1 Uses

Sources/Uses
Used to make cosmetics, pharmaceuticals, emulsifiers; Also used as a heat stabilizer for polymers and as a reactive diluent for epoxy resins; [HSDB]
Industrial Processes with risk of exposure
PREPARATION OF COSMETICS & PHARMACEUTICALS
VANLERBERGHE G, SEBAG H; NONIONIC SURFACTANTS AND COMPOSITION CONTAINING THEM; FR DEMANDE PATENT NO 2482128 11/13/81 (OREAL SA)
PREPARATION OF WATER-IN-OIL EMULSIFIER
OPPENLAENDER K ET AL; WATER-IN-OIL EMULSIONS; US PATENT NO 4115314 09/19/78 (BASF A-G)
SECONDARY HEAT STABILIZER FOR POLYMERS (EG, PVC)
SRI
REACTIVE DILUENT FOR EPOXY RESINS (AS MIXT)
SRI

7.2 Methods of Manufacturing

CONDENSATION OF DODECANOL WITH EPICHLOROHYDRIN (COMMERCIAL PRODUCT IS A MIXT PRODUCED FROM C12 & C14 ALCOHOLS)
SRI

7.3 U.S. Production

(1979) 4.54X10+8 G (EST; AS MIXTURE)
SRI
(1981) No Data
SRI

7.4 U.S. Imports

(1979) No Data
SRI
(1981) No Data
SRI

7.5 U.S. Exports

(1979) No Data
SRI
(1981) No Data
SRI

7.6 General Manufacturing Information

EPA TSCA Commercial Activity Status
Oxirane, 2-[(dodecyloxy)methyl]-: ACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (22.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H318 (98.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H335 (22.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H413 (98.7%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P333+P317, P362+P364, P403+P233, 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 79 reports by companies from 3 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.

8.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Skin Sens. 1 (22.8%)

Eye Dam. 1 (98.7%)

STOT SE 3 (22.8%)

Aquatic Chronic 4 (98.7%)

8.1.3 Fire Hazards

Flash point data for this compound are not available but it is probably combustible. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

8.1.4 Hazards Summary

An strong irritant; May cause serious eye injury; May cause skin sensitization; [MSDSonline] See GLYCIDYL ETHERS.

8.2 First Aid Measures

8.2.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

8.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

8.4 Handling and Storage

8.4.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

8.5 Exposure Control and Personal Protection

8.5.1 Personal Protective Equipment (PPE)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

8.6 Stability and Reactivity

8.6.1 Air and Water Reactions

Insoluble in water.

8.6.2 Reactive Group

Ethers

Epoxides

8.6.3 Reactivity Profile

LAURYL GLYCIDYL ETHER is a ether-epoxide derivative. The ether being relatively unreactive. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert alcohols to aldehydes or ketones.

8.7 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Oxirane, [(dodecyloxy)methyl]-

9 Toxicity

9.1 Toxicological Information

9.1.1 Adverse Effects

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

9.1.2 Human Toxicity Excerpts

GLYCIDYL ETHERS...CHARACTERISTICALLY...ARE VERY IRRITATING TO THE EYES, SKIN AND RESPIRATORY TRACT. /GLYCIDYL ETHERS/
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 529
EXAMINATION BY UNSCHEDULED DNA SYNTHESIS USING WI38 CELLS SHOWED THAT ALKYL GLYCIDYL ETHERS C-8 OR HIGHER SHOWED VERY WEAK OR NO MUTAGENIC RESPONSES. DODECYL GLYCIDYL ETHER WAS INCLUDED IN THE ASSAY.
THOMPSON ED ET AL; MUTAGENICITY OF ALKYL GLYCIDYL ETHERS IN THREE SHORT-TERM ASSAYS; MUTAT RES 90(3) 213 (1981)

9.1.3 Non-Human Toxicity Excerpts

WHEN EXAMINED IN THE SALMONELLA/MAMMALIAN MICROSOME ASSAY & THE L5178Y MOUSE LYMPHOMA ASSAY, ALKYL GLYCIDYL ETHERS C-8 OR HIGHER SHOWED VERY WEAK OR NO MUTAGENIC RESPONSES. DODECYL GLYCIDYL ETHER WAS INCLUDED IN THE ASSAY.
THOMPSON ED ET AL; MUTAGENICITY OF ALKYL GLYCIDYL ETHERS IN THREE SHORT-TERM ASSAYS; MUTAT RES 90(3) 213 (1981)

10 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Contact dermatitis, allergic [Category: Skin Disease]

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Chemical Co-Occurrences in Literature

11.5 Chemical-Gene 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 Classification

14.1 MeSH Tree

14.2 ChemIDplus

14.3 CAMEO Chemicals

14.4 UN GHS Classification

14.5 NORMAN Suspect List Exchange Classification

14.6 EPA DSSTox Classification

14.7 EPA TSCA and CDR Classification

14.8 EPA Substance Registry Services Tree

14.9 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. 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/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. EPA Chemicals under the TSCA
    Oxirane, 2-[(dodecyloxy)methyl]-
    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. Hazardous Substances Data Bank (HSDB)
  10. 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
    Dodecyl glycidyl ether
    https://haz-map.com/Agents/5055
  11. 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
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. 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, [(dodecyloxy)methyl]-
    http://www.nist.gov/srd/nist1a.cfm
  14. SpectraBase
    Oxirane, [(dodecyloxy)methyl]-
    https://spectrabase.com/spectrum/HjAx46O4XpM
  15. Springer Nature
  16. Wikidata
  17. PubChem
  18. 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
  19. GHS Classification (UNECE)
  20. 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/
  21. EPA Substance Registry Services
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  23. PATENTSCOPE (WIPO)
CONTENTS