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Delta-Tocopherol

PubChem CID
92094
Structure
Delta-Tocopherol_small.png
Delta-Tocopherol_3D_Structure.png
Molecular Formula
Synonyms
  • delta-Tocopherol
  • 119-13-1
  • (+)-delta-Tocopherol
  • D-delta-TOCOPHEROL
  • 8-Methyltocol
Molecular Weight
402.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2024-12-28
Description
Delta-tocopherol is a tocopherol in which the chroman-6-ol core is substituted by a methyl group at position 8. It is found particularly in maize (corn) oil and soya bean (soybean) oils. It has a role as a plant metabolite and a food antioxidant. It is a vitamin E and a tocopherol.
delta-Tocopherol has been reported in Guarea kunthiana, Glycine max, and other organisms with data available.
Delta-Tocopherol is the orally bioavailable delta form of the naturally-occurring fat-soluble vitamin E, mostly found in soybean and corn oils, with potential antioxidant activity. Although the exact mechanism of action of this tocopherol has yet to be fully identified, delta-tocopherol appears to have the ability to scavenge free radicals, thereby protecting cells against oxidative damage.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Delta-Tocopherol.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GZIFEOYASATJEH-VHFRWLAGSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=CC(=CC2=C1O[C@](CC2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)O
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C27H46O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

119-13-1

2.3.2 Deprecated CAS

16698-36-5, 37816-35-6, 78656-14-1
16698-36-5, 2914217-06-2, 37816-35-6, 78656-14-1
16698-36-5, 78656-14-1

2.3.3 European Community (EC) Number

204-299-0

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Lipid Maps ID (LM_ID)

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

delta-tocopherol

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
402.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
10
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
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
402.349780706 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
402.349780706 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
29.5Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
29
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
448
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
3
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

Clear, viscous, pale yellowish or orange oil which oxidises and darkens on exposure to air or light
Solid

3.2.2 Melting Point

< 25 °C

3.2.3 Refractive Index

[n]D/20 1,500-1,504

3.2.4 Kovats Retention Index

Standard non-polar
2889

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

Lipids -> Prenol Lipids [PR] -> Quinones and hydroquinones [PR02] -> Vitamin E [PR0202]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Copyright
Database Compilation Copyright © 2021-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

Copyright
Database Compilation Copyright © 2021-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 4
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

208.0 1

209.0 0.93

474.0 0.54

210.0 0.46

249.0 0.34

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2 of 4
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MS Category
Experimental
MS Type
GC-MS
Instrument Type
GC-MS
Top 5 Peaks

208.0 1

209.0 0.93

474.0 0.54

210.0 0.46

249.0 0.34

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4.2.2 MS-MS

1 of 2
Spectra ID
Instrument Type
EI-EBEB (JMS-HX/HX 110A, JEOL)
Ionization Mode
Positive
Top 5 Peaks

402.4948 1

137.0109 0.88

177.0715 0.32

136.0032 0.22

42.9985 0.10

Thumbnail
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2 of 2
NIST Number
1053645
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
403.3571
Total Peaks
72
m/z Top Peak
177
m/z 2nd Highest
178
m/z 3rd Highest
403.3
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4.2.3 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Instrument Type
Quattro_QQQ
Ionization Mode
positive
Top 5 Peaks

403.0 100

136.0 45.91

402.0 43.56

137.0 27.81

70.0 11.05

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Instrument Type
Quattro_QQQ
Ionization Mode
positive
Top 5 Peaks

136.0 100

137.0 47.31

80.0 7.09

109.0 4.95

108.0 4.68

Thumbnail
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4.2.4 Other MS

1 of 4
View All
Authors
Akimoto N, Graduate School of Pharmaceutical Sciences, Kyoto University and Maoka T, Research Institute for Production Development
Instrument
JMS-HX/HX 110A, JEOL
Instrument Type
EI-EBEB
MS Level
MS
Ionization Mode
POSITIVE
Ionization
EI
Top 5 Peaks

402.4948 999

137.0109 876

177.0715 315

136.0032 222

42.9985 101

Thumbnail
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License
CC BY-SA
2 of 4
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
403.58
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
positive
Collision Energy
10
Top 5 Peaks

403 100

404 52.91

387 22.93

386 7.61

405 5.17

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4.3 UV Spectra

Maximum absorptions in absolute ethanol at about 298 nm and 257 nm

4.4 IR Spectra

4.4.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Supelco, Sigma-Aldrich Inc.
Catalog Number
47784
Lot Number
LB63344
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Clinical Trials

7.1.1 EU Clinical Trials Register

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Tissue Locations

  • Adipose Tissue
  • Epidermis
  • Liver
  • Neuron
  • Platelet
  • Prostate
  • Skeletal Muscle

8.1.2 Cellular Locations

  • Extracellular
  • Membrane

8.2 Biochemical Reactions

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants
Safer Chemical Classes -> Green circle Green circle - The chemical has been verified to be of low concern
Food additives

9.1.2 Household Products

Household & Commercial/Institutional Products

Information on 1 consumer products that contain delta-Tocopherol in the following categories is provided:

• Personal Care

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 99.3% (135 of 136) of all reports. Pictograms displayed are for 0.7% (1 of 136) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 135 of 136 companies (only 0.7% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 136 reports by companies from 2 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 135 of 136 reports by companies. For more detailed information, please visit ECHA C&L website.

There is 1 notification provided by 1 of 136 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

Not Classified

10.1.3 EPA Safer Chemical

Chemical: delta-Tocopherol

Green circle Green circle - The chemical has been verified to be of low concern based on experimental and modeled data.

10.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-(4R,8R)-4,8,12-trimethyltridecyl-, (2R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

10.3 Other Safety Information

Chemical Assessment
Evaluation - Tocopherols and their salts and esters

11 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 22148915, 19006102, 23940645, 24424155, 20156336, 19678709, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

14.2 Pathways

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

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

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 LIPID MAPS Classification

17.5 KEGG: Lipid

17.6 EPA Safer Choice

17.7 ChemIDplus

17.8 ChEMBL Target Tree

17.9 UN GHS Classification

17.10 NORMAN Suspect List Exchange Classification

17.11 EPA DSSTox Classification

17.12 Consumer Product Information Database Classification

17.13 EPA TSCA and CDR Classification

17.14 LOTUS Tree

17.15 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-
    https://services.industrialchemicals.gov.au/search-assessments/
    2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-
    https://services.industrialchemicals.gov.au/search-inventory/
  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
    2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-
    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
    [2R[2R*(4R*,8R*)]]-3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
    https://chem.echa.europa.eu/100.003.909
    [2R[2R*(4R*,8R*)]]-3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol (EC: 204-299-0)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/32706
  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
  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/
    2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-(4R,8R)-4,8,12-trimethyltridecyl-, (2R)-
    https://www.epa.govt.nz/industry-areas/hazardous-substances/guidance-for-importers-and-manufacturers/hazardous-substances-databases/
  10. EU Food Improvement Agents
  11. ChEBI
  12. 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/
  13. NCI Thesaurus (NCIt)
    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
  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 Safer Choice
    EPA Safer Chemical Ingredients Classification
    https://www.epa.gov/saferchoice
  18. EU Clinical Trials Register
  19. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  20. SpectraBase
    (R)-2,8-dimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-ol
    https://spectrabase.com/spectrum/B4DDejWnneq
  21. 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
  22. Japan Chemical Substance Dictionary (Nikkaji)
  23. 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
  24. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  25. Natural Product Activity and Species Source (NPASS)
  26. MassBank Europe
  27. Metabolomics Workbench
  28. 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/
  29. 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
  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
  35. GHS Classification (UNECE)
  36. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  37. PATENTSCOPE (WIPO)
CONTENTS