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Violaxanthin

PubChem CID
448438
Structure
Violaxanthin_small.png
Violaxanthin_3D_Structure.png
Molecular Formula
Synonyms
  • Violaxanthin
  • 126-29-4
  • all-trans-Violaxanthin
  • trans-Violaxanthin
  • Zeaxanthin diepoxide
Molecular Weight
600.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-04
Description
All-trans-violaxanthin is the all-trans-stereoisomer of violaxanthin. It has a role as a food colouring.
Violaxanthin has been reported in Microchloropsis salina, Cladophora glomerata, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Violaxanthin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

SZCBXWMUOPQSOX-WVJDLNGLSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@@]12O[C@@]1(C[C@H](CC2(C)C)O)C)/C)/C)/C=C/C=C(/C=C/[C@@]34O[C@@]3(C[C@H](CC4(C)C)O)C)\C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C40H56O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 DrugBank ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 KEGG ID

2.3.8 Lipid Maps ID (LM_ID)

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5,6:5',6'-diepoxy-5,5',6,6'- tetrahydro-beta-carotene-3,3'-diol
  • violaxanthin
  • zeaxanthin diepoxide

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
600.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
9.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
600.41786026 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
600.41786026 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
65.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
44
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1270
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
6
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
9
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

Solid

3.2.2 Melting Point

208 °C

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.3.2 Lipids

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C40 isoprenoids (tetraterpenes) [PR0107]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 2
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
601
Instrument
Esquire 4000
Instrument Type
QIT
Ionization
ESI
Ionization Mode
positive
Collision Energy
20->10V
Top 5 Peaks

509 100

221 100

565 100

583 100

Thumbnail
Thumbnail
2 of 2
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
601
Instrument
Esquire 4000
Instrument Type
QIT
Ionization
ESI
Ionization Mode
positive
Collision Energy
20->10V
Top 5 Peaks

509 100

221 100

583 100

565 100

Thumbnail
Thumbnail

4.1.2 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
FAB-EBEB
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
FAB
Collision Energy
3 kV
Precursor m/z
600.42
Precursor Adduct
[M]+*
Top 5 Peaks

600.2722 999

42.9754 999

105.0052 631

144.9906 573

118.9931 568

Thumbnail
Thumbnail
License
CC BY-SA
Reference
Akimoto, N.; Takashi, M.; Fujiwara, Y.; Hashimoto, K.; Analysis of carotenoids by FAB CID-MS2 (in Japanese). J. Mass Spectrom. Soc. Jpn. 2000, 48, 32-41. doi:10.5702/massspec.48.32 Maoka, T.; Fujiwara, Y.; Hashimoto, K.; Akimoto, N. Characterization of epoxy carotenoids by fast atom bombardment collision-induced dissociation MS2. Lipids 2004, 39,179-183. doi:10.1007/s11745-004-1217-3
2 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

600 999

221 667

601 445

520 330

352 293

Thumbnail
Thumbnail
License
CC BY-SA

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Human Metabolite Information

7.1.1 Cellular Locations

  • Extracellular
  • Membrane

7.2 Biochemical Reactions

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Chemical Co-Occurrences in Literature

8.4 Chemical-Gene Co-Occurrences in Literature

8.5 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

9.3 Chemical Co-Occurrences in Patents

9.4 Chemical-Disease Co-Occurrences in Patents

9.5 Chemical-Gene Co-Occurrences in Patents

10 Interactions and Pathways

10.1 Protein Bound 3D Structures

10.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

10.2 Pathways

11 Taxonomy

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

12 Classification

12.1 MeSH Tree

12.2 ChEBI Ontology

12.3 LIPID MAPS Classification

12.4 KEGG: Lipid

12.5 KEGG: Phytochemical Compounds

12.6 ChemIDplus

12.7 NORMAN Suspect List Exchange Classification

12.8 EPA DSSTox Classification

12.9 LOTUS Tree

12.10 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. 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. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
  6. 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
  7. ChEBI
  8. 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/
  9. Japan Chemical Substance Dictionary (Nikkaji)
  10. 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
  11. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  12. Natural Product Activity and Species Source (NPASS)
  13. MassBank Europe
  14. 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
  15. Metabolomics Workbench
  16. 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/
    6-(18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl)-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  17. Protein Data Bank in Europe (PDBe)
  18. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  19. 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
  20. Wikidata
  21. Wikipedia
  22. PubChem
  23. 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
  24. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  25. PATENTSCOPE (WIPO)
  26. NCBI
CONTENTS