Violaxanthin
PubChem CID
448438
Structure
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.
Chemical Structure Depiction
(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)
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)
SZCBXWMUOPQSOX-WVJDLNGLSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
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)
C40H56O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 5,6:5',6'-diepoxy-5,5',6,6'- tetrahydro-beta-carotene-3,3'-diol
- violaxanthin
- zeaxanthin diepoxide
- Violaxanthin
- 126-29-4
- all-trans-Violaxanthin
- trans-Violaxanthin
- Zeaxanthin diepoxide
- (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
- UNII-51C926029A
- ALL-E-VIOLAXANTHIN
- VIOLAXANTHIN [MI]
- C ORANGE 15
- ANTI,ANTI-VIOLAXANTHIN
- beta,beta-Carotene-3,3'-diol, 5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6S,6'S)-
- 51C926029A
- VIOLAXANTHIN, ALL-TRANS-
- CHEBI:35288
- E 161e
- VIOLAXANTHIN (E 161E)
- DTXSID901016934
- 5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta-carotene-3,3'-diol
- (3S,3'S,5R,5'R,6S,6'S)-5,5',6,6'-tetrahydro-5,6:5',6'-diepoxy-beta,beta-carotene-3,3'-diol
- (3S,5R,6S,3'S,5'R,6'S)-5,6,5',6'-DIEPOXY-5,6,5',6'- TETRAHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
- 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-beta,beta-carotene-3,3'-diol
- .BETA.-CAROTENE-3,3'-DIOL, 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-
- 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-.BETA.-CAROTENE-3,3'-DIOL
- (3S,3'S,5R,5'R, 6S,6'S)-5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-.BETA.,.BETA.-CAROTENE-3,3'-DIOL
- (3S,3'S,5R,5'R, 6S,6'S)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diol
- (3S,3'S,5R,5'R,6S,6'S)-5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diol
- (3S,5R,6S,3'S,5'R,6'S)-5,6,5',6'-DIEPOXY-5,6,5',6'-TETRAHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
- .BETA.,.BETA.-CAROTENE-3,3'-DIOL, 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-, (3S,3'S,5R,5'R,6S,6'S)-
- (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
- SCHEMBL97720
- CHEBI:27295
- DTXCID001475117
- (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-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
- HY-N9625
- Violaxanthin, >=90.0% (HPLC)
- LMPR01070282
- AKOS040763713
- DB03460
- 1ST159340
- CS-0202315
- NS00070421
- C08614
- Q607883
- 09958A8F-4AFE-43DB-9034-C562F62D8ABD
- BETA-CAROTENE-3,3'-DIOL, 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-
- b,b-Carotene-3,3'-diol,5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6S,6'S)-
Property Name
Property Value
Reference
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)
Solid
208 °C
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C40 isoprenoids (tetraterpenes) [PR0107]
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
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
Accession ID
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
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
Accession ID
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
License
CC BY-SA
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Protein Structures Count
- Extracellular
- Membrane
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=SZCBXWMUOPQSOX-WVJDLNGLSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe 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/
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useViolaxanthinhttps://www.drugbank.ca/drugs/DB03460
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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
- Human Metabolome Database (HMDB)LICENSEHMDB 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/citingViolaxanthinhttp://www.hmdb.ca/metabolites/HMDB0003101
- ChEBIAll-trans-violaxanthinhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:35288
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Violaxanthinhttps://www.wikidata.org/wiki/Q607883LOTUS Treehttps://lotus.naturalproducts.net/
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlPhytochemical compoundshttp://www.genome.jp/kegg-bin/get_htext?br08003.keg
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- Natural Product Activity and Species Source (NPASS)
- MassBank Europe
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Metabolomics Workbench
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://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-olNORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- Protein Data Bank in Europe (PDBe)
- RCSB Protein Data Bank (RCSB PDB)LICENSEData 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
- Rhea - Annotated Reactions DatabaseLICENSERhea 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
- Wikidataviolaxanthinhttps://www.wikidata.org/wiki/Q607883
- WikipediaViolaxanthinhttps://en.wikipedia.org/wiki/Violaxanthin
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.htmlviolaxanthinhttps://www.ncbi.nlm.nih.gov/mesh/67005613
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 397495441https://pubchem.ncbi.nlm.nih.gov/substance/397495441
- NCBI
CONTENTS