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myxoxanthophyll
Sign in to saveMyxoxanthophyll is a carotenoid glycoside pigment present (usually as rhamnosides) in the photosynthetic apparatus of cyanobacteria. It is named after the word "Myxophyceae", a former term for cyanobacteria. As a monocyclic xanthophyll, it has a yellowish color. It is required for normal cell wall structure and thylakoid organization in the cyanobacterium Synechocystis. The pigment is unusual because it is glycosylated on the 2'-OH rather than the 1'-OH position of the molecule. Myxoxanthophyll was first isolated from Oscillatoria rubenscens in 1936.
Chemical data
- Formula
- C46H66O8
- Molecular weight
- 747 g/mol
- IUPAC name
- (3R,4S,5S,6R)-2-[(3R,4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E)-2-hydroxy-25-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-2,6,10,14,19,23-hexamethylpentacosa-4,6,8,10,12,14,16,18,20,22,24-undecaen-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
- SMILES
- CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H](C(C)(C)O)OC2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)/C)/C
- InChIKey
- VJHXSZGYVIKVEU-SKFWZKHZSA-N
- XLogP
- 9.1
- Polar surface area
- 140 Ų
- H-bond donors
- 6
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 746.475769
Show 4 more facts
- canonical SMILES
- CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC=C(C)C=CC(C(C)(C)O)OC2C(C(C(C(O2)CO)O)O)O)C)C
- chemical formula
- C₄₆H₆₆O₈
- isomeric SMILES
- CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H](C(C)(C)O)OC2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)/C)/C
- Commons category
- Myxoxanthophyll
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- References
- External links
Myxoxanthophyll is a carotenoid glycoside pigment present (usually as rhamnosides) in the photosynthetic apparatus of cyanobacteria. It is named after the word "Myxophyceae", a former term for cyanobacteria. As a monocyclic xanthophyll, it has a yellowish color. It is required for normal cell wall structure and thylakoid organization in the cyanobacterium Synechocystis. The pigment is unusual because it is glycosylated on the 2'-OH rather than the 1'-OH position of the molecule. Myxoxanthophyll was first isolated from Oscillatoria rubenscens in 1936.
== Synthesis == The bright red pigment lycopene is the acyclic precursor of all carotenoids in cyanobacteria. In myxoxanthophyll synthesis, lycopene is enzymatically converted to 1-hydroxylycoprene, then to intermediates 1'-hydroxy-y-carotene, plectaniaxanthin, and myxol. Finally, the hydroxyl group in myxol is glycosylated at the 2' position to form myxoxanthophyll.
Excerpted from Wikipedia’s “myxoxanthophyll” article, available under the CC BY-SA 4.0 licence.