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fucoxanthin

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fucoxanthin

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Fucoxanthin is a xanthophyll, with formula C42H58O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510–525 nm and absorbing significantly in the range of 450 to 540 nm.

Chemical data

Formula
C42H58O6
Molecular weight
658.9 g/mol
IUPAC name
[(1S,3R)-3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaenylidene]-3,5,5-trimethylcyclohexyl] acetate
SMILES
C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C(=O)C[C@]12[C@](O1)(C[C@H](CC2(C)C)O)C)/C=C/C=C(\C)/C=C=C3[C@](C[C@H](CC3(C)C)OC(=O)C)(C)O
InChIKey
SJWWTRQNNRNTPU-ABBNZJFMSA-N
XLogP
8.1
Polar surface area
96.4 Ų
H-bond donors
2
H-bond acceptors
6
Formal charge
0

via PubChem

Wikidata facts

Mass
658.423339576
Show 3 more facts
chemical formula
C₄₂H₅₈O₆
isomeric SMILES
CC(=O)O[C@H]1CC(C)(C)C(=C=C\C(=C\C=C\C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C(=O)C[C@@]23O[C@]2(C)C[C@@H](O)CC3(C)C)\C)\C)[C@](C)(O)C1
canonical SMILES
CC(=CC=CC=C(C)C=CC=C(C)C(=O)CC12C(CC(CC1(O2)C)O)(C)C)C=CC=C(C)C=C=C3C(CC(CC3(C)O)OC(=O)C)(C)C
Sources (4)

via Wikidata · CC0

~3 min read

Article

5 sections
Contents
  • Function
  • Sources
  • Bioavailability
  • See also
  • References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 437956950 | ImageFile=Fucoxanthin.svg | ImageSize=350px | IUPACName=(3S,5R,6M,3′S,5′R,6′S)-5′,6′-Epoxy-5,3′-dihydroxy-8′-oxo-6,7-didehydro-5,6,5′,6′,7′,8′-hexahydro-β,β-caroten-3-yl acetate | SystematicName=(1S,3R,4M)-3-Hydroxy-4-{(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-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate | OtherNames= |Section1= |Section2= |Section3= }} Fucoxanthin is a xanthophyll, with formula C42H58O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510–525 nm and absorbing significantly in the range of 450 to 540 nm.

== Function == Carotenoids are pigments produced by plants and algae and play a role in light harvesting as part of the photosynthesis process. Xanthophylls are a subset of carotenoids, identified by the fact that they are oxygenated either as hydroxyl groups or as epoxide bridges. This makes them more water soluble than carotenes such as beta-carotene. Fucoxanthin is a xanthophyll that contributes more than 10% of the estimated total production of carotenoids in nature. It is an accessory pigment found in the chloroplasts of many brown macroalgae, such as Fucus , and the golden-brown unicellular microalgae, the diatoms. It absorbs blue and green light at bandwidth 450–540 nm, imparting a brownish-olive color to algae. Fucoxanthin has a highly unique structure that contains both an epoxide bond and hydroxyl groups along with an allenic bond (two adjacent carbon-carbon double bonds) and a conjugated carbonyl group (carbon-oxygen double bond) in the polyene chain. All of these features provide fucoxanthin with powerful antioxidant activity.

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