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Fucoxanthin

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Fucoxanthin
Names
IUPAC name
Acetic acid [(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] ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.212.315 Edit this at Wikidata
  • InChI=1S/C42H60O7/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(49-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42(48)39(8,9)24-34(44)25-41(42,11)47/h12-22,34-35,44,46-48H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23-,34-,35-,40+,41+,42-/m0/s1 checkY
    Key: TZTFIZUHAXDGQM-XJUZQKKNSA-N checkY
  • InChI=1/C42H60O7/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(49-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42(48)39(8,9)24-34(44)25-41(42,11)47/h12-22,34-35,44,46-48H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23-,34-,35-,40+,41+,42-/m0/s1
    Key: TZTFIZUHAXDGQM-XJUZQKKNBK
  • O[C@]2(CC(=O)C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C=C1/C(C)(C)C[C@H](OC(C)=O)C[C@@]1(C)O)[C@](C)(O)C[C@@H](O)CC2(C)C
Properties
C42H58O6
Molar mass 658.920 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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 by various estimates and absorbing significantly in the range of 450 to 540 nm.

Some metabolic and nutritional studies carried out on rats and mice at Hokkaido University indicate that fucoxanthin promotes fat burning within fat cells in white adipose tissue by increasing the expression of thermogenin.[1] There is one known double-blind placebo-controlled human study with fucoxanthin that has been published.[2] The small study in obese women showed in an average 4.9 kg (11 lb) weight loss over a 16-week period[3].

It is non-stimulatory, unlike other compounds such as ephedrine and yohimbine[4].

References

  1. ^ Maeda, H; Hosokawa, M; Sashima, T; Funayama, K; Miyashita, K (2005). "Fucoxanthin from edible seaweed, Undaria pinnatifida, shows antiobesity effect through UCP1 expression in white adipose tissues". Biochemical and biophysical research communications. 332 (2): 392–7. doi:10.1016/j.bbrc.2005.05.002. PMID 15896707.
  2. ^ Abidov, M.; Ramazanov, Z.; Seifulla, R.; Grachev, S. (2010). "The effects of Xanthigen in the weight management of obese premenopausal women with non-alcoholic fatty liver disease and normal liver fat". Diabetes, Obesity and Metabolism. 12: 72. doi:10.1111/j.1463-1326.2009.01132.x.
  3. ^ "Ergo-Log: Fucoxanthin".
  4. ^ "Examine.com - Fucoxanthin".

Other studies

  • Haugan, J (1994). "Isolation and characterisation of four allenic (6'S)-isomers of fucoxanthin". Tetrahedron Letters. 35: 2245. doi:10.1016/S0040-4039(00)76810-9.