| Identification | More | [Name]
3'-(Acetyloxy)-6',7'-didehydro-5,6-epoxy-5,5',6,6',7,8-hexahydro-3,5'-dihydroxy-8-oxo-beta,beta-carotene | [CAS]
3351-86-8 | [Synonyms]
3'-(acetyloxy)-6',7'-didehydro-5,6-epoxy-5,5',6,6',7,8-hexahydro-3,5'-dihydroxy-8-oxo-beta,beta-carotene
FUCOXANTHIN
(3s,3’s,5r,5’r,6s,6’r)-hydro-5’-dihydroxy-8-oxo-
beta,beta-carotene,3’-(acetyloxy)-6’,7’-didehydro-5,6-epoxy-5,5’,6,6’,7,8-hexa
3'-(Acetyloxy)-6',7'-didehydro-5,6-epoxy-5,5',6,6',7,8-hexahydro-3,5'-dihydroxy-8-oxo-beta,beta-carotene
(3S,3'S,5R,5'R,6S,6'R)-6',7'-Didehydro-5,6-epoxy-4',5',6,7-tetrahydro-3,3',5'-trihydroxy-,-caroten-8(5H)-one
all-trans-Fucoxanthin | [EINECS(EC#)]
200-486-6 | [Molecular Formula]
C42H58O6 | [MDL Number]
MFCD01745140 | [Molecular Weight]
658.91 | [MOL File]
3351-86-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
166-168°C | [alpha ]
D18 +72.5 ±9° (chloroform) | [Boiling point ]
590.43°C (rough estimate) | [density ]
1.09 | [refractive index ]
n20/D1.360-1.362 | [Fp ]
14℃ | [storage temp. ]
-20°C | [solubility ]
Ethanol, | [form ]
neat | [pka]
14.47±0.60(Predicted) | [color ]
Crystalline | [Usage]
A carotenoid pigment found in fresh brown algae | [λmax]
λ: 444-454 nm Amax | [InChIKey]
SJWWTRQNNRNTPU-WEAAWPSVSA-N | [SMILES]
[C@]12(CC(=O)/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C=C3[C@@](O)(C)C[C@@H](OC(=O)C)CC3(C)C)C(C)(C)C[C@H](O)C[C@]1(O2)C |&1:0,25,29,42,45,r| | [LogP]
7.830 (est) | [CAS DataBase Reference]
3351-86-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Fucoxanthin is a carotenoid that occurs naturally in certain algae. It significantly reduces abdominal white adipose tissue (WAT) in mice and rats when included in their diet.1 Fucoxanthin increases the amount of mitochondrial uncoupling protein 1 (UCP1), a fatty acid-stimulated protein involved in respiration and thermogenesis in WAT of mice and rats.1 In KK-Ay mice, which are used to model obese type 2 diabetics with hyperinsulinemia, fucoxanthin reduces WAT gain and also decreases blood glucose and plasma insulin levels.1,2 | [Chemical Properties]
Crystalline Solid | [Occurrence]
Fucoxanthin is a xanthophyll carotenoid abundant in macroalgae, such as brown seaweeds and microalgae. Several edible brown algae, including Sargassam fusiforme, Laminaria japonica, Undaria pinnatifida, and Padina tetrastromatica, are consumed in Southeast Asia and Europe. The brown algae are good sources of fucoxanthin. However, diatoms, such as Phaeodactylum tricornutum, are preferred sources of fucoxanthin in the food industry because of their higher fucoxanthin content and extraction efficiency with shorter growth cycles than those of macroalgae[1].
| [Uses]
Fucoxanthin has been used to study its neuroprotective effects. It has also been used in calibration to identify the most efficient fucoxanthin producing strains of microalgae. | [Uses]
Fucoxanthin is a carotenoid pigment found in fresh brown algae.It can be used as an anti-obesity, anticancer, anti-cholesterol, and anti-diabetic agent and as a food colorant, but it is very unstable. It is easily affected by heating, aerial exposure, and illumination. | [Uses]
Fucoxanthin is a carotenoid that occurs naturally in certain algae. It significantly reduces abdominal white adipose tissue (WAT) in mice and rats when included in their diet. Fucoxanthin increases the amount of mitochondrial uncoupling protein 1 (UCP1), a fatty acid-stimulated protein involved in respiration and thermogenesis in WAT of mice and rats. In KK-Ay mice, which are used to model obese type 2 diabetics with hyperinsulinemia, fucoxanthin reduces WAT gain and also decreases blood glucose and plasma insulin levels. | [Definition]
ChEBI: A natural product found in Sporochnus comosus. | [General Description]
Fucoxanthin is isolated from brown algae. It has anti-angiogenic, hepatoprotective,?cardiovascular and cerebrovascular protective properties. Fucoxanthin stimulates G1 cell-cycle arrest and apoptosis in cancer cell lines. | [Biochem/physiol Actions]
Xanthophyll carotenoid pigment extracted from algae. Exhibits anticancer, antioxidant, anti-obesity and anti-inflammatory properties. | [Side effects]
There are some potential dangers associated with taking Fucoxanthin. These include an increased risk of bleeding, liver damage, and allergic reactions. Additionally, it may interact with certain medications, such as blood thinners, and can cause side effects such as nausea, vomiting, and diarrhea.
| [Metabolism]
Fucoxanthin is unstable and can be easily degraded by heating, aerial exposure, or illumination. The primary metabolites of fucoxanthin are fucoxanthinol and amarouciaxanthin A. Fucoxanthin can be hydrolyzed to fucoxanthinol in the gastrointestinal tract and further converted into amarouciaxanthin A in the liver. In animal studies, no toxicity of fucoxanthin was observed [1].
| [storage]
Store at 2-8°C | [References]
[1] Minkyung Bae . “Health benefits of fucoxanthin in the prevention of chronic diseases.” Biochimica et biophysica acta. Molecular and cell biology of lipids 1865 11 (2020): Article 158618.
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