3351-86-8

Basic information

• Product Name: Fucoxanthin
• Synonyms: FUCOXANTHIN, CAROTENOID ANTIOXIDANT;(3S,3'S,5R,5'R,6S,6'R,8'R)-3,5,5',6-Tetrahydroxy-8-oxo-6',7'-didehydro-5,5',6,6',7,8-hexahydro-β,β-caroten-3'-yl acetate;(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;FUCOXANTHIN;(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
• CAS NO: 3351-86-8
• Molecular Formula: C₄₂H₅₈O₆
• Molecular Weight: 658.91
• EINECS: 200-486-6
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Herb extract
• Mol File: 3351-86-8.mol

Chemical Properties

• Melting Point: 166-168°C
• Boiling Point: 590.43°C (rough estimate)
• Flash Point: 14℃
• Appearance: Crystalline solid
• Density: 1.09
• Refractive Index: n20/D1.360-1.362
• Storage Temp.: ?20°C
• Solubility: Ethanol,
• PKA: 14.47±0.60(Predicted)
• CAS DataBase Reference: Fucoxanthin(CAS DataBase Reference)
• NIST Chemistry Reference: Fucoxanthin(3351-86-8)
• EPA Substance Registry System: Fucoxanthin(3351-86-8)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16-24/25
• RIDADR: UN1170 - class 3 - PG 2 - Ethanol, solution
• WGK Germany: 3
• Hazardous Substances Data: 3351-86-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Fucoxanthin is used as an anti-obesity, anticancer, anti-cholesterol, and anti-diabetic agent due to its various pharmaceutical effects. It has been shown to possess anti-angiogenic, hepatoprotective, cardiovascular, and cerebrovascular protective properties. It stimulates G1 cell-cycle arrest and apoptosis in cancer cell lines.
Used in Food Industry:
Fucoxanthin is used as a food colorant due to its orange-colored pigment. However, it is important to note that it is very unstable and can be easily affected by heating, aerial exposure, and illumination.
Used in Skin Care and Beauty Industry:
Fucoxanthin is used in the skin care and beauty industry for its anti-inflammatory and anti-oxidant properties, which can contribute to the health and appearance of the skin.
Used in Food Supplements Market:
Fucoxanthin is widely used in the food supplements market for its various health benefits, including its protective effects on nerve cells and its ability to increase the content of arachidonic acid (ARA) and docosahexaenoic acid (DHA) in mice.
Used in Neuroprotective Studies:
Fucoxanthin has been used to study its neuroprotective effects, which can be beneficial for the development of treatments for neurological disorders.
Used in Microalgae Strain Identification:
Fucoxanthin has been used in calibration to identify the most efficient fucoxanthin-producing strains of microalgae, which can be important for optimizing the production of this beneficial compound.

Biochem/physiol Actions

Xanthophyll carotenoid pigment extracted from algae. Exhibits anticancer, antioxidant, anti-obesity and anti-inflammatory properties.

InChI: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

Downstream Products

• 597-43-3 2,2-dimethylsuccinic acid 
• 22451-58-7 3'R,4'-<(2R,4S)-2-hydroxy-4-acetoxy-2,6,6-trimethylcyclohexylidene>but-3'-en-2'-one 
• 3351-87-9 fucoxanthin monoacetate 
• 7176-02-5 fucoxanthinol 
• 7176-05-8 isofucoxanthinol 
• 143932-72-3 fucoxanthinol hemiketal 
• 7218-76-0 isofucoxanthin 
• 110241-03-7 fucoxanthin hemiketal 

Relevant articles and documents

Application of diphenyl diselenide as a new catalyst for photochemical stereoisomerization of carotenoids

In a comparative study, diphenyl diselenide was shown to be an alternative to iodine as a catalyst for photochemical E/Z isomerization of carotenoids. Suitable conditions for the stereomutation of zeaxanthin, violaxanthin, canlhaxanthin and fucoxanthin are reported. Photochemical allenic isomerization with increased R to S conversion was achieved by employing diphenyl diselenide rather than iodine as the catalyst. Reproducible and expedient artificial light conditions, avoiding insolation (sunlight), are reported. Diphenyl diselenide tolerated the presence of Huenig's base upon stereoisomerization of acid-sensitive carotenoids. Diphenyl ditelluride effected E/Z stereomutation, but no allenic R/S isomerization of fucoxanthin. The presence of base decreased the isomerization rate in the absence of catalyst and may serve to decrease undesirable E/Z stereoisomerization of base-stable carotenoids. Acta Chemica Scandinavica 1998.

Carotenoids and related polyenes. Part 3. First total synthesis of fucoxanthin and halocynthiaxanthin using oxo-metallic catalyst

The first total synthesis of optically active fucoxanthin 1 and halocynthiaxanthin 2 had been accomplished via the 8-oxo compound 5, efficiently prepared by rearrangement of the α-acetylenic alcohol 10 using oxo-metallic catalyst and subsequent iodine-catalysed double-bond shift.

Total synthesis of photosynthetic pigment fucoxanthin by use of oxo- metallic catalyst

The first total synthesis of optically active fucoxanthin 1 has been accomplished via the 8-oxo-compound 7, efficiently prepared by rearrangement of the α-acetylenic alcohol 2 using oxo-metallic catalyst and subsequent iodine catalyzed double bond-shift.