all-trans-Fucoxanthin

Base Information

• Chemical Name: all-trans-Fucoxanthin
• CAS No.: 3351-86-8
• Molecular Formula: C₄₂H₅₈O₆
• Molecular Weight: 658.919
• Hs Code.: 29153900
• Mol file: 3351-86-8.mol

Synonyms:all-trans-Fucoxanthin;Fucoxanthin, all-trans-;SCHEMBL2950208;SJWWTRQNNRNTPU-BWRPRJLXSA-N;.beta.,.beta.-Carotene, 3'-(acetyloxy)-6',7'-didehydro-5,6-epoxy-5,5',6,6',7,8-hexahydro-3,5'-dihydroxy-8-oxo-, (3S,3'S,5R,5'R,6S,6'R)-;AKOS040759184;A858021;[(1S,3R)-3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaenylidene]-3,5,5-trimethylcyclohexyl] acetate;3'-acetate-(7CI)-6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-a-carotene;3'-acetate-(7CI)-6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-alpha-carotene;3-Hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-(4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3,7,12,16-tetramethyl-17-oxo-1,3,5,7,9,11,13,15-octadecaoctaenylidene]-3,5,5-trimethylcyclohexyl acet #

Chemical Property of all-trans-Fucoxanthin

Chemical Property:

• Appearance/Colour: Crystalline solid
• Melting Point: 166-168 °C
• Refractive Index: 1.563
• Boiling Point: 764.1 °C at 760 mmHg
• PKA: 14.47±0.60(Predicted)
• Flash Point: 223 °C
• PSA: 96.36000
• Density: 1.09 g/cm³
• LogP: 8.69220
• Storage Temp.: ?20°C
• Solubility.: Ethanol,
• XLogP3: 8.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 658.42333957
• Heavy Atom Count: 48
• Complexity: 1530

Purity/Quality:

98% ^*data from raw suppliers

Fucoxanthin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16-24/25

MSDS Files:

SDS file from LookChem

Useful:

• 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
• Isomeric SMILES: C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C(=O)CC12C(CC(CC1(O2)C)O)(C)C)/C=C/C=C(\C)/C=C=C3C(CC(CC3(C)O)OC(=O)C)(C)C
• Description: Fucoxanthin is another important xanthophyll. It is widely found in heterokontophyta, such as brown algae and oceanic microalgae,and is believed be the second-most abundant carotenoid on Earth after β-carotene. Recently, studies on the functionality of fucoxanthin have been increasingly conducted,and fucoxanthin has been shown to possess various beneficial physiological activities.It has various pharmaceutical effects such as anti-tumor, anti-inflammatory, anti-oxidant, anti-obesity effects, protecting nerve cell, increasing the content of ARA(arachidonic acid) and DHA (docosahexaenoic acid) in mice; It is widely used as medicine, skin care and beauty industry, and in the Food supplements market.
• 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. 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. 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.

Technology Process of all-trans-Fucoxanthin

There total 2 articles about all-trans-Fucoxanthin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 28.0%

Acetic acid (1S,3R)-3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7,12,16-tetramethyl-17-oxo-octadeca-1,3,5,7,9,11,13,15-octaenylidene]-3,5,5-trimethyl-cyclohexyl ester → fucoxanthin (3351-86-8,17257-05-5,55659-36-4,55659-37-5,55659-38-6,92761-37-0,124378-42-3,138126-73-5,141270-13-5,141270-14-6,141270-15-7,141270-16-8) + Acetic acid (1S,3R)-3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-((1R,4S,6S)-4-hydroxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-3,7,12,16-tetramethyl-17-oxo-octadeca-1,3,5,7,9,11,13,15-octaenylidene]-3,5,5-trimethyl-cyclohexyl ester

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid;

DOI:10.1248/cpb.42.410

Reference yield:

→ fucoxanthin (3351-86-8,17257-05-5,55659-36-4,55659-37-5,55659-38-6,92761-37-0,124378-42-3,138126-73-5,141270-13-5,141270-14-6,141270-15-7,141270-16-8)

Guidance literature:

With iodine; for 8h; Irradiation; sunlight;

DOI:10.3891/acta.chem.scand.52-1263

Reference yield: 90.0%

acetic anhydride (108-24-7) + fucoxanthin (3351-86-8,17257-05-5,55659-36-4,55659-37-5,55659-38-6,92761-37-0,124378-42-3,138126-73-5,141270-13-5,141270-14-6,141270-15-7,141270-16-8) → fucoxanthin monoacetate (3351-87-9)

Guidance literature:

In pyridine;

Downstream raw materials:

2,2-dimethylsuccinic acid

3'R,4'-<(2R,4S)-2-hydroxy-4-acetoxy-2,6,6-trimethylcyclohexylidene>but-3'-en-2'-one

fucoxanthin monoacetate

fucoxanthinol

Refernces

• 1、 Yamano, Yumiko,Tode, Chisato,Ito, Masayoshi. "Carotenoids and related polyenes. Part 3. First total synthesis of fucoxanthin and halocynthiaxanthin using oxo-metallic catalyst". . p. 1895 - 1904. Retrieved 2007/10/02.