Fucoxanthin | CAS#3351-86-8

MedKoo Cat#: 329994 | Name: Fucoxanthin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fucoxanthin, also known as α-Carotene, is a carotenoid that occurs naturally in certain algae. 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.

Chemical Structure

Fucoxanthin

CAS#3351-86-8

Theoretical Analysis

MedKoo Cat#: 329994

Name: Fucoxanthin

CAS#: 3351-86-8

Chemical Formula: C42H58O6

Exact Mass: 658.4233

Molecular Weight: 658.92

Elemental Analysis: C, 76.56; H, 8.87; O, 14.57

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks

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Related CAS #

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Synonym

Fucoxanthin; Fucoxanthine; α-Carotene; Sebatrol;

IUPAC/Chemical Name

(1S,3R)-3-hydroxy-4-((R,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-octaen-1-ylidene)-3,5,5-trimethylcyclohexyl acetate

InChi Key

SJWWTRQNNRNTPU-XJUZQKKNSA-N

InChi Code

InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,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

SMILES Code

O=C(/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C([H])=[C@@]=C([C@@]1(O)C)C(C)(C[C@H](OC(C)=O)C1)C)C[C@]2(C3(C)C)[C@@](C)(C[C@@H](O)C3)O2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Research on how fucoxanthin may have preventive effects on cancer is also being done. Many studies show that it aids in anti-proliferation, cell cycle arrest, apoptosis induction, suppression of angiogenesis, and anti-drug potential. Without reducing its therapeutic efficacy, fucoxanthin could also reduce the toxicity that comes with the use of conventional medicine. More research in animal models of disease is needed to be done to obtain more conclusive evidence on the molecular basis of fucoxanthin action.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Fucoxanthin is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities.

In vitro activity:

Fucoxanthin significantly inhibited the viability of PC-3 cells in a time- and dose-dependent manner, and dose-dependently induced apoptosis of the cells (P < 0.05). Fucoxanthin-treated PC-3 cells showed significantly decreased mitochondrial membrane potential, mitochondrial fragmentation and increased superoxide level in the mitochondria (P < 0.05), and these effects of fucoxanthin were dose- dependent. Reference: Nan Fang Yi Ke Da Xue Xue Bao. 2021 Jun 20;41(6):953-959. https://pubmed.ncbi.nlm.nih.gov/34238751/

In vivo activity:

The mean IOP values of the rats in the blank control group were within the normal range (14.6 ± 1.2 mmHg), but these values were significantly higher among the rats in the PAMP LPS-induced uveitis group (23.2 ± 1.3 mmHg). Although LPS injection caused a significant increase in IOP, the effects of LPS were ameliorated by fucoxanthin. The IOP remained elevated in the groups treated with 0.1 and 1 mg/kg BW of fucoxanthin (21.3 ± 1.5 and 20.2 ± 1.1 mmHg, respectively) after LPS treatment, but the IOP was significantly reduced in the groups treated with 10 mg/kg BW of fucoxanthin (15.5 ± 0.8 mmHg) (Figure 2). Reference: Antioxidants (Basel). 2021 Jul; 10(7): 1092. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8301160/

	Solvent	mg/mL	mM
Solubility
	DMSO	16.3	24.66

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 658.92 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Li G, Chang X, Luo X, Zhao Y, Wang W, Kang X. [Fucoxanthin induces prostate cancer PC-3 cell apoptosis by causing mitochondria dysfunction and oxidative stress]. Nan Fang Yi Ke Da Xue Xue Bao. 2021 Jun 20;41(6):953-959. Chinese. doi: 10.12122/j.issn.1673-4254.2021.06.21. PMID: 34238751; PMCID: PMC8267986. 2. Chiang YF, Tsai CH, Chen HY, Wang KL, Chang HY, Huang YJ, Hong YH, Ali M, Shieh TM, Huang TC, Lin CI, Hsia SM. Protective Effects of Fucoxanthin on Hydrogen Peroxide-Induced Calcification of Heart Valve Interstitial Cells. Mar Drugs. 2021 May 26;19(6):307. doi: 10.3390/md19060307. PMID: 34073219; PMCID: PMC8227531. 3. Chen SJ, Lin TB, Peng HY, Lin CH, Lee AS, Liu HJ, Li CC, Tseng KW. Protective Effects of Fucoxanthin Dampen Pathogen-Associated Molecular Pattern (PAMP) Lipopolysaccharide-Induced Inflammatory Action and Elevated Intraocular Pressure by Activating Nrf2 Signaling and Generating Reactive Oxygen Species. Antioxidants (Basel). 2021 Jul 7;10(7):1092. doi: 10.3390/antiox10071092. PMID: 34356327; PMCID: PMC8301160. 4. Oliyaei N, Moosavi-Nasab M, Tamaddon AM, Tanideh N. Antidiabetic effect of fucoxanthin extracted from Sargassumangustifolium on streptozotocin-nicotinamide-induced type 2 diabetic mice. Food Sci Nutr. 2021 May 6;9(7):3521-3529. doi: 10.1002/fsn3.2301. PMID: 34262712; PMCID: PMC8269564.

In vitro protocol:

In vivo protocol:

1. Chen SJ, Lin TB, Peng HY, Lin CH, Lee AS, Liu HJ, Li CC, Tseng KW. Protective Effects of Fucoxanthin Dampen Pathogen-Associated Molecular Pattern (PAMP) Lipopolysaccharide-Induced Inflammatory Action and Elevated Intraocular Pressure by Activating Nrf2 Signaling and Generating Reactive Oxygen Species. Antioxidants (Basel). 2021 Jul 7;10(7):1092. doi: 10.3390/antiox10071092. PMID: 34356327; PMCID: PMC8301160. 2. Oliyaei N, Moosavi-Nasab M, Tamaddon AM, Tanideh N. Antidiabetic effect of fucoxanthin extracted from Sargassumangustifolium on streptozotocin-nicotinamide-induced type 2 diabetic mice. Food Sci Nutr. 2021 May 6;9(7):3521-3529. doi: 10.1002/fsn3.2301. PMID: 34262712; PMCID: PMC8269564.

1: Jin Y, Qiu S, Shao N, Zheng J. Fucoxanthin and Tumor Necrosis Factor-Related Apoptosis-Inducing Ligand (TRAIL) Synergistically Promotes Apoptosis of Human Cervical Cancer Cells by Targeting PI3K/Akt/NF-κB Signaling Pathway. Med Sci Monit. 2018 Jan 1;24:11-18. PubMed PMID: 29291370; PubMed Central PMCID: PMC5759513. 2: Ye GL, Du DL, Jin LJ, Wang LL. Sensitization of TRAIL-resistant cervical cancer cells through combination of TRAIL and fucoxanthin treatments. Eur Rev Med Pharmacol Sci. 2017 Dec;21(24):5594-5601. doi: 10.26355/eurrev_201712_14000. PubMed PMID: 29271991. 3: Zeng J, Zhang Y, Ruan J, Yang Z, Wang C, Hong Z, Zuo Z. Protective effects of fucoxanthin and fucoxanthinol against tributyltin-induced oxidative stress in HepG2 cells. Environ Sci Pollut Res Int. 2017 Dec 8. doi: 10.1007/s11356-017-0661-3. [Epub ahead of print] PubMed PMID: 29222657. 4: Rebello CJ, Greenway FL, Johnson WD, Ribnicky D, Poulev A, Stadler K, Coulter AA. Fucoxanthin and Its Metabolite Fucoxanthinol Do Not Induce Browning in Human Adipocytes. J Agric Food Chem. 2017 Dec 20;65(50):10915-10924. doi: 10.1021/acs.jafc.7b03931. Epub 2017 Dec 8. PubMed PMID: 29172481; PubMed Central PMCID: PMC5751931. 5: Chang YH, Chen YL, Huang WC, Liou CJ. Fucoxanthin attenuates fatty acid-induced lipid accumulation in FL83B hepatocytes through regulated Sirt1/AMPK signaling pathway. Biochem Biophys Res Commun. 2018 Jan 1;495(1):197-203. doi: 10.1016/j.bbrc.2017.11.022. Epub 2017 Nov 4. PubMed PMID: 29113798. 6: Yu RX, Yu RT, Liu Z. Inhibition of two gastric cancer cell lines induced by fucoxanthin involves downregulation of Mcl-1 and STAT3. Hum Cell. 2018 Jan;31(1):50-63. doi: 10.1007/s13577-017-0188-4. Epub 2017 Nov 6. PubMed PMID: 29110251. 7: Zhang T, Liu C, Dong W, Wang W, Sun Y, Chen X, Yang C, Dai N. Photoelectrochemical Complexes of Fucoxanthin-Chlorophyll Protein for Bio-Photovoltaic Conversion with a High Open-Circuit Photovoltage. Chem Asian J. 2017 Dec 5;12(23):2996-2999. doi: 10.1002/asia.201701296. Epub 2017 Nov 2. PubMed PMID: 29024505. 8: Lin J, Yu J, Zhao J, Zhang K, Zheng J, Wang J, Huang C, Zhang J, Yan X, Gerwick WH, Wang Q, Cui W, He S. Fucoxanthin, a Marine Carotenoid, Attenuates β-Amyloid Oligomer-Induced Neurotoxicity Possibly via Regulating the PI3K/Akt and the ERK Pathways in SH-SY5Y Cells. Oxid Med Cell Longev. 2017;2017:6792543. doi: 10.1155/2017/6792543. Epub 2017 Aug 8. PubMed PMID: 28928905; PubMed Central PMCID: PMC5591933. 9: Rajauria G, Foley B, Abu-Ghannam N. Characterization of dietary fucoxanthin from Himanthalia elongata brown seaweed. Food Res Int. 2017 Sep;99(Pt 3):995-1001. doi: 10.1016/j.foodres.2016.09.023. Epub 2016 Sep 22. PubMed PMID: 28865626. 10: Lopes-Costa E, Abreu M, Gargiulo D, Rocha E, Ramos AA. Anticancer effects of seaweed compounds fucoxanthin and phloroglucinol, alone and in combination with 5-fluorouracil in colon cells. J Toxicol Environ Health A. 2017;80(13-15):776-787. doi: 10.1080/15287394.2017.1357297. Epub 2017 Aug 29. PubMed PMID: 28850007. 11: Khoroshyy P, Bína D, Gardian Z, Litvín R, Alster J, Pšenčík J. Quenching of chlorophyll triplet states by carotenoids in algal light-harvesting complexes related to fucoxanthin-chlorophyll protein. Photosynth Res. 2017 Jul 1. doi: 10.1007/s11120-017-0416-5. [Epub ahead of print] PubMed PMID: 28669083. 12: Ma SY, Park WS, Lee DS, Choi G, Yim MJ, Lee JM, Jung WK, Park SG, Seo SK, Park SJ, Han IY, Choi YH, Choi IW. Fucoxanthin inhibits profibrotic protein expression in vitro and attenuates bleomycin-induced lung fibrosis in vivo. Eur J Pharmacol. 2017 Sep 15;811:199-207. doi: 10.1016/j.ejphar.2017.06.022. Epub 2017 Jun 19. PubMed PMID: 28642129. 13: Mikami N, Hosokawa M, Miyashita K, Sohma H, Ito YM, Kokai Y. Reduction of HbA1c levels by fucoxanthin-enriched akamoku oil possibly involves the thrifty allele of uncoupling protein 1 (UCP1): a randomised controlled trial in normal-weight and obese Japanese adults. J Nutr Sci. 2017 Feb 14;6:e5. doi: 10.1017/jns.2017.1. eCollection 2017. PubMed PMID: 28620480; PubMed Central PMCID: PMC5465861. 14: Xiang S, Liu F, Lin J, Chen H, Huang C, Chen L, Zhou Y, Ye L, Zhang K, Jin J, Zhen J, Wang C, He S, Wang Q, Cui W, Zhang J. Fucoxanthin Inhibits β-Amyloid Assembly and Attenuates β-Amyloid Oligomer-Induced Cognitive Impairments. J Agric Food Chem. 2017 May 24;65(20):4092-4102. doi: 10.1021/acs.jafc.7b00805. Epub 2017 May 11. PubMed PMID: 28478680. 15: Yu J, Lin JJ, Yu R, He S, Wang QW, Cui W, Zhang JR. Fucoxanthin prevents H(2)O(2)-induced neuronal apoptosis via concurrently activating the PI3-K/Akt cascade and inhibiting the ERK pathway. Food Nutr Res. 2017 Mar 28;61(1):1304678. doi: 10.1080/16546628.2017.1304678. eCollection 2017. PubMed PMID: 28469544; PubMed Central PMCID: PMC5404425. 16: Zhang L, Wang H, Fan Y, Gao Y, Li X, Hu Z, Ding K, Wang Y, Wang X. Fucoxanthin provides neuroprotection in models of traumatic brain injury via the Nrf2-ARE and Nrf2-autophagy pathways. Sci Rep. 2017 Apr 21;7:46763. doi: 10.1038/srep46763. PubMed PMID: 28429775; PubMed Central PMCID: PMC5399453. 17: Sellimi S, Ksouda G, Benslima A, Nasri R, Rinaudo M, Nasri M, Hajji M. Enhancing colour and oxidative stabilities of reduced-nitrite turkey meat sausages during refrigerated storage using fucoxanthin purified from the Tunisian seaweed Cystoseira barbata. Food Chem Toxicol. 2017 Sep;107(Pt B):620-629. doi: 10.1016/j.fct.2017.04.001. Epub 2017 Apr 4. PubMed PMID: 28389351. 18: Lin HV, Tsou YC, Chen YT, Lu WJ, Hwang PA. Effects of Low-Molecular-Weight Fucoidan and High Stability Fucoxanthin on Glucose Homeostasis, Lipid Metabolism, and Liver Function in a Mouse Model of Type II Diabetes. Mar Drugs. 2017 Apr 7;15(4). pii: E113. doi: 10.3390/md15040113. PubMed PMID: 28387741; PubMed Central PMCID: PMC5408259. 19: Kuznetsova V, Chábera P, Litvín R, Polívka T, Fuciman M. Effect of Isomerization on Excited-State Dynamics of Carotenoid Fucoxanthin. J Phys Chem B. 2017 May 4;121(17):4438-4447. doi: 10.1021/acs.jpcb.7b02526. Epub 2017 Apr 25. PubMed PMID: 28382818. 20: Satomi Y. Antitumor and Cancer-preventative Function of Fucoxanthin: A Marine Carotenoid. Anticancer Res. 2017 Apr;37(4):1557-1562. Review. PubMed PMID: 28373414.