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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H58O6
Molecular Weight 658.9063
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 9
Charge 0

SHOW SMILES / InChI
Structure of FUCOXANTHIN

SMILES

CC(=O)O[C@H]1CC(C)(C)C(=C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C(=O)C[C@@]23O[C@]2(C)C[C@@H](O)CC3(C)C)[C@](C)(O)C1

InChI

InChIKey=SJWWTRQNNRNTPU-XJUZQKKNSA-N
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

HIDE SMILES / InChI

Molecular Formula C42H58O6
Molecular Weight 658.9063
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 9
Optical Activity UNSPECIFIED

Fucoxanthin isis a marine carotenoid mainly found in brown algae, giving them a brown or olive-green color. Fucoxanthin is investigated for its anti-inflammatory, antinociceptive and anti-cancer effects. In vivo studies have demonstrated that oral administration of fucoxanthin inhibited carcinogenesis in an animal model of duodenal, skin, colon and liver cancer. Fucoxanthin causes antitumor and anticarcinogenic effects by inducing G1 cell-cycle arrest and apoptosis by modulating expression of various cellular molecules and cellular signal transduction pathways, but the exact mechanism of anti-cancer action of fucoxanthin is not fully elucidated. Fucoxanthin regulates lipids metabolism, the effect most likely mediated by AMK-activated protein kinase. A clinical trial of fucoxanthin against non-alcoholic fatty liver disease is ongoing.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Fucoxanthin induces apoptosis in human leukemia HL-60 cells through a ROS-mediated Bcl-xL pathway.
2010 Sep
Anti-inflammatory effect of fucoxanthin derivatives isolated from Sargassum siliquastrum in lipopolysaccharide-stimulated RAW 264.7 macrophage.
2012 Sep
The anti-apoptotic effect of fucoxanthin on carbon tetrachloride-induced hepatotoxicity.
2013 Feb
Patents

Sample Use Guides

In a clinical trial against non-alcoholic fatty liver disease fucoxanthin is administered orally as a component of FucoHiQ capsules. Each serving contains 275 mg of fucoxanthin, 6 capsules per day are administered.
Route of Administration: Oral
Human non-small cell lung cancer cells were treated with 12.5-100 uM of fucoxanthin for 24-72 hours. Cytotoxic activity was evaluated by the Cell counting kit-8 and the absorbance was measured at 450 nm.
Substance Class Chemical
Created
by admin
on Sat Dec 16 03:05:43 UTC 2023
Edited
by admin
on Sat Dec 16 03:05:43 UTC 2023
Record UNII
06O0TC0VSM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FUCOXANTHIN
INCI   MI   WHO-DD  
INCI  
Official Name English
FUCOXANTHIN [MI]
Common Name English
Fucoxanthin [WHO-DD]
Common Name English
.ALPHA.-CAROTENE, 6',7'-DIDEHYDRO-5,6-EPOXY-4',5,5',6,7,8-HEXAHYDRO-3,3',5'-TRIHYDROXY-8-OXO-, 3'-ACETATE
Common Name English
CHEBI:5186
Code English
ALL-TRANS-FUCOXANTHIN
Common Name English
ALL-E-(3S,5R,6S,3'S,5'R,6'R)-FUCOXANTHIN
Common Name English
FUCOXANTHIN [INCI]
Common Name English
.ALPHA.-CAROTENE, 6',7'-DIDEHYDRO-5,6-EPOXY-4',5,5',6,7,8-HEXAHYDRO-3,3',5'-TRIHYDROXY-8-OXO-, 3'-ACETATE, ALL-TRANS-
Common Name English
6',7'-DIDEHYDRO-5,6-EPOXY-4',5,5',6,7,8-HEXAHYDRO-3,3',5'-TRIHYDROXY-8-OXO-.ALPHA.-CAROTENE 3'-ACETATE
Common Name English
.BETA.,.BETA.-CAROTEN-8(5H)-ONE, 6',7'-DIDEHYDRO-5,6-EPOXY-4',5',6,7-TETRAHYDRO-3,3',5'-TRIHYDROXY-, (3S,3'S,5R,5'R,6S,6'R)-
Common Name English
FUCOXANTHIN, ALL-TRANS-
Common Name English
(3S,3'S,5R,5'R,6S,6'R)-6',7'-DIDEHYDRO-5,6-EPOXY-4',5',6,7-TETRAHYDRO-3,3',5'-TRIHYDROXY-.BETA.,.BETA.-CAROTEN-8(5H)-ONE
Common Name English
SEBATROL
Common Name English
Classification Tree Code System Code
DSLD 664 (Number of products:35)
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
Code System Code Type Description
WIKIPEDIA
FUCOXANTHIN
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY
EVMPD
SUB60248
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY
CHEBI
5186
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY
MESH
C025164
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY
SMS_ID
100000134210
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY
DRUG BANK
DB15462
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY
FDA UNII
06O0TC0VSM
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY
MERCK INDEX
m5580
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID901031617
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY
CAS
3351-86-8
Created by admin on Sat Dec 16 03:05:43 UTC 2023 , Edited by admin on Sat Dec 16 03:05:43 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
Unit; ng/g; The content of carotenoids from selected commercially available health supplements (Spirulina)
ASSAY (HPLC)
Batch Data