U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C40H52O4
Molecular Weight 596.8385
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 9
Charge 0

SHOW SMILES / InChI
Structure of ASTAXANTHIN, MESO-

SMILES

CC(\C=C\C=C(C)\C=C\C1=C(C)C(=O)[C@@H](O)CC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)[C@H](O)CC2(C)C

InChI

InChIKey=MQZIGYBFDRPAKN-GNBIBNSWSA-N
InChI=1S/C40H52O4/c1-27(17-13-19-29(3)21-23-33-31(5)37(43)35(41)25-39(33,7)8)15-11-12-16-28(2)18-14-20-30(4)22-24-34-32(6)38(44)36(42)26-40(34,9)10/h11-24,35-36,41-42H,25-26H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,27-15+,28-16+,29-19+,30-20+/t35-,36+

HIDE SMILES / InChI

Molecular Formula C40H52O4
Molecular Weight 596.8385
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 9
Optical Activity UNSPECIFIED

Meso-astaxanthin is one of three naturally occurring optical isomers of astaxanthin. Astaxanthins are a group of compounds providing red pigmentation in trout, salmon, lobster, shrimp and other sea creatures. Synthetic astraxanthins and biomass containing astraxanthins are used as feed additives in commercial fishing operations to ensure redness of the flesh. Astaxanthins as a group also exhibit antioxidant properties and are marketed in a number of nutriceutical products for human consumption. Isomers astaxanthin including meso-astaxanthin has demonstrated the ability to slow the growth of colon cancer cells in vitro.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.51 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Plasma appearance of unesterified astaxanthin geometrical E/Z and optical R/S isomers in men given single doses of a mixture of optical 3 and 3'R/S isomers of astaxanthin fatty acyl diesters.
2004 Oct
Bioavailability of astaxanthin stereoisomers from wild (Oncorhynchus spp.) and aquacultured (Salmo salar) salmon in healthy men: a randomised, double-blind study.
2008 May
Patents

Sample Use Guides

Three male volunteers consumed a meal containing a 10-mg dose of astaxanthin from astaxanthin diesters, followed by a meal with a dose of 100 mg astaxanthin four weeks later. HPLC analysis of the astaxanthins showed 95.2% all-E-, 1.2% 9Z- and 3.6% 13Z-astaxanthin, of (3R,3'R)-, (3R,3'S; meso)- and (3S,3'S)-astaxanthin in a 31:49:20 ratio. Plasma astaxanthin time curves were measured over 76 hours post meal. The (3R,3'R)-astaxanthin optical isomer accumulated selectively in plasma compared to the (3R,3'S)- and (3S,3'S)-isomers, and comprised 54% of total astaxanthin in the blood and only 31% of total astaxanthin in the administered dose.
Route of Administration: Oral
Human colon cancer cells HCT116 and H29 were cultured with RPMI1640 media supplemented with 5% heat-inactivated fetal bovine serum, 100 U/mL of penicillin, and 0.1 mg/mL of streptomycin at 37 deg-C in a 5% CO2 atmosphere. Cells were seeded in 96-well plates. After 24 hours, media was exchanged with 200 micro-L of complete media by the presence of serial concentrations meso-astaxanthin (4, 6, 8, 10, 12, 14 and 16 micro-M) for 24, 48, and 72 hours. After the specified time the culture media was hanged with MTT-containing medium and assayed for cell viability. Meso-astaxanthin inhibited HCT116 and HT29 colon cancer cell growth in a dose-dependent and time-dependent manner. The inhibitory rate was dramatically enhanced by increases in concentration and extension of treatment time. The IC50 of Meso-astaxanthin after 72 hours was 7.51 micro-M.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:42:39 GMT 2023
Edited
by admin
on Sat Dec 16 09:42:39 GMT 2023
Record UNII
8678E0R020
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASTAXANTHIN, MESO-
Common Name English
(3R,3'S)-ALL-TRANS-ASTAXANTHIN
Common Name English
(3S,3'R)-4-KETOZEAXANTHIN
Common Name English
MESO-ASTAXANTHIN
Common Name English
.BETA.,.BETA.-CAROTENE-4,4'-DIONE, 3,3'-DIHYDROXY-, (3R,3'S)-
Systematic Name English
(3R,3'S)-ASTAXANTHIN
Common Name English
Code System Code Type Description
FDA UNII
8678E0R020
Created by admin on Sat Dec 16 09:42:39 GMT 2023 , Edited by admin on Sat Dec 16 09:42:39 GMT 2023
PRIMARY
PUBCHEM
12358422
Created by admin on Sat Dec 16 09:42:39 GMT 2023 , Edited by admin on Sat Dec 16 09:42:39 GMT 2023
PRIMARY
CAS
71772-51-5
Created by admin on Sat Dec 16 09:42:39 GMT 2023 , Edited by admin on Sat Dec 16 09:42:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID501316653
Created by admin on Sat Dec 16 09:42:39 GMT 2023 , Edited by admin on Sat Dec 16 09:42:39 GMT 2023
PRIMARY
CHEBI
80217
Created by admin on Sat Dec 16 09:42:39 GMT 2023 , Edited by admin on Sat Dec 16 09:42:39 GMT 2023
PRIMARY