Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C40H52O4 |
Molecular Weight | 596.8385 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 9 |
Charge | 0 |
SHOW SMILES / InChI
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-OXBRSLPGSA-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-/m1/s1
(R, R)-astaxanthin is the naturally occurring enantiomer of astaxanthin and can be isolated from the yeast Phaffia rhodozyma and from Antarctic krill. Biomass of killed dead Phaffia rhodozyma is fed to salmon and trout to ensure red flesh pigmentation due to its high content of assorted astaxanthins. Astaxanthin and its stereoisomers have demonstrated the ability to inhibit the growth of colon cancer cells in-vitro.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0007050 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27726394 |
7.48 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseBiomass of killed dead Phaffia rhodozyma is fed to salmon and trout to ensure red flesh pigmentation due to its high content of assorted astaxanthins. |
PubMed
Title | Date | PubMed |
---|---|---|
Accumulation of astaxanthin all-E, 9Z and 13Z geometrical isomers and 3 and 3' RS optical isomers in rainbow trout (Oncorhynchus mykiss) is selective. | 1999 Feb |
|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15556071
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27726394
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 (R, R)-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. (R, R)-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 (R, R)-astaxanthin after 72 hours was 7.48 micro-M.
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60760-95-4
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12358421
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8L22ANN83S
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SUBSTANCE RECORD