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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
Structure of ASTAXANTHIN, (R,R)-

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

HIDE SMILES / InChI
(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

Targets

Primary TargetPharmacologyConditionPotency
7.48 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

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.
PubMed

PubMed

TitleDatePubMed
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

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 (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.
Name Type Language
ASTAXANTHIN, (R,R)-
Common Name English
(3R,3'R)-ALL-TRANS-ASTAXANTHIN
Common Name English
ASTAXANTHIN, (3R,3'R)-
Common Name English
.BETA.,.BETA.-CAROTENE-4,4'-DIONE, 3,3'-DIHYDROXY-, (3R,3'R)-
Systematic Name English
TRANS-(3R,3'R)-ASTAXANTHIN
Common Name English
(R,R)-ASTAXANTHIN
Common Name English
(3R,3'R)-ASTAXANTHIN
Common Name English
Code System Code Type Description
CAS
60760-95-4
Created by admin on Sat Dec 16 09:42:38 GMT 2023 , Edited by admin on Sat Dec 16 09:42:38 GMT 2023
PRIMARY
PUBCHEM
12358421
Created by admin on Sat Dec 16 09:42:38 GMT 2023 , Edited by admin on Sat Dec 16 09:42:38 GMT 2023
PRIMARY
FDA UNII
8L22ANN83S
Created by admin on Sat Dec 16 09:42:38 GMT 2023 , Edited by admin on Sat Dec 16 09:42:38 GMT 2023
PRIMARY