Astaxanthin CAS#: 472-61-7; ChemWhat Code: 52082
Identification
| Product Name | Astaxanthin |
| IUPAC Name | (6S)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethylcyclohex-2-en-1-one |
| Molecular Structure |  |
| CAS Registry Number | 472-61-7 |
| EINECS Number | 207-451-4 |
| Synonyms | Astaxanthin 472-61-7 Ovoester all-trans-Astaxanthin AstaREAL 3,3′-Dihydroxy-beta,beta-carotene-4,4′-dione Astaxanthine BioAstin (3S,3’S)-Astaxanthin trans-Astaxanthin Astaxanthin, (3S,3’S)- (3S,3’S)-all-trans-Astaxanthin 8XPW32PR7I 3,3′-Dihydroxy-beta-carotene-4,4′-dione (3S,3’S)-3,3′-Dihydroxy-beta,beta-carotene-4,4′-dione CHEBI:40968 NSC-635689 (6S,6’S)-3,3′-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)bis(6-hydroxy-2,4,4-trimethylcyclohex-2-enone) .beta.,.beta.-Carotene-4,4′-dione, 3,3′-dihydroxy-, (3S,3’S)- Algae Haematococcus pluvialis (6S)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethylcyclohex-2-en-1-one Natupink AstaXin Carophyll Pink Lucantin Pink BioAstin oleoresin (6S)-6-Hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexenyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethyl-1-cyclohex-2-enone Astaxanthin (6CI) Astaxanthin, all-trans- UNII-8XPW32PR7I astaxantin CCRIS 7118 HSDB 7468 EINECS 207-451-4 NSC 635689 3S,3’S-Astaxanthin Astaxanthin, all-trans-, (3S,3’S)- Astaxanthin, 5% active ASTAXANTHIN [MI] b-Carotene-4,4′-dione ASTAXANTHIN [HSDB] ASTAXANTHIN [INCI] ASTAXANTHIN [VANDF] beta-Carotene-4,4′-dione ASTAXANTHIN [MART.] SCHEMBL20047 ASTAXANTHIN [USP-RS] ASTAXANTHIN [WHO-DD] E161j CHEMBL1255871 Astaxanthin, >=98% (HPLC) E 161j DTXSID00893777 all-trans-(3S,3’S)-astaxanthin 3,3′-Dihydroxy-beta,beta-carotene-4,4′-dione, (3S,3’S)- HMS3885C08 BCP05821 HY-B2163 LMPR01070263 MFCD00672621 s3834 AKOS015841055 AKOS015895756 AC-8760 BCP9000329 CCG-270185 DB06543 all-trans-Astaxanthin, analytical standard AS-14095 CS-0020413 NS00018032 C08580 M01303 3,3′-dihydroxy-4,4′-diketo-beta,beta-carotene A827177 Q413740 Q-200655 3,3′-DIHYDROXY-4,4′-DIKETO-.BETA.-CAROTENE all-trans-3,3′-dihydroxy-b-Carotene-4,4′-dione (8CI) .beta.-Carotene-4,4′-dione, 3,3′-dihydroxy-, all-trans- 3-(4,6-Dimethyl-2-oxo-2H-pyrimidin-1-yl)-propionicacid all-trans-3,3′-dihydroxy-beta-Carotene-4,4′-dione (8CI) 3,3′-Dihydroxy-.beta.,.beta.-carotene-4,4′-dione, (3S,3’S)- (3S,3’S)-3,3′-DIHYDROXY-.BETA.,.BETA.-CAROTENE-4,4′-DIONE 3,3′-Dihydroxy-beta,beta-carotene-4,4′-dione;(S)-6-hydroxy-3-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-((S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-enyl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl)-2,4,4-trimethylcyclohex-2-enone; |
| Molecular Formula | C40H52O4 |
| Molecular Weight | 596.8 |
| InChI | 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-/m0/s1 |
| InChI Key | MQZIGYBFDRPAKN-UWFIBFSHSA-N |
| Isomeric SMILES | CC1=C(C(C[C@@H](C1=O)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C(=O)[C@H](CC2(C)C)O)C)\C)\C)/C)/C |
Physical Data
| Appearance | red or dark red powder |
| Loss on Drying | ≤5% |
| Melting Point, °C | Solvent (Melting Point) |
| 224 | |
| 213.2 – 217.4 | |
| 216 | petroleum ether |
| 214 | methanol |
| 223 – 225 | |
| 216 – 219 |
| Description (Association (MCS)) | Solvent (Association (MCS)) | Partner (Association (MCS)) |
| Association with compound | ligand-binding domain of carotenoid-binding protein from Bombyx mori supplemented by His-tag | |
| Association with compound | ethanol, water | glycyrrhizin |
| Association with compound | H2O | C78H54O24S6(6-)*6Na(1+) |
| Association with compound | H2O | C65H45O20S5(5-)*5Na(1+) |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | ||
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 600 | |
| Chemical shifts, Spectrum | 13C | dimethylsulfoxide-d6 | 150.9 | |
| Chemical shifts | 1H | chloroform-d1 | 300 | |
| Spectrum | 1H | [(2)H6]acetone | 26.84 | 600 |
| HSQC (Heteronuclear Single Quantum Coherence) | 1H, 13C | [(2)H6]acetone | 26.84 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) |
| Bands, Spectrum | |
| Spectrum | potassium bromide |
| Bands | potassium bromide |
| Intensity of IR bands, Bands, Spectrum | potassium bromide |
| Bands | Br |
| Intensity of IR bands |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) |
| Spectrum | dimethyl sulfoxide |
| Spectrum | |
| Spectrum | methanol |
| Spectrum | |
| Spectrum | thanol, water |
Route of Synthesis (ROS)
| Conditions | Yield |
| With pyridine In dichloromethane at 20℃; Concentration; Reagent/catalyst; Temperature; Solvent; Experimental Procedure 8 EXAMPLE 8: SYNTHESIS OF ASTAXANTHIN DIHEXADECANOATE 10120] 7.6 g (12.7 mmol) of astaxanthin and 2.98 g (37.7 mmol) of pyridine are charged in 75.9 g of dichloromethane and 9.42 g (34.3 mmol) of hexadecanoyl chloride are added dropwise at 20° C. over 5 minutes. The reaction mixture is allowed to react overnight, the mixture diluted with 75.9 g of dichloromethane, 0.37 g of methanol and, 30 mm later, 11.4 g of water are added and the phases separated. The lower phase is washed with 11.4 g of 10% hydrochloric acid and then twice with 11.4 g of water. The organic phase is rotary evaporated at 50° C., the residue is taken up in ca. 217 ml of t-butyl methyl ether and again thlly concentrated. The residue is virtually dissolved in 217 ml of ethyl acetate at 50° C. and 108 ml of ethanol is added dropwise. The mixture is initially cooled to 45° C. and then to 0° C. over 17 h. The precipitated crystalline solid is filtered off under suction, washed twice with 72 ml of ethanol each time and dried at 40° C. in a vacuum drying cabinet. 10 g (73% yield) of astaxanthin dihexadecanoate (m.p. 79.7° C.) are obtained. | 73% |
Safety and Hazards
No data available
Other Data
No data available
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 596.85 |
| logP | 9.696 |
| HBA | 4 |
| HBD | 2 |
| Matching Lipinski Rules | 2 |
| Veber rules component | |
| Polar Surface Area (PSA) | 74.6 |
| Rotatable Bond (RotB) | 10 |
| Matching Veber Rules | 2 |
| Use Pattern |
| Astaxanthin CAS#: 472-61-7 possesses strong antioxidant properties, helping to neutralize free radicals and reduce oxidative stress on cells. This contributes to maintaining cell health and slowing the aging process. And Astaxanthin exhibits potent antioxidant effects, indirectly exerting anti-inflammatory actions by modulating the balance between free radicals and antioxidants in the body. Astaxanthin significantly reduces the levels of markers of DNA damage and lowers plasma C-reactive protein concentrations, confirming its anti-inflammatory effects on the human body. |
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