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CAS No. : | 472-61-7 | MDL No. : | MFCD00672621 |
Formula : | C40H52O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MQZIGYBFDRPAKN-UWFIBFSHSA-N |
M.W : | 596.84 | Pubchem ID : | 5281224 |
Synonyms : |
|
Num. heavy atoms : | 44 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 10 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 187.16 |
TPSA : | 74.6 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -2.65 cm/s |
Log Po/w (iLOGP) : | 6.59 |
Log Po/w (XLOGP3) : | 10.27 |
Log Po/w (WLOGP) : | 8.91 |
Log Po/w (MLOGP) : | 5.09 |
Log Po/w (SILICOS-IT) : | 10.33 |
Consensus Log Po/w : | 8.24 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -9.35 |
Solubility : | 0.000000266 mg/ml ; 0.0000000004 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -11.77 |
Solubility : | 0.000000001 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
Log S (SILICOS-IT) : | -5.68 |
Solubility : | 0.00124 mg/ml ; 0.00000208 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 6.53 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: With sodium methylate In methanol at 0℃; for 2 h; Stage #2: With acetic acid In methanol; water at 20 - 75℃; for 20 h; Heating / reflux |
71,9 g (0, 125 mol) ASTAXANTHIN-C15-PHOSPHONIUMSALZ P5 (X~ = BRO- mid) wurden in 150 ML Methanol vorgelegt. Bei 0C gab man 11,4 g GIO-DIAL Ia (95percent ig ; das entspricht 0,0475 mol) zu. Dann tropfte man innerhalb von 1H bei 0C 24,8 g einer 30percent igen Lsung von Natriummethylat in Methanol (= 0,137 mol NaOMe) zu, rhrte eine weitere Stunde bei 0C nach und lies dann auf Raumtemperatur kom- men. Man tropfte eine Lsung von 1,5 G (25 mmol) Essigsure in 115 ml Wasser zu, erhitzte auf Rckfluss (ca. 75C) und rhrte 20 h unter Rckfluss nach. Man lies auf Raumtemperatur kommen und filtrierte das Kristallisat ab. Der Filterkuchen wurde zweimal MIT JE 100 ML EINES 60 : 40 (V/V) -GEMISCHES AUS METHANOL/WASSER, einmal mit heiem Wasser (100 ml) und einmal mit Methanol (100 ml ; 25C) gewaschen und im Vakuumtrockenschrank bei +50C getrocknet. Auswaage : 23,5 g Astaxanthin = 83, 0percent Ausbeute (bezogen auf eingesetztes Ia) ; Reinheit nach HPLC : 99, 17percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.53 kg | Stage #1: With ethyloxirane; triphenylphosphine In ethyl acetate at 0 - 30℃; for 24 h; Large scale Stage #2: With ethyloxirane; 2,6-di-tert-butyl-4-methyl-phenol In isopropyl alcohol for 30 h; Reflux; Inert atmosphere; Large scale |
The concentrated solution of Example 6 was added dropwise to a solution of triphenylphosphine (11.8 kg) and 1,2-epoxybutane (130 g) in ethyl acetate (44 kg) at 0 to 30 ° C., and the reaction mixture was added dropwise at the same temperature And the mixture was stirred for 24 hours. The precipitated solid was collected by filtration and the wet crystals were dissolved in methylene chloride (39 kg). The obtained solution was added dropwise to ethyl acetate (305 kg) while stirring, and solid precipitation was confirmed. The precipitated solid was collected by filtration and dried in vacuo to give the title compound (3.95 kg, purity 87.5percent (trans form), 5.8percent (cis form)) as a white solid. The purity of the product was determined by high performance liquid chromatography (column: YMC-PAC ODS-A manufactured by YMC and mobile phase: acetonitrile with 0.1percent trifluoroacetic acid / 0.1percent aqueous trifluoroacetic acid = 5-95 / 45 to 5). 2,7-dimethylocta-2,4,6-triene-1,8-dialdehyde (0.484 kg), the compound of Example 7 (1) (3.90 kg), 2,6-di-t-butyl-p-cresol (32.5 g) and 1,2-epoxybutane (1.9 kg) were suspended in 2-propanol (15 kg) and the suspension was heated under reflux for 30 hours under a nitrogen atmosphere. The reaction mixture was cooled to -5 to 5 ° C. and stirred for 1 hour, and the precipitated solid was collected by filtration to give the title compound (1.53 kg, yield 86.9percent, purity 98.8percent, optical purity 97. 9percent ee) as a deep violet solid. The purity of the product was determined by high performance liquid chromatography (column: Triart C 18 ExRS Plus manufactured by YMC and mobile phase: acetonitrile with 0.025percent trifluoroacetic acid / 0.025percent aqueous trifluoroacetic acid = 30 to 98 / 2), respectively. The optical purity of the product was determined using high performance liquid chromatography (column: YMC CHIRAL Cellulose-SB manufactured by YMC and mobile phase: hexane / tetrahydrofuran = 85/15) |