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CAS No.: | 126-29-4 |
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Name: | VIOLAXANTHIN |
Article Data: | 7 |
Molecular Structure: | |
Formula: | C40H56 O4 |
Molecular Weight: | 600.882 |
Synonyms: | b-Carotene-3,3'-diol,5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro- (6CI); b-Carotene-3,3'-diol,5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, all-trans- (8CI);7-Oxabicyclo[4.1.0]heptane, b,b-carotene-3,3'-diol deriv.; COrange 15; E 161e; Violaxanthin; Violaxanthin, all-trans-; all-E-Violaxanthin;all-trans-Violaxanthin; anti,anti-Violaxanthin; trans-Violaxanthin |
Density: | 1.104g/cm3 |
Melting Point: | 200° |
Boiling Point: | 705.8°Cat760mmHg |
Flash Point: | 380.7°C |
PSA: | 65.52000 |
LogP: | 8.96980 |
Violaxanthin
Conditions | Yield |
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With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 60℃; for 0.166667h; | 49% |
(15Z)-Violaxanthin
A
Violaxanthin
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In n-heptane for 1.5h; Heating; Irradiation; Yield given. Yields of byproduct given; |
C46H42P2
(1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal
A
Violaxanthin
Conditions | Yield |
---|---|
In methanol 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t.; Yield given. Yields of byproduct given; |
Conditions | Yield |
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In benzene for 2h; Heating; stereomutation; further violaxanthins; iodine catalyst; |
Conditions | Yield |
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In pyridine at 73.6 - 93.9℃; Kinetics; Equilibrium constant; Thermodynamic data; other C40-carotenoids, other solvents, var. temp.; EA, ΔH, ΔS, ΔG; |
Conditions | Yield |
---|---|
In pyridine at 73.6 - 93.9℃; Kinetics; Equilibrium constant; Thermodynamic data; other C40-carotenoids, other solvents, var. temp.; EA, ΔH, ΔS, ΔG; |
(all-E,3R,3'R)-β,β-carotene-3,3'-diol 3,3'-diacetate
A
(3S,5S,6R,3'R)-antheraxanthin
B
violaxanthin B
C
violaxanthin A
D
Violaxanthin
Conditions | Yield |
---|---|
Stage #1: (all-E,3R,3'R)-β,β-carotene-3,3'-diol 3,3'-diacetate With monoperoxyphthalic acid In diethyl ether at 20℃; for 40h; Stage #2: With potassium hydroxide In methanol Further byproducts given; | A 60 mg B 75 mg C 80 mg D 10 mg |
4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol
Violaxanthin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 2: 91 percent / pyridine / 4 h / 0 °C 3: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 5: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 6: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 7: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 8: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 9: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme | |
Multi-step reaction with 11 steps 1: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 2: 91 percent / pyridine / 4 h / 0 °C 3: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 5: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 6: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 7: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 8: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 9: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 10: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 11: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme | |
Multi-step reaction with 8 steps 1: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 2: 91 percent / pyridine / 4 h / 0 °C 3: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 5: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 6: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 7: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 8: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: 36 percent / ZnCl2 / heptane; benzene / 211 h / Heating 2: 1.) CH(OEt)3; 2.) TsOH*H2O / 1.) H2SO4, 12 deg C, 1440 min; 2.) Et2O, H2O, 5 min, r.t. 3: LiAlH4 / various solvent(s) / 2.5 h / 55 °C 4: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 5: 91 percent / pyridine / 4 h / 0 °C 6: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 8: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 9: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 10: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 11: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 12: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme | |
Multi-step reaction with 14 steps 1: 36 percent / ZnCl2 / heptane; benzene / 211 h / Heating 2: 1.) CH(OEt)3; 2.) TsOH*H2O / 1.) H2SO4, 12 deg C, 1440 min; 2.) Et2O, H2O, 5 min, r.t. 3: LiAlH4 / various solvent(s) / 2.5 h / 55 °C 4: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 5: 91 percent / pyridine / 4 h / 0 °C 6: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 8: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 9: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 10: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 11: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 12: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 13: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 14: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme | |
Multi-step reaction with 11 steps 1: 36 percent / ZnCl2 / heptane; benzene / 211 h / Heating 2: 1.) CH(OEt)3; 2.) TsOH*H2O / 1.) H2SO4, 12 deg C, 1440 min; 2.) Et2O, H2O, 5 min, r.t. 3: LiAlH4 / various solvent(s) / 2.5 h / 55 °C 4: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 5: 91 percent / pyridine / 4 h / 0 °C 6: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 8: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 9: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 10: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 11: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme |
4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-carbonsaeure-ethylester
Violaxanthin
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: LiAlH4 / various solvent(s) / 2.5 h / 55 °C 2: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 3: 91 percent / pyridine / 4 h / 0 °C 4: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 6: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 7: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 8: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 9: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 10: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme | |
Multi-step reaction with 12 steps 1: LiAlH4 / various solvent(s) / 2.5 h / 55 °C 2: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 3: 91 percent / pyridine / 4 h / 0 °C 4: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 6: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 7: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 8: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 9: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 10: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 11: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 12: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme | |
Multi-step reaction with 9 steps 1: LiAlH4 / various solvent(s) / 2.5 h / 55 °C 2: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 3: 91 percent / pyridine / 4 h / 0 °C 4: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 6: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 7: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 8: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 9: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme |