126-29-4

Basic information

• Product Name: VIOLAXANTHIN
• Synonyms: ZEAXANTHIN DIEPOXIDE;VIOLAXANTHIN;(1R,3S,6S)-6-[18-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]hept-6-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol;Violoxanthin;(3S,3'S,5R,5'R,6S,6'S,9E)-5,6:5',6'-Bisepoxy-5,5',6,6'-tetrahydro-β,β-carotene-3,3'-diol;5α,6α:5'α,6'α-Bisoxy-5,5',6,6'-tetrahydro-β,β-carotene-3β,3'β-diol;5α,6α:5'α,6'α-Bisoxy-5,5',6,6'-tetrahydro-β,β-carotene-3β,3β'-diol;all-trans-Violaxanthin
• CAS NO: 126-29-4
• Molecular Formula: C₄₀H₅₆O₄
• Molecular Weight: 600.87
• Product Categories: Carotenoids
• Mol File: 126-29-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 200°
• Boiling Point: 570.8°C (rough estimate)
• Flash Point: 380.7°C
• Appearance: /
• Density: 0.9826 (rough estimate)
• Vapor Pressure: 5.01E-23mmHg at 25°C
• Refractive Index: 1.4760 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform, Ethyl Acetate
• PKA: 14.56±0.70(Predicted)
• BRN: 101269
• CAS DataBase Reference: VIOLAXANTHIN(CAS DataBase Reference)
• NIST Chemistry Reference: VIOLAXANTHIN(126-29-4)
• EPA Substance Registry System: VIOLAXANTHIN(126-29-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 126-29-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 126-29-4 differently. You can refer to the following data:
1. trans-Violaxanthin, is a Carotenoid dye. It is a natural xanthophyll pigment with an orange color found in a variety of plants including pansies. It is approved to be used as a food additive and food coloring.
2. Violaxanthin has been used as a standard/control in high-pressure liquid chromatography (HPLC) analysis of pigment extracts to confirm the high-level astaxanthin accumulation suspected from the visual phenotype of?Nt-AXT plants.

General Description

Violaxanthins are natural pigmented constituents or carotenoids present in most fruits and vegetables.

Biochem/physiol Actions

Violaxanthin is a carotene epoxide that is a precursor to capsanthin. It is one of three xanthophylls involved in the evolution of plastids of green plants (oxygen evolution) and participating in photo-induced interconversions known as the violaxanthin cycle. The cleavage of 9-cis-epoxycarotenoids (violaxanthin) to xanthoxin is the key regulatory step of abscisic acid biosynthesis.

Purification Methods

Also purify it by column chromatography, and the purity is checked by TLC (see -carotene). It has at 415, 440 and 469nm. [Kuhn & Winterstein Ber 64 326 1931, Karrer et al. max Helv Chim Acta 14 1044 1931, Absolute Config: Bartlett et al. J Chem Soc (C) 2527 1969, Beilstein 19 III/IV 1139.]

InChI:InChI=1/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1

Synthetic route

C21H30O2 → Violaxanthin (126-29-4)

Conditions	Yield
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 (126-29-4, 1263-54-3, 24502-89-4, 24620-97-1, 25493-67-8, 26917-74-8, 26917-75-9, 26927-07-1, 29246-93-3, 75715-58-1, 80629-23-8, 80629-24-9, 101627-32-1, 101627-33-2, 101627-34-3, 101627-35-4, 113667-07-5, 115182-31-5, 116126-19-3, 122407-49-2, 122407-51-6, 147383-89-9, 147383-90-2, 147383-91-3) → Violaxanthin (126-29-4) + C40H56O4 + C40H56O4

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In n-heptane for 1.5h; Heating; Irradiation; Yield given. Yields of byproduct given;

C46H42P2 (39776-40-4) + (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal (28874-44-4) → Violaxanthin (126-29-4) + C40H56O4 + C40H56O4

Conditions	Yield
In methanol 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t.; Yield given. Yields of byproduct given;

di-cis-neoviolaxanthin C → 9-cis-violaxanthin (26927-07-1) + Violaxanthin (126-29-4)

Conditions	Yield
In benzene for 2h; Heating; stereomutation; further violaxanthins; iodine catalyst;

13-cis-violaxanthin (75715-58-1) → Violaxanthin (126-29-4) + central-cis-violaxanthin (24620-97-1)

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;

central-cis-violaxanthin (24620-97-1) → Violaxanthin (126-29-4) + 13-cis-violaxanthin (75715-58-1)

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 (115406-45-6, 16638-61-2) → (3S,5S,6R,3'R)-antheraxanthin (25494-45-5) + violaxanthin B (80629-24-9) + violaxanthin A (80629-23-8) + Violaxanthin (126-29-4)

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 (23069-07-0) → Violaxanthin (126-29-4)

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

4-methyl-pent-3-en-2-one (141-79-7) + sodium → Violaxanthin (126-29-4)

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 (23069-06-9) → Violaxanthin (126-29-4)

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

ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate (23068-96-4) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) CH(OEt)3; 2.) TsOH*H2O / 1.) H2SO4, 12 deg C, 1440 min; 2.) Et2O, H2O, 5 min, r.t. 2: LiAlH4 / various solvent(s) / 2.5 h / 55 °C 3: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 4: 91 percent / pyridine / 4 h / 0 °C 5: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 7: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 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
Multi-step reaction with 13 steps 1: 1.) CH(OEt)3; 2.) TsOH*H2O / 1.) H2SO4, 12 deg C, 1440 min; 2.) Et2O, H2O, 5 min, r.t. 2: LiAlH4 / various solvent(s) / 2.5 h / 55 °C 3: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 4: 91 percent / pyridine / 4 h / 0 °C 5: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 7: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 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: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 12: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 13: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme
Multi-step reaction with 10 steps 1: 1.) CH(OEt)3; 2.) TsOH*H2O / 1.) H2SO4, 12 deg C, 1440 min; 2.) Et2O, H2O, 5 min, r.t. 2: LiAlH4 / various solvent(s) / 2.5 h / 55 °C 3: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 4: 91 percent / pyridine / 4 h / 0 °C 5: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 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

(-)-(1S,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-carbaldehyd (122346-85-4, 132340-85-3, 142563-00-6) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 15.86 g / tetrahydrofuran 2: MgSO4, H2O, montmorillonite / toluene / 0.04 h 3: DIBAH, H2O, MeOH / diethyl ether; hexane / 3 h / Ambient temperature 4: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 5: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 7 steps 1: 15.86 g / tetrahydrofuran 2: MgSO4, H2O, montmorillonite / toluene / 0.04 h 3: DIBAH, H2O, MeOH / diethyl ether; hexane / 3 h / Ambient temperature 4: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 5: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 6: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 7: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

C18H30O6P2 → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 2: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 3: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal (28874-44-4) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 2: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 3: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(+)-(1R,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-methanol (122346-75-2, 122407-34-5, 142562-99-0) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 8 steps 1: 91 percent / pyridine / 4 h / 0 °C 2: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 4: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 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
Multi-step reaction with 10 steps 1: 91 percent / pyridine / 4 h / 0 °C 2: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 4: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 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: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 9: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 10: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme
Multi-step reaction with 7 steps 1: 91 percent / pyridine / 4 h / 0 °C 2: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 4: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 5: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 6: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 7: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme

15,15'-Didehydroviolaxanthin (122346-90-1) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 2: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(1'S,2'R,2E,4E)-5-(1',2'-Epoxy-2',6',6'-trimethyl-4'-oxocyclohexyl)-3-methyl-2,4-pentadiensaeure-methylester (122346-88-7) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: DIBAH, H2O, MeOH / diethyl ether; hexane / 3 h / Ambient temperature 2: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 3: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 5 steps 1: DIBAH, H2O, MeOH / diethyl ether; hexane / 3 h / Ambient temperature 2: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 3: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 4: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 5: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester (122346-77-4) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 6 steps 2: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 3: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 4: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 5: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 6: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 8 steps 2: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 3: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 4: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 5: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 6: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 7: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 8: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme
Multi-step reaction with 5 steps 2: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 3: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 4: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 5: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme

(1R,2R,4S)-Essigsaeure-(1,2-epoxy-4-hydroxy-2,6,6-trimethylcyclohexan-1-methyl)ester → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: 93 percent / pyridine / 12 h / 4 °C 2: 96 percent / 5percent KOH / methanol 3: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 4: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 5: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 6: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 7: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 9 steps 1: 93 percent / pyridine / 12 h / 4 °C 2: 96 percent / 5percent KOH / methanol 3: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 4: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 5: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 6: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 7: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 8: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 9: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(1R,2R,4S)-1,2-Epoxy-4-pivaloyloxy-2,6,6-trimethylcyclohexan-1-methanol (122346-81-0) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 2: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 3: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 4: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 5: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 7 steps 1: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 2: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 3: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 4: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 5: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 6: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 7: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(2E,4E)-5-[(1'S,2'R,4'S)-4'-hydroxy-1',2'-epoxy-2',6',6'-trimethylcyclohexa-1'-yl]-3-methylpenta-2,4-diene-1-ol (118205-56-4) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 2: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 4 steps 1: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 2: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 3: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 4: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(1R,2R)-Essigsaeure-<1,2-epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-methyl>ester → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 3: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 4: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 5: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 6: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 7: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 9 steps 1: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 3: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 4: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 5: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 6: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 7: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 8: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 9: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme
Multi-step reaction with 6 steps 1: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 3: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 4: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 5: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 6: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme

(1R,2R,4S)-1,2-Epoxy-4-pivaloyloxy-2,6,6-trimethylcyclohexan-1-carbaldehyd (122346-82-1) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 2: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 3: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 4: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 6 steps 1: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 2: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 3: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 4: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 5: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 6: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(1R,2R,4S)-Essigsaeure-(1,2-epoxy-4-pivaloyloxy-2,6,6-trimethylcyclohexan-1-methyl)ester (122346-80-9) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: 96 percent / 5percent KOH / methanol 2: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 3: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 4: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 5: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 6: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 8 steps 1: 96 percent / 5percent KOH / methanol 2: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 3: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 4: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 5: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 6: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 7: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 8: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(1'S,2'R,2E,4E)-5-<1',2'-Epoxy-4',4'-(ethylendioxy)-2',6',6'-trimethylcyclohexyl>-3-methylpenta-2,4-diensaeure-methylester → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: MgSO4, H2O, montmorillonite / toluene / 0.04 h 2: DIBAH, H2O, MeOH / diethyl ether; hexane / 3 h / Ambient temperature 3: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 4: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 6 steps 1: MgSO4, H2O, montmorillonite / toluene / 0.04 h 2: DIBAH, H2O, MeOH / diethyl ether; hexane / 3 h / Ambient temperature 3: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 4: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 5: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 6: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

(1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-pivaloyloxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester (122346-84-3) → Violaxanthin (126-29-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 2: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 3: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t. View Scheme
Multi-step reaction with 5 steps 1: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 2: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 3: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 4: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h 5: 0.1percent (i-Pr)2EtN / heptane / 1.5 h / Heating; Irradiation View Scheme

Violaxanthin (126-29-4) → Violadion

Conditions	Yield
With acetic anhydride In dimethyl sulfoxide Ambient temperature;	60%

Violaxanthin (126-29-4) + acetic anhydride (108-24-7) → (3S,5R,6S,3'S,5'R,6'S)-violaxanthin diacetate (20584-58-1, 62839-94-5, 75172-74-6, 106357-50-0, 122407-50-5)

Conditions	Yield
With pyridine

Violaxanthin (126-29-4) → 9-cis-violaxanthin (26927-07-1)

Conditions	Yield
With hexane; iodine Irradiation;
Photoisomerization;

Violaxanthin (126-29-4) → auroxanthin (27785-15-5)

Conditions	Yield
With ethanol; acetic acid
bei der Chromatographie an Kieselgel oder Kieselgur;
With hydrogenchloride In chloroform

Violaxanthin (126-29-4) → (6S,7aR)-2-[(2E,4E,6E,8E,10E,12E,14E)-17-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-6-ol (1912-50-1, 29363-89-1, 29558-14-3, 55963-84-3, 68366-25-6, 81646-18-6, 95119-74-7, 95119-75-8, 95119-76-9, 95119-77-0, 115182-32-6, 123618-86-0)

Conditions	Yield
With pyridine; benzoyl chloride Behandeln des nach Abtrennung von Di-O-benzoyl-violaxanthin erhaltenen Reaktionsprodukts mit Natriummaethylat in Aethanol;
Chromatographie an Kieselgel;

Violaxanthin (126-29-4) + 4-chlorobenzoyl chloride (586-75-4) → violaxanthin di-p-bromobenzoate

Conditions	Yield
With pyridine at 0℃; for 1.5h;

Violaxanthin (126-29-4) → (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal (28874-44-4) + 5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al (62777-81-5) + 5,6-epoxy-3-hydroxy-5,6-dihydro-10'-apo-β-caroten-10'-al (17237-68-2)

Conditions	Yield
With zinc(II) permanganate In acetone for 1h; Ambient temperature;

Violaxanthin (126-29-4) → (3S,5R,6E,6'E)-5,6-dihydro-6,5'-retro-β,β-carotene-3,5,3',5'-tetrol

Conditions	Yield
chromoplasts from Narcissus pseudonarcissus, NAD(P)H, protoporphyrin IX;

Violaxanthin (126-29-4) → 13-cis-violaxanthin (75715-58-1) + central-cis-violaxanthin (24620-97-1)

Conditions	Yield
In pyridine at 73.6 - 93.8℃; Kinetics; Equilibrium constant; Thermodynamic data; other C40-carotenoids, other solvents, var. temp.; EA, ΔH, ΔS, ΔG;

Violaxanthin (126-29-4) → auroxanthin (27785-15-5) + (3S,5R,8Ξ,3'R)-5,8-epoxy-5,8-dihydro-β,β-carotene-3,3'-diol;(3R,3'R)-β,β-carotene-3,3'-diol

Conditions	Yield
With hydrogenchloride; methanol

Violaxanthin (126-29-4) + hexane (110-54-3) + iodine (7553-56-2) → 9-cis-violaxanthine

Conditions	Yield
Isomerisierung.Irradiation;

Violaxanthin (126-29-4) → all-trans-mutatoxanthin (31661-06-0) + auroxanthine

Conditions	Yield
With hydrogenchloride; methanol (3S,5R,8Ξ,3'R)-5,8-epoxy-5,8-dihydro-β,β-carotene-3,3'-diol;

Violaxanthin (126-29-4) → luteoxanthin + auroxanthine

Conditions	Yield
Isomerisierung, beim Chromatographieren an Kieselgel;

Violaxanthin (126-29-4) + hydrogenchloride (7647-01-0) + methanol (67-56-1) → auroxanthine + mutatoxanthine + (3R,3'R)-β,β-carotene-3,3'-diol

Violaxanthin (126-29-4) → 9-cis-violaxanthin (26927-07-1) + 13-cis-violaxanthin (75715-58-1) + /PBNZK047-1730/ + /PBNZK047-1740/

Conditions	Yield
With diphenyl diselenide In benzene for 27h; Irradiation; Further byproducts given;

Violaxanthin (126-29-4) + diethyl ether (60-29-7) + lithium alanate → zeaxanthin

Violaxanthin (126-29-4) → 9-cis-violaxanthin (26927-07-1) + 13-cis-violaxanthin (75715-58-1) + /PBNZK047-1730/ + /PBNZK047-1735/

Conditions	Yield
With diphenyl diselenide In benzene for 3h; Irradiation; Further byproducts given;

Violaxanthin (126-29-4) → all-trans-mutatoxanthin (31661-06-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: chromoplasts from Narcissus pseudonarcissus, NAD(P)H, protoporphyrin IX 2: 100 percent Spectr. / CDCl3 / 96 h View Scheme

Violaxanthin (126-29-4) → 8-p-bromobenzoyloxy-5,6-epoxy-β-cyclocitral

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 1.5 h / 0 °C 2: ozone / ethyl acetate / 0.15 h / -78 °C View Scheme

Violaxanthin (126-29-4) → trans-4-<(1S,2R,4R)-4-(p-bromobenzoyloxy)-1,2-epoxy-2,6,6-trimethylcyclohexyl>but-3-en-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 1.5 h / 0 °C 2: ozone / ethyl acetate / 0.15 h / -78 °C View Scheme

Upstream product

• 126-29-4 (15Z)-Violaxanthin 
• 23068-96-4 ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate 
• 122346-84-3 (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-pivaloyloxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester 
• 122346-80-9 (1R,2R,4S)-Essigsaeure-(1,2-epoxy-4-pivaloyloxy-2,6,6-trimethylcyclohexan-1-methyl)ester 
• 122346-82-1 (1R,2R,4S)-1,2-Epoxy-4-pivaloyloxy-2,6,6-trimethylcyclohexan-1-carbaldehyd 
• 118205-56-4 (2E,4E)-5-[(1'S,2'R,4'S)-4'-hydroxy-1',2'-epoxy-2',6',6'-trimethylcyclohexa-1'-yl]-3-methylpenta-2,4-diene-1-ol 
• 122346-81-0 (1R,2R,4S)-1,2-Epoxy-4-pivaloyloxy-2,6,6-trimethylcyclohexan-1-methanol 
• 122346-77-4 (1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester 
• 122346-88-7 (1'S,2'R,2E,4E)-5-(1',2'-Epoxy-2',6',6'-trimethyl-4'-oxocyclohexyl)-3-methyl-2,4-pentadiensaeure-methylester 
• 122346-75-2 (+)-(1R,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-methanol 
• 28874-44-4 (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal 
• 122346-85-4 (-)-(1S,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-carbaldehyd 
• 23069-06-9 4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-carbonsaeure-ethylester 
• 141-79-7 4-methyl-pent-3-en-2-one 

Downstream Products

• 27785-15-5 auroxanthin 
• 31661-06-0 all-trans-mutatoxanthin 
• 11011-41-9 auroxanthin 
• 28874-44-4 (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal 
• 62777-81-5 5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al 
• 17237-68-2 5,6-epoxy-3-hydroxy-5,6-dihydro-10'-apo-β-caroten-10'-al 

Related news

Investigating the interaction between the VIOLAXANTHIN (cas 126-29-4) cycle enzyme zeaxanthin epoxidase and the thylakoid membrane09/29/2019

In the present study the interaction between the violaxanthin cycle enzyme zeaxanthin epoxidase (ZEP) and the thylakoid membrane was investigated. Isolated, active thylakoid membranes of spinach (Spinacia oleracea L.) were subjected to different salt and detergent treatments that are generally u...detailed

Temperature-induced isomerization of VIOLAXANTHIN (cas 126-29-4) in organic solvents and in light-harvesting complex II09/28/2019

Three main xanthophyll pigments are bound to the major photosynthetic pigment-protein complex of Photosystem II (LHCII): lutein, neoxanthin and violaxanthin. Chromatographic analysis of the xanthophyll fraction of LHCII reveals that lutein appears mainly in the all-trans conformation, neoxanthin...detailed

Non-photochemical fluorescence quenching in Chromera velia is enabled by fast VIOLAXANTHIN (cas 126-29-4) de-epoxidation10/01/2019

Non-photochemical quenching (NPQ) is a mechanism protecting photosynthetic organisms against excessive irradiation. Here, we analyze a unique NPQ mechanism in the alga Chromera velia, a recently discovered close relative of apicomplexan parasites. NPQ in C. velia is enabled by an operative and f...detailed

Membrane curvature stress controls the maximal conversion of VIOLAXANTHIN (cas 126-29-4) to zeaxanthin in the VIOLAXANTHIN (cas 126-29-4) cycle—influence of α-tocopherol, cetylethers, linolenic acid, and temperature09/27/2019

Zeaxanthin, an important component in protection against overexcitation in higher plants, is formed from violaxanthin by the enzyme violaxanthin de-epoxidase. We have investigated factors that may control the maximal degree of conversion in the violaxanthin cycle. The conversion of violaxanthin ...detailed

Geometrical isomers of VIOLAXANTHIN (cas 126-29-4) in orange juice09/26/2019

The geometrical isomers of carotenoids are now attracting considerable interest, due in part to the fact that they are known to behave differently in terms of susceptibility to oxidation, vitamin A activity and bioavailability. The study of such isomers has been facilitated by the development of...detailed

Characterization of cucumber VIOLAXANTHIN (cas 126-29-4) de-epoxidase gene promoter in Arabidopsis09/24/2019

Violaxanthin de-epoxidase (VDE) activates the dissipation of excessive light energy as heat and protects the photosynthetic apparatus from photo-damage. Here we quantitatively analyzed the expression characteristics of cucumber violaxanthin de-epoxidase (CsVDE) promoter using the 1983 bp upstrea...detailed

The xanthophyll cycle pigments, VIOLAXANTHIN (cas 126-29-4) and zeaxanthin, modulate molecular organization of the photosynthetic antenna complex LHCII09/10/2019

The effect of violaxanthin and zeaxanthin, two main carotenoids of the xanthophyll cycle, on molecular organization of LHCII, the principal photosynthetic antenna complex of plants, was studied in a model system based on lipid-protein membranes, by means of analysis of 77 K chlorophyll a fluores...detailed

Relevant articles and documents

Olefin metathesis in carotenoid synthesis

Olefin metathesis is a powerful and widely applicable synthetic method for carbon-carbon double bond formation. However, its application to the synthesis of conjugating polyene chains has been very limited because of possible undesired side reactions. We attempted to apply this method to the synthesis of symmetrical carotenoids. In this paper, the syntheses of violaxanthin and mimulaxanthin are described using the olefin metathesis protocol.

Preparation and (E/Z)-Isomerization of the Diastereoisomers of Violaxanthin

Violaxanthin A (=(all-E,3S,5S,6R,3′S,5′S,6′ R)-5,6:5′,6′-diepoxy-5,6,5′,6′-tetrahydro-β, β-carotene-3,3′-diol = syn,syn-violaxanthin; 5) and violaxanthin B (=(all-E,3S,5S,6R,3′S,5′R,6′S)-5,6:5′, 6′-diepoxy-5,6,5′,6′-tetrahydro-β,β-carotene-3, 3′-diol = syn,anti-violaxanthin; 6) were prepared by epoxidation of zeaxanthin diacetate (1) with monoperphthalic acid. Violaxanthins 5 and 6 were submitted to thermal isomerization and I2-catalyzed photoisomerization. The structure of the main products, i.e., (9Z)-5, (13Z)-5, (9Z)-6, (9′Z)-6, (13Z)-6, and (13′Z)-6, was determined by their UV/VIS, CD, 1H-NMR, 13C-NMR, and mass spectra.

Syntheses of Enantiomerically Pure Violaxanthins and Related Compounds

The epoxides 16 and ent-16, prepared by Sharpless-Katsuki oxidation of 15 in excellent yield and very high enantiomeric purity, were used as synthons for the preparation of (+)-(S)-didehydrovomifoliol (45), (+)-(6S,7E,9E)-abscisic ester 46, (+)-(6S,7E,9Z)-abscisic ester 47, (-)-(3S,7E,9E)-xanthoxin (49), (-)-(3R,7E,9E)-xanthoxin (50), (3S,5R,6S,3'S,5'R,6'S,all-E)-violaxanthin (1), (3R,5R,6S,3'R,5'R,6'S,all-E)-violaxanthin (55) and their (9Z) (see 53, 57), (13Z) (see 54, 58), and (15Z) (see 60) isomers.The novel violadione (61) was prepared from 1 by oxidation with DMSO/Ac2O.By base treatment, 61 was converted into violadienedione (62), a potential precursor of carotenoids with phenolic end groups.