Violaxanthin

Base Information

• Chemical Name: Violaxanthin
• CAS No.: 126-29-4
• Molecular Formula: C40H56 O4
• Molecular Weight: 600.882
• Hs Code.: 29419090
• UNII: 51C926029A
• DSSTox Substance ID: DTXSID901016934
• Nikkaji Number: J387.832E,J661.001C,J8.626F
• Wikipedia: Violaxanthin
• Wikidata: Q607883
• Metabolomics Workbench ID: 29003
• Mol file: 126-29-4.mol

Synonyms:5,6:5',6'-diepoxy-5,5',6,6'- tetrahydro-beta-carotene-3,3'-diol;violaxanthin;zeaxanthin diepoxide

Chemical Property of Violaxanthin

Chemical Property:

• Vapor Pressure: 5.01E-23mmHg at 25°C
• Melting Point: 200°
• Refractive Index: 1.4760 (estimate)
• Boiling Point: 705.8°Cat760mmHg
• PKA: 14.56±0.70(Predicted)
• Flash Point: 380.7°C
• PSA: 65.52000
• Density: 1.104g/cm³
• LogP: 8.96980
• Storage Temp.: -20°C
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 9.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 600.41786026
• Heavy Atom Count: 44
• Complexity: 1270

Purity/Quality:

98%,99%, ^*data from raw suppliers

Violoxanthin - 0.897 mg/L solution in ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC=CC=C(C)C=CC=C(C)C=CC12C(CC(CC1(O2)C)O)(C)C)C=CC=C(C)C=CC34C(CC(CC3(O4)C)O)(C)C
• Isomeric SMILES: C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@@]12O[C@@]1(C[C@H](CC2(C)C)O)C)/C)/C)/C=C/C=C(/C=C/[C@@]34O[C@@]3(C[C@H](CC4(C)C)O)C)\C
• Uses: 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. 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.

Technology Process of Violaxanthin

There total 46 articles about Violaxanthin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 49.0%

C21H30O2 → Violaxanthin (126-29-4)

Guidance literature:

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;

DOI:10.1039/b915390j

Reference yield:

4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol (23069-07-0) → Violaxanthin (126-29-4)

Guidance literature:

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.

With methanol; tert.-butylhydroperoxide; manganese(IV) oxide; Montmorillonite; oxalyl dichloride; Ti(i-PrO); potassium tert-butylate; water; diisobutylaluminium hydride; magnesium sulfate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene;

DOI:10.1002/hlca.19880710502

Reference yield:

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

Guidance literature:

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.

With methanol; tert.-butylhydroperoxide; manganese(IV) oxide; Montmorillonite; lithium aluminium tetrahydride; oxalyl dichloride; Ti(i-PrO); potassium tert-butylate; water; diisobutylaluminium hydride; magnesium sulfate; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; zinc(II) chloride; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; n-heptane; dichloromethane; ethyl acetate; toluene; benzene;

DOI:10.1002/hlca.19880710502

upstream raw materials:

(15Z)-Violaxanthin

C₄₆H₄₂P₂

(1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal

13-cis-violaxanthin

Downstream raw materials:

auroxanthin

all-trans-mutatoxanthin

auroxanthin

(1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal

Refernces

• 1、 Molnar, Peter,Szabolcs, Jozsef,Radics, Lajos. "NATURALLY OCURING DI-CIS-VIOLAXANTHINS FROM VIOLA TRICOLOR: ISOLATION AND IDENTIFICATION BY 1H NMR SPECTROSCOPY OF FOUR DI-CIS-ISOMERS". . p. 195 - 200. Retrieved 1986.
• 2、 Molnar, Peter,Kortvelyesi, Tarnas,Matus, Zoltan,Szabolca, Jozsef. "Kinetic Studies on the Thermal (Z/E)-Isomerization of C40-Carotenoids". . p. 801 - 841. Retrieved 2007/10/03.