4,5'-retro-b,b-Carotene-3,3'-dione, 4',5'-didehydro-

Base Information

• Chemical Name: 4,5'-retro-b,b-Carotene-3,3'-dione, 4',5'-didehydro-
• CAS No.: 116-30-3
• Molecular Formula: C40H50 O2
• Molecular Weight: 562.836
• Mol file: 116-30-3.mol

Synonyms:Rhodoxanthin(6CI,7CI); retro-b-Carotene-3,3'-dione,4',5'-didehydro-, all-trans- (8CI); 4,7'-retro-b,e-Carotene-3,3'-dione; E 161f; Rhodoxanthin, all-trans-;all-trans-Rhodoxanthin

Chemical Property of 4,5'-retro-b,b-Carotene-3,3'-dione, 4',5'-didehydro-

Chemical Property:

• Vapor Pressure: 1.46E-20mmHg at 25°C
• Melting Point: 219° (evacuated tube)
• Boiling Point: 719.7°Cat760mmHg
• Flash Point: 254.8°C
• PSA: 34.14000
• Density: 1.011g/cm³
• LogP: 10.73980

Purity/Quality:

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

RHODOXANTHIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Coloring material for food, beverages, pharmaceuticals and cosmetics. Rhodoxanthin is an antioxidant β-carotene (C184250) that has the potential to lower the risk of chronic diseases and combat vitamin A deficiency.

Technology Process of 4,5'-retro-b,b-Carotene-3,3'-dione, 4',5'-didehydro-

There total 11 articles about 4,5'-retro-b,b-Carotene-3,3'-dione, 4',5'-didehydro- 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:

5-(1-methoxy-1-methylethoxy)-3-methyl-3E-penten-1-yne (80713-62-8) → 4',5'-didehydro-4,5'-retro-β,β-carotene-3,3'-dione (116-30-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 62.0 g / LiNH₂ / liquid ammonia; diethyl ether / 2.5 h / -40 °C

2: 3N H₂SO₄ / acetone / 0.25 h / 0 °C

3: 81.3 percent / Zn, NaCN / propan-1-ol; H₂O / 5 h / Ambient temperature

4: 37percent HCl / CH₂Cl₂ / 0.25 h / 0 °C

5: CH₂Cl₂ / 18 h / Ambient temperature

6: 1.)CH₃ONa / 1.) CH₂Cl₂, CH₃OH, -20 deg C, 2 h then 0 deg C, 2 h, 2.) CH₃OH, reflux, 18 h

7: 1.) 1N KOH, air / 1.) pyridine, ethanol, 0 deg C, 30 min then R_.T_., 1.5 h, 2.) water, reflux, 48 h

With hydrogenchloride; potassium hydroxide; lithium amide; air; sulfuric acid; sodium cyanide; sodium methylate; zinc; In propan-1-ol; diethyl ether; dichloromethane; ammonia; water; acetone;

DOI:10.1002/hlca.19820650328

Reference yield:

4-((1E,3E)-5-Chloro-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-2-enone (83020-84-2) → 4',5'-didehydro-4,5'-retro-β,β-carotene-3,3'-dione (116-30-3)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂ / 18 h / Ambient temperature

2: 1.)CH₃ONa / 1.) CH₂Cl₂, CH₃OH, -20 deg C, 2 h then 0 deg C, 2 h, 2.) CH₃OH, reflux, 18 h

3: 1.) 1N KOH, air / 1.) pyridine, ethanol, 0 deg C, 30 min then R_.T_., 1.5 h, 2.) water, reflux, 48 h

With potassium hydroxide; air; sodium methylate; In dichloromethane;

DOI:10.1002/hlca.19820650328

Reference yield:

(1'E,3'E)-4-(5'-hydroxy-3'-methyl-1',3'-pentadienyl)-3,5,5-trimethyl-2-cyclohexen-1-on (83020-77-3) → 4',5'-didehydro-4,5'-retro-β,β-carotene-3,3'-dione (116-30-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 37percent HCl / CH₂Cl₂ / 0.25 h / 0 °C

2: CH₂Cl₂ / 18 h / Ambient temperature

3: 1.)CH₃ONa / 1.) CH₂Cl₂, CH₃OH, -20 deg C, 2 h then 0 deg C, 2 h, 2.) CH₃OH, reflux, 18 h

4: 1.) 1N KOH, air / 1.) pyridine, ethanol, 0 deg C, 30 min then R_.T_., 1.5 h, 2.) water, reflux, 48 h

With hydrogenchloride; potassium hydroxide; air; sodium methylate; In dichloromethane;

DOI:10.1002/hlca.19820650328

upstream raw materials:

3,7,12,16-tetramethyl-1,18-bis(2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-1,3,5,7,9,11,13,15,17-octadecanonaene

5-(1-methoxy-1-methylethoxy)-3-methyl-3E-penten-1-yne

<(2'E,4'E)-5'-(2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3'-methyl-2',4'-pentadienyl>triphenylphosphonium chloride

4-((1E,3E)-5-Chloro-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-2-enone

Downstream raw materials:

zeaxanthin

lutein

(3R,3'S,6'R)-lutein

eschscholtzxanthin

Refernces