Adonirubin

Base Information

• Chemical Name: Adonirubin
• CAS No.: 4418-72-8
• Molecular Formula: C₄₀H₅₂O₃
• Molecular Weight: 580.851
• UNII: HFX9MQ934U
• Nikkaji Number: J661.607K
• Mol file: 4418-72-8.mol

Synonyms:adonirubin

Chemical Property of Adonirubin

Chemical Property:

• XLogP3: 10.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 580.39164552
• Heavy Atom Count: 43
• Complexity: 1420

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(CCC1=O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(C(=O)C(CC2(C)C)O)C)C)C
• Isomeric SMILES: CC1=C(C(CCC1=O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C2=C(C(=O)C(CC2(C)C)O)C)/C)/C

Technology Process of Adonirubin

There total 7 articles about Adonirubin 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: 80.0%

4-oxo-β-apo-12’-carotenal (65861-49-6) + [(4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium bromide → 3-hydroxy-β,β-caroten-4,4'-dione (4418-72-8)

Guidance literature:

With ethyloxirane; for 16h; Heating;

DOI:10.1002/hlca.19810640754

Reference yield:

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) → 3-hydroxy-β,β-caroten-4,4'-dione (4418-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / triethyl orthoformate, p-toluenesulfonic acid / 15 h / Ambient temperature

2: 37 percent / 25percent HCl / CH₂Cl₂; methanol / 0.03 h / Ambient temperature

3: 1,2-epoxybutane / 16 h / Heating

4: 3N H₂SO₄ / tetrahydrofuran / 0.17 h / Ambient temperature

5: 80 percent / 1,2-epoxybutane / 16 h / Heating

With ethyloxirane; hydrogenchloride; sulfuric acid; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/hlca.19810640754

Reference yield:

7-(5,5-Dimethyl-1,3-dioxan-2-yl)-2,7-dimethyl-2,4,6-octatrienal (80713-45-7) → 3-hydroxy-β,β-caroten-4,4'-dione (4418-72-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,2-epoxybutane / 16 h / Heating

2: 3N H₂SO₄ / tetrahydrofuran / 0.17 h / Ambient temperature

3: 80 percent / 1,2-epoxybutane / 16 h / Heating

With ethyloxirane; sulfuric acid; In tetrahydrofuran;

DOI:10.1002/hlca.19810640754

upstream raw materials:

4-oxo-β-apo-12’-carotenal

β,β-Caroten-3,4,4'-triol

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

7-(5,5-Dimethyl-1,3-dioxan-2-yl)-2,7-dimethyl-2,4,6-octatrienal

Downstream raw materials:

(3S)-3-Hydroxy-β,β-carotin-4,4'-dion

Refernces

• 1、 Cooper,Davis,Leftwick,Price,Weedon. "Carotenoids and related compounds. Part XXXII. Synthesis of astaxanthin, phoenicoxanthin, hydroxyechinenone, and the corresponding diosphenols.". . p. 2195 - 2204. Retrieved 2007/10/07.