Peretinoin

Base Information

• Chemical Name: Peretinoin
• CAS No.: 81485-25-8
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.457
• European Community (EC) Number: 632-866-6
• UNII: 11ALM7A4RV
• DSSTox Substance ID: DTXSID801316826
• Nikkaji Number: J533.293A,J711.895C,J1.628.090I
• Wikidata: Q18326479
• NCI Thesaurus Code: C87202
• ChEMBL ID: CHEMBL4303228
• Mol file: 81485-25-8.mol

Synonyms:(2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid;(2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoic acid;3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoic acid;NIK-333;peretinoin

Chemical Property of Peretinoin

Chemical Property:

• Vapor Pressure: 9.42E-10mmHg at 25°C
• Boiling Point: 460.3°C at 760 mmHg
• PKA: 4.79±0.33(Predicted)
• Flash Point: 348.5°C
• PSA: 37.30000
• Density: 0.943g/cm³
• LogP: 5.99270
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 302.224580195
• Heavy Atom Count: 22
• Complexity: 496

Purity/Quality:

99%+, ^*data from raw suppliers

Peretinoin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CC=CC(=CC(=O)O)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/C=C/C(=C/C(=O)O)/C)/C)/C)C
• Recent ClinicalTrials: Study of Peretinoin for Suppressing Recurrence of HCV-positive HCC
• Recent NIPH Clinical Trials: A Study of K-333 (peretinoin) in Patients with Complete Cure of Hepatitis B Virus (HBV)-Positive Hepatocellular Carcinoma
• Uses: Peretinoin is an acyclic retinoid that may have the ability to inhibit hepatic carcinogenesis

Technology Process of Peretinoin

There total 10 articles about Peretinoin 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: 75.0%

(all-E)-3,7,11,15-tetramethyl-hexadeca-2,4,6,10,14-pentaenoic acid methyl ester (93040-99-4) → peretinoin (81485-25-8)

Guidance literature:

With potassium hydroxide; In isopropyl alcohol; at 55 - 60 ℃; for 1h;

DOI:10.1021/ja00337a042

Reference yield: 51.0%

(2E,4E,6E,10E)-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid ethyl ester (172286-90-7) → peretinoin (81485-25-8)

Guidance literature:

With potassium hydroxide; In ice-water; isopropyl alcohol;

Reference yield:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 6,10,14-trimethyl-3,5,9,13-pentadecatetraen-2-one (4004-12-0) → peretinoin (81485-25-8)

Guidance literature:

With potassium hydroxide; In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; water;

upstream raw materials:

(all-E)-3,7,11,15-tetramethyl-hexadeca-2,4,6,10,14-pentaenoic acid methyl ester

all-E 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentanenal

all-E 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentanitrile

(2E,6E,10E)-4-Hydroxy-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenenitrile

Refernces

• 1、 -. "METHOD FOR MANUFACTURING PHOSPHONOCROTONIC ACID DERIVATIVE". Paragraph 0150-0152. . Retrieved 2014/03/24.
• 2、 -. "Method of purification of polyprenyl compounds". . . Retrieved 2008/06/13.