Gentianine

Base Information

• Chemical Name: Gentianine
• CAS No.: 439-89-4
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.187
• NSC Number: 606848
• UNII: C2PD310UXB
• DSSTox Substance ID: DTXSID00963141
• Nikkaji Number: J11.377H
• Wikipedia: Gentianine
• Wikidata: Q27104004
• Metabolomics Workbench ID: 51914
• ChEMBL ID: CHEMBL4753058
• Mol file: 439-89-4.mol

Synonyms:5-ethenyl-3,4-dihydro-1H-pyrano(3,4-c)pyridin-1-one;gentianine

Chemical Property of Gentianine

Chemical Property:

• Vapor Pressure: 3.52E-06mmHg at 25°C
• Melting Point: 84-86℃
• Refractive Index: 1.604
• Boiling Point: 386.5 °C at 760 mmHg
• PKA: 3.62±0.20(Predicted)
• Flash Point: 187.6 °C
• PSA: 39.19000
• Density: 1.225 g/cm³
• LogP: 1.43750
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 227

Purity/Quality:

98%Min ^*data from raw suppliers

Gentianine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1=CN=CC2=C1CCOC2=O
• Uses: Gentianine is used as an anti-inflammatory reducing the production of pro-inflammatory cytokines.

Technology Process of Gentianine

There total 4 articles about Gentianine 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: 85.0%

→ gentianine (439-89-4)

Guidance literature:

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-methyl-5-vinylnicotinic acid (99357-78-5) → gentianine (439-89-4)

Guidance literature:

With sodium hydrogencarbonate;

Reference yield:

1-oxo-5-vinyl-1H-pyrano[3,4-c]pyridine-3-carboxylic acid ethyl ester (57110-41-5) → gentianine (439-89-4)

Guidance literature:

With water; N,N-dimethyl-formamide; sodium chloride;

DOI:10.1021/jo00877a007

upstream raw materials:

formaldehyd

4-methyl-5-vinylnicotinic acid

1-oxo-5-vinyl-1H-pyrano[3,4-c]pyridine-3-carboxylic acid ethyl ester

5-ethenyl-4-methyl-3-pyridinecarbonitrile

Refernces

• 1、 Kwak, Wie-Jong,Kim, Joo-Hyon,Ryu, Keun-Ho,Cho, Yong-Baik,Jeon, Sun-Duck,Moon, Chang-Kiu. "Effects of gentianine on the production of pro-inflammatory cytokines in male Sprague-Dawley rats treated with lipopolysaccharide (LPS)". . p. 750 - 753. Retrieved 2005.