Aurantio-obtusin

Base Information

• Chemical Name: Aurantio-obtusin
• CAS No.: 67979-25-3
• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.294
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID90218172
• Nikkaji Number: J815.992K
• Wikidata: Q27117130
• Metabolomics Workbench ID: 55560
• ChEMBL ID: CHEMBL461288
• Mol file: 67979-25-3.mol

Synonyms:aurantio-obtusin

Chemical Property of Aurantio-obtusin

Chemical Property:

• Vapor Pressure: 9.8E-15mmHg at 25°C
• Melting Point: 265-266 °C
• Refractive Index: 1.678
• Boiling Point: 594.6 °C at 760 mmHg
• PKA: 6.32±0.20(Predicted)
• Flash Point: 222.4 °C
• PSA: 113.29000
• Density: 1.51 g/cm³
• LogP: 1.90440
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 330.07395278
• Heavy Atom Count: 24
• Complexity: 521

Purity/Quality:

≥98% ^*data from raw suppliers

Aurantio-obtusin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C(=C1O)OC)C(=O)C3=C(C(=C(C=C3C2=O)O)OC)O
• Description: Aurantioobtusin is an anthraquinone originally isolated from Cassia seeds with diverse biological activities. It inhibits rat lens aldose reductase (RLAR) in vitro (IC50 = 13.6 μM). Aurantioobtusin (10 and 100 μM) activates the aryl hydrocarbon receptor (AhR) in a concentration-dependent manner. It inhibits rat platelet aggregation induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607), ADP, and collagen. Aurantioobtusin induces vasorelaxation in isolated precontracted rat mesenteric artery rings, an effect that is inhibited by the PI3K inhibitor LY290042 or inhibition of endothelial nitric oxide synthase (eNOS). It is larvicidal against A. gambiae mosquitoes (LD50 = 10 ppm).
• Uses: A compound found in herbal remedies, believed to have an effect on blood platelet aggregation and lower blood lipid count

Technology Process of Aurantio-obtusin

There total 6 articles about Aurantio-obtusin 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:

5,7-Dihydroxy-6-methoxy-[1,4]naphthoquinone → Aurantio-obtusin (67979-25-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

3: DDQ / CH₂Cl₂

4: NaOH

With sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; dichloromethane;

DOI:10.1016/S0040-4039(00)85117-5

Reference yield:

Acetic acid 4-hydroxy-3-methoxy-5,8-dioxo-5,8-dihydro-naphthalen-2-yl ester (108637-91-8) → Aurantio-obtusin (67979-25-3)

Guidance literature:

Multi-step reaction with 3 steps

2: DDQ / CH₂Cl₂

3: NaOH

With sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

DOI:10.1016/S0040-4039(00)85117-5

Reference yield:

(4aS,5S,8aR)-5,6-Dimethoxy-5,7-bis-trimethylsilanyloxy-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone → Aurantio-obtusin (67979-25-3)

Guidance literature:

Multi-step reaction with 5 steps

1: HCl / methanol

2: pyridine

4: DDQ / CH₂Cl₂

5: NaOH

With hydrogenchloride; sodium hydroxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)85117-5

upstream raw materials:

Acetic acid 4-hydroxy-3-methoxy-5,8-dioxo-5,8-dihydro-naphthalen-2-yl ester

Acetic acid (5S,8aR,10aS)-4-hydroxy-3,5-dimethoxy-7-methyl-9,10-dioxo-5,6-bis-trimethylsilanyloxy-5,8,8a,9,10,10a-hexahydro-anthracen-2-yl ester

p-benzoquinone