Auraptene

Base Information

• Chemical Name: Auraptene
• CAS No.: 495-02-3
• Molecular Formula: C19H22 O3
• Molecular Weight: 298.382
• Hs Code.: 2932990090
• NSC Number: 711511
• UNII: F79I1ZEL2E
• DSSTox Substance ID: DTXSID80897576
• Nikkaji Number: J494.165I,J108.361I
• Wikipedia: Auraptene
• Wikidata: Q3629783
• Metabolomics Workbench ID: 46339
• ChEMBL ID: CHEMBL307341
• Mol file: 495-02-3.mol

Synonyms:7-(geranyloxy)coumarin;7-geranyloxycoumarin;aurapten;auraptene

Chemical Property of Auraptene

Chemical Property:

• Vapor Pressure: 1.74E-08mmHg at 25°C
• Melting Point: 91 °C
• Boiling Point: 455.5 °C at 760 mmHg
• Flash Point: 195.4 °C
• PSA: 39.44000
• Density: 1.079 g/cm³
• LogP: 4.86450
• Storage Temp.: ?20°C
• Solubility.: DMSO: >20mg/mL
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 298.15689456
• Heavy Atom Count: 22
• Complexity: 469

Purity/Quality:

98% ^*data from raw suppliers

Auraptene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCCC(=CCOC1=CC2=C(C=C1)C=CC(=O)O2)C)C
• Isomeric SMILES: CC(=CCC/C(=C/COC1=CC2=C(C=C1)C=CC(=O)O2)/C)C
• Description: Auraptene (495-02-3) is a bioactive terpenoid occurring in a variety of citrus fruits and possessing therapeutic potential.1?? Displays neuritogenic activity2?and neuroprotective effects via suppression of inflammation and induction of GDNF and BDNF in neuronal cells3. Attenuates ROS production and enhances mitochondrial respiration which mitigates Parkinson’s disease-like behavior.4?Displays hepatoprotective5?and chemopreventive activity6.
• Uses: Auraptene is a natural bioactive monoterpene coumarin ether. Auraptene has shown a remarkable effect in the prevention of degenerative diseases.

Technology Process of Auraptene

There total 2 articles about Auraptene 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:

7-hydroxy-2H-chromen-2-one (93-35-6) + 1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → auraptene (495-02-3)

Guidance literature:

With potassium carbonate; In acetone; for 3h; Heating;

DOI:10.1016/j.phytochem.2004.08.044

Reference yield:

(R)-6-O-(4-geranyloxy-2-hydroxy)cinnamoylmarmin (142628-36-2) → auraptene (495-02-3) + (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine (5980-09-6,14957-38-1,31946-96-0,32064-13-4,61347-54-4,130548-21-9)

Guidance literature:

In dichloromethane; at 0 ℃; for 7h; Irradiation;

DOI:10.1016/0031-9422(92)80291-L

Reference yield: 79.0%

auraptene (495-02-3) + sodium methylate (124-41-4) → (E)-3-[4-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-2-hydroxy-phenyl]-acrylic acid methyl ester (160238-94-8)

Guidance literature:

In methanol; for 0.5h; Heating;

DOI:10.1271/bbb.60.506

upstream raw materials:

(R)-6-O-(4-geranyloxy-2-hydroxy)cinnamoylmarmin

7-hydroxy-2H-chromen-2-one

1-chloro-3,7-dimethylocta-2,6-diene

Downstream raw materials:

(6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine

(S)-7-(6,7-dihydroxy-3,7-dimethyloct-2E-enyloxy)chromen-2-one

7-(7-hydroxy-3,7-dimethyl-6-oxooct-2E-enyloxy)chromen-2-one

7-(6,7-dihydroxy-3,7-dimethyloct-2E-enyloxy)chromen-2-one

Refernces

• 1、 Masuda, Toshiya,Muroya, Yukari,Nakatani, Nobuji. "7-HYDROXYCOUMARIN DERIVATIVES FROM THE JUICE OIL OF CITRUS HASSAKU". . p. 1363 - 1366. Retrieved 2007/10/02.