30508-27-1

Basic information

• Product Name: licoricidin
• Synonyms: licoricidin;7-O-Demethyllicorisoflavan A;Licorisoflavan B;1,3-Benzenediol,4-[(3R)-3,4-dihydro-7-hydroxy-5-methoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-3-yl]-2-(3-methyl-2-buten-1-yl)-
• CAS NO: 30508-27-1
• Molecular Formula: C26H32O5
• Molecular Weight: 424.52928
• Mol File: 30508-27-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 161.0-162.5℃
• Boiling Point: 610.8°Cat760mmHg
• Flash Point: 323.2°C
• Appearance: /
• Density: 1.171g/cm³
• Vapor Pressure: 1.63E-15mmHg at 25°C
• Refractive Index: 1.597
• PKA: 10.10±0.40(Predicted)
• CAS DataBase Reference: licoricidin(CAS DataBase Reference)
• NIST Chemistry Reference: licoricidin(30508-27-1)
• EPA Substance Registry System: licoricidin(30508-27-1)

Safety Data

• Hazardous Substances Data: 30508-27-1(Hazardous Substances Data)

Usage

General Description

Licoricidin is a natural compound found in licorice root, and it is known for its various biological activities. It has been recognized for its anti-inflammatory, antiviral, and anticancer properties. Licoricidin has been shown to inhibit the growth of various cancer cell lines, including breast cancer, lung cancer, and leukemia. It also has demonstrated antiviral activity against HIV-1 and influenza virus. Additionally, licoricidin has been found to have anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines. Overall, licoricidin is a promising compound with potential therapeutic applications in cancer, viral infections, and inflammatory diseases.

InChI:InChI=1/C26H32O5/c1-15(2)6-8-19-22(27)11-10-18(25(19)29)17-12-21-24(31-14-17)13-23(28)20(26(21)30-5)9-7-16(3)4/h6-7,10-11,13,17,27-29H,8-9,12,14H2,1-5H3/t17-/m0/s1

Synthetic route

(+)-(R)-licoricidin (30508-27-1) + dimethyl sulfate (77-78-1) → 6-[(R)-5,7-Dimethoxy-6-(3-methyl-but-2-enyl)-chroman-3-yl]-3-methoxy-2-(3-methyl-but-2-enyl)-phenol

Conditions	Yield
With potassium carbonate In acetone

acetic anhydride (108-24-7) + (+)-(R)-licoricidin (30508-27-1) → (+)-(R)-licoricidin triacetate

Conditions	Yield
In pyridine

(+)-(R)-licoricidin (30508-27-1) → 6-((R)-5-Methoxy-8,8-dimethyl-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromen-3-yl)-2,2-dimethyl-chroman-5-ol + 8-((R)-5-Methoxy-8,8-dimethyl-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromen-3-yl)-2,2-dimethyl-chroman-5-ol

Conditions	Yield
With hydrogenchloride In methanol

(+)-(R)-licoricidin (30508-27-1) → 4',7-dihydroxy-5-methoxy-6,3'-diprenylisoflavanquinone (1346768-14-6)

Conditions	Yield
With sodium hydroxide In ethanol for 2h;

(+)-(R)-licoricidin (30508-27-1) → C30H34O7

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 16 h 2: palladium dichloride / ethanol; water / 48 h / 20 °C View Scheme

(+)-(R)-licoricidin (30508-27-1) → 1-methoxyerythrabyssin II (1006718-45-1) + licorisoflavan D (1551035-71-2)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.0833333h; Reflux;	A 1 mg B 9.9 mg

(+)-(R)-licoricidin (30508-27-1) → licorisoflavan C (1551035-46-1) + licorisoflavan D (1551035-71-2) + licorisoflavan E

Conditions	Yield
With palladium dichloride In ethanol at 20℃; for 4h;	A 5.2 mg B 3.2 mg C 7.6 mg

(+)-(R)-licoricidin (30508-27-1) → licorisoflavan E

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 16 h 2: palladium dichloride / ethanol; water / 48 h / 20 °C 3: sodium hydroxide; water / 0.5 h View Scheme

acetic anhydride (108-24-7) + (+)-(R)-licoricidin (30508-27-1) → 7,2'-diacetyllicoricidin (1542237-27-3) + 7,4'-diacetyllicoricidin (1542237-28-4) + 2',4'-diacetyllicoricidin (1542237-29-5)

Conditions	Yield
With pyridine for 16h;	A 24.2 mg B 6.7 mg C 54.6 mg

Downstream Products

• 1542237-27-3 7,2'-diacetyllicoricidin 
• 1542237-28-4 7,4'-diacetyllicoricidin 
• 1542237-29-5 2',4'-diacetyllicoricidin 
• 1551035-46-1 licorisoflavan C 
• 1551035-71-2 licorisoflavan D 
• 1006718-45-1 1-methoxyerythrabyssin II 
• 1346768-14-6 4',7-dihydroxy-5-methoxy-6,3'-diprenylisoflavanquinone