VULPINIC ACID

Base Information

• Chemical Name: VULPINIC ACID
• CAS No.: 521-52-8
• Molecular Formula: C19H14 O5
• Molecular Weight: 322.317
• Mol file: 521-52-8.mol

Synonyms:Benzeneaceticacid, a-(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-,methyl ester, (E)-; Vulpinic acid (6CI); D2(5H),a-Furanacetic acid, 3-hydroxy-5-oxo-a,4-diphenyl-, methyl ester (8CI); NSC 5897

Chemical Property of VULPINIC ACID

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 146-148°C
• Boiling Point: 568.8°Cat760mmHg
• Flash Point: 210.2°C
• PSA: 72.83000
• Density: 1.375g/cm³
• LogP: 3.09680
• Storage Temp.: -20°C Freezer
• Solubility.: Acetonitrile (Slightly, Heated), Chloroform (Slightly), DMSO (Slightly), Methano

Purity/Quality:

99% ^*data from raw suppliers

VulpinicAcid ^*data from reagent suppliers

Safty Information:

• Statements: 28
• Safety Statements: 1-22-45

MSDS Files:

SDS file from LookChem

Useful:

• Description: Vulpinic acid is a lichen metabolite that has been found in L. vulpina and has diverse biological activities. It is active against C. perfringens, B. vulgatus, B. fragilis, B. loescheii, P. acnes, E. faecium, and methicillin-susceptible and -resistant S. aureus (MICs = 4-16 μg/ml). Vulpinic acid (25-800 μM) prevents UVB-induced apoptosis, cytotoxicity, and cytoskeletal modifications in HaCaT human keratinocytes. It also increases scratch wound healing of HaCaT cells. Vulpinic acid (15 μM) reduces hydrogen peroxide-induced production of reactive oxygen species (ROS) and cytotoxicity in human umbilical vein endothelial cells (HUVECs).
• Uses: antiinflammatory, antibacterial, plant growth inhibitor A lichen metabolite with anti-inflammatory properties. A lichen metabolite with anti-inflammatory properties

Technology Process of VULPINIC ACID

There total 21 articles about VULPINIC ACID 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: 95.0%

methanol (67-56-1) + Pulvinic acid lacton (6273-79-6) → vulpic acid (521-52-8,73622-57-8)

Guidance literature:

With sodium hydroxide; for 0.0833333h;

Reference yield: 91.0%

(E)-methyl 2-(4-diazo-3,5-dioxodihydrofuran-2(3H)-ylidene)-2-phenylacetate → vulpic acid (521-52-8,73622-57-8)

Guidance literature:

With dirhodium tetraacetate; In benzene; for 24h;

DOI:10.1021/acs.orglett.6b03087

Reference yield: 71.0%

oxalyl dichloride (79-37-8) + (1-methoxy-2-phenylvinyloxy)trimethylsilane (40195-27-5) → vulpic acid (521-52-8,73622-57-8)

Guidance literature:

oxalyl dichloride; (1-methoxy-2-phenylvinyloxy)trimethylsilane; In dichloromethane; at -78 ℃; for 5h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo048403v

upstream raw materials:

methanol

Pulvinic acid lacton

(E)-5'-(α-methoxycarbonylbenzylidene)cyclohexanespiro-2'-(1',3'-dioxolan)-4'-one

benzeneacetic acid methyl ester

Downstream raw materials:

(E)-5-(α-carboxybenzylidene)-4-hydroxy-3-phenylfuran-2(5H)-one

(E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one

2,5-Dibrom-3,4-dioxo-2,5-diphenyl-adipinsaeure-dimethylester

Refernces

• 1、 Dias, Daniel A.,Urban, Sylvia. "Chemical constituents of the lichen, Candelaria concolor: A complete NMR and chemical degradative investigation". scheme or table. p. 925 - 939. Retrieved 2010/08/19.
• 2、 Willis, Catherine,Bodio, Ewen,Bourdreux, Yann,Billaud, Célia,Gall, Thierry Le,Mioskowski, Charles. "Flexible synthesis of vulpinic acids from tetronic acid". . p. 6421 - 6424. Retrieved 2008/02/12.