521-52-8

Basic information

• Product Name: VULPINIC ACID
• Synonyms: 3,4-DIHYDROXY-2,5-DIPHENYL-2,4-HEXA-DIENEDIOIC ACID METHYL ESTER 3,6-LACTONE;VULPIC ACID;VULPINIC ACID;(3-hydroxy-5-oxo-4-phenyl-2(5h)-furylidene)phenyl-aceticacimethylester;2,4-hexadienedioicacid,3,4-dihydroxy-2,5-diphenyl-,mono-gamma-lactone,met;alpha)-furanaceticacid,3-hydroxy-5-oxo-alpha,4-diphenyl-delta(sup2(5hmet;PULVINIC ACID METHYL ESTER;methyl 2-(3,5-dioxo-4-phenyl-2-furylidene)-2-phenylacetate
• CAS NO: 521-52-8
• Molecular Formula: C₁₉H₁₄O₅
• Molecular Weight: 322.31
• EINECS: 208-314-1
• Product Categories: Various Metabolites and Impurities;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 521-52-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 146-148°C
• Boiling Point: 568.8°Cat760mmHg
• Flash Point: 210.2°C
• Appearance: /
• Density: 1.375g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: -20°C Freezer
• Solubility: Acetonitrile (Slightly, Heated), Chloroform (Slightly), DMSO (Slightly), Methano
• CAS DataBase Reference: VULPINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: VULPINIC ACID(521-52-8)
• EPA Substance Registry System: VULPINIC ACID(521-52-8)

Safety Data

• Statements: 28
• Safety Statements: 1-22-45
• RIDADR: 3172
• Hazardous Substances Data: 521-52-8(Hazardous Substances Data)

Usage

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).

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 521-52-8 differently. You can refer to the following data:
1. antiinflammatory, antibacterial, plant growth inhibitor
2. A lichen metabolite with anti-inflammatory properties.
3. A lichen metabolite with anti-inflammatory properties

InChI:InChI=1/C19H14O5/c1-23-18(21)15(13-10-6-3-7-11-13)17-16(20)14(19(22)24-17)12-8-4-2-5-9-12/h2-11,20H,1H3/b17-15+

Upstream product

• 67-56-1 methanol 
• 6273-79-6 Pulvinic acid lacton 
• 93796-37-3 (E)-5'-(α-methoxycarbonylbenzylidene)cyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 101-41-7 benzeneacetic acid methyl ester 
• 22628-22-4 (E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one 
• 79-37-8 oxalyl dichloride 
• 40195-27-5 (1-methoxy-2-phenylvinyloxy)trimethylsilane 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 57740-69-9 6-benzylidene-3-hydroxy-4-phenyl-pyran-2,5-dione 
• 6838-54-6 3-hydroxy-1,4-diphenyl-2-butanone 
• 548-59-4 2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinone 
• 122-78-1 phenylacetaldehyde 
• 93554-96-2 α-<(trimethylsilyl)oxy>benzenepropanenitrile 
• 131146-41-3 3-hydroxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 

Downstream Products

• 94579-44-9 2,5-Dibrom-3,4-dioxo-2,5-diphenyl-adipinsaeure-dimethylester 
• 22628-22-4 (E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one 
• 26548-70-9 (E)-5-(α-carboxybenzylidene)-4-hydroxy-3-phenylfuran-2(5H)-one 

Relevant articles and documents

Catalytic Undirected Intermolecular C-H Functionalization of Arenes with 3-Diazofuran-2,4-dione: Synthesis of 3-Aryl Tetronic Acids, Vulpinic Acid, Pinastric Acid, and Methyl Isoxerocomate

A variety of 3-aryl tetronic acids have been synthesized by an undirected, intermolecular C-H functionalization of arenes with 3-diazofuran-2,4-dione. This methodology featured as a key step in the synthesis of a series of naturally occurring 3-aryl-5-arylidene tetronic acids (pulvinates) from commercially available tetronic acid. Salient features of the pulvinic acid synthesis include a one-step, stereoselective synthesis of the C5 arylidene group and a single step introduction of the C3 aryl substituent.

Synthesis of vulpinic and pulvinic acids from tetronic acid

A common precursor, tetronic acid, was used in the synthesis of several vulpinic acids and pulvinic acids, which are pigments found in several lichens and mushrooms. The key features of this method are a two-step alkylidenation of benzyl tetronate and a Suzuki-Miyaura cross-coupling. The synthesis of several natural products, vulpinic acid, pinastric acid, xerocomic acid is described.

Uncatalyzed reaction of silyl ketene acetals with oxalyl chloride: A straightforward preparation of symmetrical pulvinic acids

(Chemical Equation Presented) Several natural pulvinic acids were synthesized. Silyl ketene acetals derived from methyl arylacetates (4 equiv) reacted with oxalyl chloride at -78°C, without the need of adding a catalyst. After treatment of the crude diketones with DBU and acidification with hydrochloric acid, symmetrical pulvinic acids methyl esters were obtained. Saponification of the methyl esters afforded the corresponding pulvinic acids in 60-70% overall yields from oxalyl chloride.