26548-70-9

Usage

Uses

Used in Pharmaceutical Industry:
Scrophularic acid is used as an anti-inflammatory and analgesic agent for the treatment of inflammatory conditions such as rheumatoid arthritis and osteoarthritis. It is believed to exert its therapeutic effects by inhibiting the production of inflammatory mediators, such as prostaglandins.
Used in Antioxidant Applications:
Scrophularic acid has been investigated for its potential antioxidant properties, which could make it a promising candidate for the development of new pharmaceuticals for the treatment of inflammatory diseases. Its antioxidant properties may contribute to the prevention and management of oxidative stress-related conditions.

InChI:InChI=1/C18H12O5/c19-15-13(11-7-3-1-4-8-11)18(22)23-16(15)14(17(20)21)12-9-5-2-6-10-12/h1-10,22H,(H,20,21)/b16-14+

Upstream product

• 6273-79-6 Pulvinic acid lacton 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 6838-54-6 3-hydroxy-1,4-diphenyl-2-butanone 
• 57740-69-9 6-Benzyliden-3-hydroxy-4-phenyl-2H-pyran-2,5(6H)-dion 
• 131146-48-0 3-methoxy-4-phenyl-6-(phenylmethylene)-2H-pyran-2,5(6H)-dione 
• 131146-48-0 6-benzylidene-3-methoxy-4-phenylpyran-2,5-dione 
• 22628-22-4 (E)-4-methoxy-5-(α-methoxycarbonylbenzylidene)-3-phenylfuran-2(5H)-one 
• 137532-11-7 3-oxo-1,4-diphenylbutan-2-yl ethyl oxalate 
• 131146-47-9 6-bromo-3-methoxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 
• 131146-44-6 3-methoxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 
• 131146-41-3 3-hydroxy-4-phenyl-6-(phenylmethyl)-2H-pyran-2,5(6H)-dione 
• 93554-96-2 α-<(trimethylsilyl)oxy>benzenepropanenitrile 
• 122-78-1 phenylacetaldehyde 
• 548-59-4 2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinone 

Relevant academic research and scientific papers

Chemical constituents of the lichen, Candelaria concolor: A complete NMR and chemical degradative investigation

A detailed chemical and spectroscopic investigation of the terrestrial lichen Candelaria concolor has yielded several lichenic metabolites belonging to the pulvinic acid series, as well as several depside derivatives including pulvinic dilactone (1), vulpinic acid (4) and calycin (5). The chemical transformation of 1 to pulvinic acid (3) is reported for the first time, as is the conversion of atranorin (6) to 5-chloroatranorin (7) and then finally to 5,5'-dichloroatranorin (8) under very mild conditions. Also presented is the complete 1D and 2D NMR assignment for compounds 1, 3, 4, 5 and 8, including partial NMR chemical shift assignments for the unstable depside (7). Previously, these metabolites had only been partially assigned by NMR spectroscopy.

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.

Synthesis of Grevillins, Novel Pyrandione Pigments of Fungi. Biogenetic Interrelationships between Grevillins, Pulvinic Acids, Terphenylquinones and Xylerythrins

A synthesis of the grevillin group of pyrandione pigments, e.g. 3, 23 and 24 present in fungi is described.The synthesis, which is based on a biogenetic model, uses bis-benzylacyloins 9 and their corresponding oxalate derivatives as key intermediates (Scheme 3).Treatment of the grevillins 25a-c with sodium ethoxide in ethanol effects their quantitative isomerisation into the corresponding terphenylquinone pigments 4a-c.Perkin-type condensations between the terphenylquinones 4 and arylacetic acids in the presence of sodium acetate-acetic anhydride then produces the xylerythrin pigments 29a-e, whereas rearrangements of 4 in the presence of dimethyl sulphoxide leads to pulvinic acid derivative, e.g. 31, 32 and 5.These synthetic studies interrelate the biosynthetic origins of the pigment types 3, 4, 5 and 8 together with the related pulvinones 6 and furanone 7 fungal pigments.

SYNTHESIS OF GREVILLINS AND THEIR BIOGENETIC INTERRELATIONSHIP WITH TERPHENYLQUINONES, XYLERYTHRINS AND PULVINIC ACIDS

A synthesis of the grevillin group , of pigments present in fungi, using benzylacyloins, viz (9), as key intermediates is described, and the biogenetic interrelationships between them and the terphenylquinone, xylerythrin and pulvinic acid families of natural colouring matter, are exemplified with the in vitro conversions (16)-(17), (17)-(20) and (17)-(22).

Dioxolanones as Synthetic Intermediates. Part 3. Biomimetic Synthesis of Pulvinic Acids

The reaction of the phosphorane (16) with methyl arylglyoxylates gives 5-(α-methoxycarbonylarylidene)-2,2-pentamethylene-1,3-dioxolan-4-ones which have been treated with the lithium enolates of t-butyl phenylacetic esters to provide a biomimetic synthesis of pulvinic acids.By this method pulvinic acid (2), vulpinic acid (1), and the unsymmetrically substituted compounds, leprapinic acid (3), and xerocomic acid (4) have been prepared; the last named was obtained via an intermediate (28) in which the phenolic groups were protected as benzyl ethers.