55104-32-0

Usage

Uses

Used in Cosmetic Industry:
6-Hydroxyphthalide is used as a fragrance and flavor ingredient for its sweet, fruity scent and taste, enhancing the sensory experience of cosmetic products.
Used in Food Industry:
In the food industry, 6-Hydroxyphthalide serves as a flavoring agent, adding a pleasant aroma and taste to various food products, thereby improving their overall appeal to consumers.
Used in Pharmaceutical Industry:
6-Hydroxyphthalide is used as a potential active pharmaceutical ingredient due to its antimicrobial and antioxidant properties, which can contribute to the development of new treatments and therapies.
Used in Polymer Industry:
Due to its unique chemical structure, 6-Hydroxyphthalide is utilized in the development of polymers, where it can influence the properties of the final product, such as stability, durability, and resistance to environmental factors.
Overall, 6-Hydroxyphthalide is a multifaceted compound with applications spanning across cosmetics, food, pharmaceuticals, and polymers, making it a valuable asset in these industries.

Upstream product

• 57319-65-0 6-aminophthalide 
• 586-38-9 3-Methoxybenzoic acid 
• 19477-73-7 6-bromophthalide 
• 610-93-5 6-nitrophthalide 
• 4741-63-3 6-methoxyphthalide 

Downstream Products

• 1424363-28-9 6-((4-chlorobenzyl)oxy)isobenzofuran-1(3H)-one 
• 1424363-29-0 C₁₅H₁₁BrO₃ 
• 1424363-30-3 6-((4-fluorobenzyl)oxy)isobenzofuran-1(3H)-one 
• 1424363-31-4 6-((4-(trifluoromethyl)benzyl)oxy)isobenzofuran-1(3H)-one 
• 1424363-32-5 C₁₅H₁₁IO₃ 
• 1424363-33-6 C₁₆H₁₄O₃ 
• 1424363-34-7 C₁₅H₁₁BrO₃ 
• 1424363-35-8 C₁₆H₁₄O₃ 
• 1424363-36-9 C₁₆H₁₃ClO₃ 
• 1424363-37-0 C₁₆H₁₃FO₃ 
• 1424363-38-1 C₁₇H₁₆O₃ 
• 1424363-39-2 C₁₇H₁₆O₃ 
• 1424363-40-5 C₁₆H₁₄O₄ 
• 1424363-41-6 C₁₆H₁₃ClO₄ 

Relevant academic research and scientific papers

6-Benzyloxyphthalides as selective and reversible monoamine oxidase B inhibitors with antioxidant and anti-neuroinflammatory activities for Parkinson's disease treatment

A series of 6-benzyloxyphthalides were designed and synthesized as potent monoamine oxidase B inhibitors with antioxidant and anti-neuroinflammatory activities. The representative compounds 8f and 14a exhibited excellent selective MAO-B inhibition activity (IC50 = 1.33 nM, SI = 865; IC50 = 0.02 nM, SI = 40250, respectively) and moderate antioxidant activity (0.34 and 0.36 Trolox equivalent, respectively). Further studies showed that they were competitive and quasi-reversible MAO-B inhibitors. In cellular experiments, they could significantly decrease the production of NO and TNF-α in LPS-stimulated BV-2 cells to perform their in vitro anti-neuroinflammatory activities. Moreover, BBB permeability study and the predicted physicochemical properties indicated they were suitable for the CNS. Finally, in in vivo acute and subacute MPTP-induced mice model of PD, 8f and 14a could significantly improve most behavioral disorders, restore the DA content and decrease the MDA content in the mice striatum, exhibiting better anti-PD effects than clinically used safinamide. Hence, compounds 8f and 14a are identified in our studies as prospective prototype in the research of innovative multifunctional drugs for Parkinson's disease treatment.

Synthesis of cinnamic acid derivatives and leishmanicidal activity against Leishmania braziliensis

Leishmania braziliensis is one of the pathogenic agents of cutaneous and mucocutanoeous leishmaniasis. There are no validated vaccines to prevent the infection and the treatment relies on drugs that often present severe side effects, which justify the efforts to find new potential antileishmanial drugs. An alternative to promote the discovery of new drugs would be the association of different chemical groups of bioactive compounds. Here we describe the synthesis and bioactivity evaluation against L. braziliensis of cinnamic acid derivatives possessing isobenzofuranone and 1,2,3-triazole functionalities. We tested 25 compounds at 10 μM concentration against extracellular promastigotes and intracellular amastigotes during macrophage infection. Most compounds were more active against amastigotes than to promastigotes. The derivatives (E)-3-oxo-1,3-dihydroisobenzofuran-5-yl-(3,4,5-trimethoxy) cinnamate (5c), (1-(3,4-difluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl cinnamate (9g), and (1-(2-bromobenzyl)-1H-1,2,3-triazol-4-yl)methyl cinnamate (9l) were the most effective presenting over 80% toxicity on L. braziliensis amastigotes. While compound 5c is a cinnamate with an isobenzofuranone portion, 9g and 9l are triazolic cinnamic acid derivatives. The action of these compounds was comparable to amphotericin B used as positive control. Ultrastructural analysis revealed that 5c-treated parasites showed impaired cytokinesis and apoptosis triggering. Taken together, these results highlight the potential of cinnamic acid derivatives in development of novel anti-leishmanial drugs.

Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water

A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.

Neuroprotective effects of benzyloxy substituted small molecule monoamine oxidase B inhibitors in Parkinson's disease

The benzyloxy substituted small molecules are well-known highly potent monoamine oxidase B inhibitors, but their therapeutic potential against Parkinson's disease have not been investigated in detail. In this paper, a series of representative benzyloxy substituted derivatives were synthesized and evaluated for MAO-A/B inhibition. In addition, their neuroprotective effects were investigated in 6-OHDA- and rotenone-treated PC12 cells. It was observed that most of the compounds exhibited a marked increase in survival of PC12 cells which treated with the neurotoxins. Among them, 13 exhibited remarkable and balanced neuroprotective potency. The protective effects of 13 against neurotoxins-induced apoptosis were confirmed with flow cytometry and staining methods. Furthermore, 13 also showed good BBB permeability and low toxicity according to in vitro BBB prediction and in vivo acute toxicity test. The results indicated that 13 is an effective and promising candidate to be further developed as disease-modifying drug for Parkinson's disease therapy.

Synthesis, characterization and phytotoxic activity of hydroxylated isobenzofuran-1(3H)-ones

Two hydroxylated isobenzofuranones 3 and 4 were synthesized from benzoic acids. The compounds were fully characterized by IR, NMR (1H and 13C), HRMS, and X-ray crystallography. Compounds 3 and 4 crystallized in the space group Pc and

Inhibition of monoamine oxidase by phthalide analogues

Based on recent reports that the small molecules, isatin and phthalimide, are suitable scaffolds for the design of high potency monoamine oxidase (MAO) inhibitors, the present study examines the MAO inhibitory properties of a series of phthalide [2-benzofuran-1(3H)-one] analogues. Phthalide is structurally related to isatin and phthalimide and it is demonstrated here that substitution at C6 of the phthalide moiety yields compounds endowed with high binding affinities to both human MAO isoforms. Among the nineteen homologues evaluated, the lowest IC50 values recorded for the inhibition of MAO-A and -B were 0.096 and 0.0014 μM, respectively. In most instances, C6-substituted phthalides exhibit MAO-B specific inhibition. Among a series of 6-benzyloxyphthalides bearing substituents on the para position of the phenyl ring the general order of potency was CF3 > I > Br > Cl > F > CH3 > H. The results also show that the binding modes of representative phthalides are reversible and competitive at both MAO isoforms. Based on these data, C6-substituted phthalides may serve as leads for the development of therapies for neurodegenerative disorders such as Parkinson's disease.

Phthalazine derivatives phosphodiesterase 4 inhibitors

The present invention provides a compound selected from the group including: 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-phenyl-phthalazine; 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-1H-phthalazin-2-carboxylic acid methyl ester; benzyl-{3-{1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl}-prop-2-ynyl}-methyl-amine; 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-5-(5-morpholin-4-yl-pent-1-ynyl)-phthalazine dihydrochloride; 3-{1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl}-prop-2-yn-1-ol; 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-morpholin-4-yl-phthalazine; 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-(1,2,4)triazol-1-yl-phthalazine; N→O derivatives thereof; and pharmaceutically acceptable salts thereof. The invention also provides a pharmaceutical composition which includes a therapeutically effective amount of the above compound in admixture with a suitable carrier.