495-32-9

Usage

Uses

Used in Marine Applications:
NODAKENETIN is used as an antifouling agent for preventing the growth of marine organisms on submerged surfaces, such as ship hulls and underwater equipment. Its antifouling properties help reduce drag, improve fuel efficiency, and minimize the environmental impact of biofouling.
Used in Pharmaceutical Applications:
NODAKENETIN is used as a precursor in the synthesis of psoralen and linear furanocoumarins, which have potential applications in the development of new drugs and therapies. Its role in biosynthesis makes it a valuable compound for research and pharmaceutical development.
Used in Chemical Synthesis:
NODAKENETIN is used as a starting material for the synthesis of various chemical compounds, including psoralen and linear furanocoumarins. Its unique structure and properties make it a useful building block for creating new molecules with potential applications in various industries.

Upstream product

• 495-30-7 (S)-marmesinin 
• 13209-79-5 (-)-prantschimgin 
• 1269598-90-4 C₃₀H₃₂O₃Si 
• 1269599-02-1 C₂₀H₂₈O₃Si 
• 1269599-03-2 C₃₀H₃₂O₄Si 
• 21422-04-8 7-demethylsuberosin 
• 1384983-00-9 marmesin-11-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside 
• 495-30-7 1'-O-β-D-glucopyranosyl-(2R)-marmesin 
• 5980-10-9 prangeferol angelate 
• 131623-14-8 6'-O-trans-feruloylnodakenin 
• 35178-20-2 prantschimgin 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 31005-04-6 7-(benzyloxy)-2H-chromen-2-one 
• 374768-02-2 7-[(4-methoxybenzyl)oxy]-2H-chromen-2-one 

Downstream Products

• 64-19-7 acetic acid 
• 108-46-3 recorcinol 
• 53106-45-9 secorin 
• 66-97-7 psoralen 

Relevant academic research and scientific papers

Isolation, structure elucidation, tyrosinase inhibitory, and antioxidant evaluation of the constituents from Angelica dahurica roots

Two undescribed phenolic compounds, angelicols A (1) and B (2) and one undescribed coumarin rhamnoside, angelicoside A (3), together with 17 known compounds (4–20) were isolated from the roots of Angelica dahurica. Their structures were characterized by physical data analyses such as NMR, HRESIMS, and X-ray diffraction. Compounds 2, 3, 5, 6 and L-ascorbic acid (positive control) exhibited obvious DPPH radical scavenging activities with IC50 values of 0.36?mM, 0.43?mM, 0.39?mM, 0.44?mM, 0.25?mM, respectively. At a concentration of 25?μM, all compounds showed weaker tyrosinase inhibition activities (%inhibition 50 = 44.29 ± 0.06?μM).

A simple and efficient approach for the preparation of dihydroxanthyletin, xanthyletin, decursinol and marmesin

A simple and efficient approach has been developed for the preparation of coumarin natural products such as dihydroxanthyletin, xanthyletin, decursinol and marmesin starting from commercially available 2,4-dihydroxybenzaldehyde with very good yields. Wittig homologation and Claisen rearrangement are the protocols used to achieve these molecules.

Synthesis of coumarin derivatives and their cytoprotective effects on t-BHP-induced oxidative damage in HepG2 cells

Coumarins are ubiquitous in higher plants and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of coumarin derivatives on tert-butyl hydroperoxide (t-BHP)-induced oxidative damage in human hepatoma HepG2 cells. A series of coumarin derivatives were prepared and assessed for their cytoprotective effects. Among these, a caffeoyl acid-conjugated dihydropyranocoumarin derivative, caffeoyllomatin, efficiently protected against cell damage elicited by t-BHP. Our findings suggest that caffeoyllomatin appears to be a potent cytoprotective agent.

Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor

The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of β-secretase (BACE1) activity. Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen (31), which has an IC50 value of 9.9 μM. Other furanocoumarin derivatives, for example, 8-geranyloxy-5- methoxypsoralen (35), 8-geranyloxypsoralen (24), and bergamottin (18) inhibited BACE1 activity, with the IC50 values 25.0 μM. Analyses of the inhibition mechanism by Dixon plots and Cornish-Bowden plots showed that compounds 18, 31 and 35 were mixed-type inhibitor. The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.

Asymmetric synthesis of 2-Substituted dihydrobenzofurans and 3-hydroxydihydrobenzopyrans through the enantioselective epoxidation of O-silyl-protected ortho-allylphenols

The Shi-type epoxidation of O-tert-butyldiphenylsilyl (TBDPS) protected o-allylphenols serves as an efficient strategy to construct the dihydrobenzofurans and dihydrobenzopyrans in up to 97% ee. This methodology led to the enantioselective synthesis of (+)-marmesin, (-)-(3′R)-decursinol, and (+)-lomatin.

Glycosides from the methanol extract of Notopterygium incisum

Five new (15) and twelve known (617) different types of glycosides together with a known sesquiterpene triol (18) were isolated from the methanol extract of the rhizomes of Notopterygium incisum. The new structures were elucidated by means of spectroscopic and chemical methods to be pregn-5-en-3,20(S)-diol-3-O- bis - D-glucopyranosyl-(l2,16) - D-glucopyranoside (1), oleuropeic aldehyde 8-O - D-glucopyranoside (2), 2(R)-(3,4-dimethoxyphenyl)-propane-1,3-diol-1-O - D-glucopyranoside (3), eudesman-3,4,11-triol-11-O - D-glucopyranoside (4), and marmesin-11-O - D-glucopyranosyl-(16) - D-glucopyranoside (5). The absolute configuration of the aglycone in compound 3 was assigned by application of Klyne's rule. Georg Thieme Verlag KG Stuttgart - New York.

Four novel furanocoumarin glucosides, candinosides A, B, C and D, from Heracleum candicans Wall

Four novel furanocoumarin glucosides, candinosides A, B, C and D (1-4), were isolated from the roots of Heracleum candicans Wall. Their structures were established using chemical and spectral methods.

Pharmaceutical Composition Useful as Acetylcholinesterase Inhibitors

A pharmaceutical composition useful as acetylcholinesterase inhibitors. The present invention relates to pharmaceutical composition comprising the naturally occurring compounds selected from (±) Marmesin, Columbianetin, Dihydroxanthyletin and substituted coumarin derivatives of 7-allyloxy coumarin, 7-benzyloxy coumarin, 7-methoxy coumarin, 7-acetyloxy coumarin, 4-methyl-7-hydroxy coumarin and 4-methyl-7-acetyloxy coumarin. The said compositions posses a high degree of acetylcholinesterase inhibitory (AChE) property.

Enantioselective total syntheses of (+)-decursin and related natural compounds using catalytic asymmetric epoxidation of an enone

The enantioselective total syntheses of (+)-decursin (1) and related natural dihydropyranocoumarins (-)-prantschimgin (3), (+)-decursinol (4), and (+)-marmesin (5) were achieved for the first time using catalytic asymmetric epoxidation of an enone as the key step. Catalytic asymmetric epoxidation of the enone was effectively promoted by the novel multifunctional asymmetric catalyst generated from La(O-i-Pr)3, BINOL, and Ph3As=O in a 1:1:1 ratio to afford epoxide in 94% yield and 96% ee, which was recrystallized to give optically pure epoxide. After conversion to the common key intermediate (-)-peucedanol (7), all natural dihydropyranocoumarins were synthesized through palladium-catalyzed intramolecular C-O coupling reactions. A possible reaction mechanism of the catalytic asymmetric epoxidation of enones is also described based on X-ray analysis, laser desorption/ionization time-of-flight mass spectrometry, kinetic studies, and asymmetric amplification studies.