23458-02-8

Basic information

• Product Name: Decursinol
• Synonyms: Decursinol;(7S)-7α-Hydroxy-8,8-dimethyl-7,8-dihydro-2H,6H-benzo[1,2-b:5,4-b']dipyran-2-one;(S)-7,8-Dihydro-7-hydroxy-8,8-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-2-one;(3S)-3-Hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• CAS NO: 23458-02-8
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.261
• Mol File: 23458-02-8.mol

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: 433.6°Cat760mmHg
• Flash Point: 167.9°C
• Appearance: /
• Density: 1.293g/cm³
• Vapor Pressure: 2.74E-08mmHg at 25°C
• Refractive Index: 1.592
• PKA: 13.87±0.40(Predicted)
• CAS DataBase Reference: Decursinol(CAS DataBase Reference)
• NIST Chemistry Reference: Decursinol(23458-02-8)
• EPA Substance Registry System: Decursinol(23458-02-8)

Safety Data

• Hazardous Substances Data: 23458-02-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Decursinol is used as a bioactive compound for its significant inhibitory activity against the acetylcholinesterase enzyme. This property makes it a potential candidate for the development of drugs targeting neurological disorders and conditions related to the overactivity of acetylcholinesterase.
Used in Natural Product Research:
Decursinol, being a naturally occurring compound isolated from the roots of Angelica gigas, is used as a subject of study in natural product research. Its unique chemical structure and biological activities can provide insights into the development of new drugs and therapeutic agents, as well as contribute to the understanding of the medicinal properties of plants in traditional medicine.
Used in Neurological Disorder Treatment:
Decursinol is used as a potential therapeutic agent for the treatment of neurological disorders associated with the overactivity of acetylcholinesterase enzyme. By inhibiting this enzyme, Decursinol may help in managing the symptoms of conditions such as Alzheimer's disease, myasthenia gravis, and other related disorders.
Used in Cognitive Enhancement:
Due to its inhibitory activity against the acetylcholinesterase enzyme, Decursinol is used as a cognitive enhancer. It may help improve memory, learning, and overall cognitive function by modulating the levels of acetylcholine, a neurotransmitter crucial for these processes.
Used in Agrochemical Industry:
Decursinol, being a naturally occurring compound with significant biological activities, can be used in the agrochemical industry for the development of novel pesticides, herbicides, or other bioactive agents. Its unique chemical structure and properties may provide new insights into the design and synthesis of environmentally friendly and effective agrochemicals.

InChI:InChI=1/C14H14O4/c1-14(2)12(15)6-9-5-8-3-4-13(16)17-10(8)7-11(9)18-14/h3-5,7,12,15H,6H2,1-2H3/t12-/m0/s1

Upstream product

• 1186136-02-6 agasyllin 
• 27421-19-8 7-(2-methylbut-3-en-2-yloxy)-2H-chromen-2-one 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 623-47-2 propynoic acid ethyl ester 
• 21422-04-8 7-demethylsuberosin 
• 541-47-9 3-Methylbutenoic acid 
• 25245-91-4 decursin 
• 108-46-3 recorcinol 
• 354576-62-8 acetic acid 2,2-dimethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalen-5-yl ester 
• 94527-05-6 4,7-dihydroxy-2,2-dimethylchroman 
• 19012-98-7 7-acetoxy-2,2-dimethyl-2H-chromene 
• 19012-97-6 2,2-dimethyl-7-hydroxy-2H-1-benzopyran 
• 17771-33-4 7-hydroxy-2,2-dimethyl-chroman-4-one 
• 21074-63-5 2H,6H benzo <1,2-b, 5,4-b'> dipyran 2-one 

Downstream Products

• 5928-25-6 2,2-dimethyl-8-oxo-2,3,4,8-tetrahydropyrano[3,2-g]chromen-3-yl 3-methylbut-2-enoate 
• 1448845-35-9 decursinol phenylthiocarbamate 
• 1001129-59-4 (7S)-(+)-3-(3,4-dihydroxy-phenyl)-acrylic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 
• 130848-06-5 decursinol angelate 
• 1038809-82-3 8,8-dimethyl-6H-pyrano[3,2-g]chromen-2,7-dione 7-[O-cinnamoyl-oxime] 
• 1400980-59-7 (7S)-(+)-3-(3,4-dimethoxyphenyl)propionic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 

Relevant articles and documents

Pyranocoumarin derivative as well as preparation method and application thereof

The invention belongs to the technical field of medicine, and relates to a pyranocoumarin derivative, a preparation method and uses thereof. The pyranocoumarin derivative has a structural general formula represented by a formula I, wherein R is H, halogen, OH, NH2, COOH, C1-C6 alkyl, C1C6 alkoxy, C1-C6 alkylamino, and 5-10-membered heterocyclic group, and n is 06. The pyranocoumarin derivative isapplied to preparation of a medicine for preventing and treating prostatic cancer. According to the application disclosed by the invention, the inhibition effect of the peucedanum praeruptorum alcoholesterification derivative substituted at the 3' position of the pyranoid ring in the pyranoid coumarin on human prostate cancer cells is proved by evaluating the in-vitro inhibition activity of the peucedanum praeruptorum alcohol esterification derivative substituted at the 3' position of the pyranoid ring in the pyranoid coumarin on human prostate cancer cells; the compound can be used as a potential drug for preventing and treating prostate cancer for deep development, and has important practical value and application prospect in the field of preparation of antitumor drugs.

Discovery of tricyclic pyranochromenone as novel bruton’s tyrosine kinase inhibitors with in vivo antirheumatic activity

Bruton’s tyrosine kinase (BTK) is an attractive target for treating patients with B cell malignancies and autoimmune diseases. Many BTK inhibitors have been identified; however, like other kinase inhibitors, they lack diversity in their core structures. Therefore, it is important to secure a novel scaffold that occupies the adenine-binding site of BTK. We screened an in-house library of natural products and their analogs via a biochemical assay to identify a novel scaffold for targeting BTK. A pyranochromenone scaffold, derived from a natural active component decursin, was found to be effective at targeting BTK and was selected for further optimization. A series of pyranochromenone analogs was synthesized through the modification of pyranochromenone at the C7 position. Pyranochromenone compounds with an electrophilic warhead exhibited promising BTK inhibitory activity, with IC50 values in the range of 0.5–0.9 μM. A docking study of the representative compound 8 provided a reasonable explanation for compound activity. Compound 8 demonstrated good selectivity over other associated kinases and decreased the production of proinflammatory cytokines in THP cells. Moreover, compound 8 presented significant in vivo efficacy in a murine model of collagen-induced arthritis.

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.

Synthesis and in vitro assay of new triazole linked decursinol derivatives showing inhibitory activity against cholinesterase for Alzheimer's disease therapeutics

With the goal of developing Alzheimer's disease therapeutics, we have designed and synthesized new triazole linked decursinol derivatives having potency inhibitory activities against cholinesterase [acetylcholinesterase (AChE) and butyrylcholinesterase (B

A synthetic decursin analog with increased in vivo stability suppresses androgen receptor signaling in vitro and in vivo

Summary: Targeting androgen receptor (AR) signaling with agents distinct from current antagonist drugs remains a rational approach to the prevention and treatment of prostate cancer (PCa). Our previous studies have shown that decursin and isomer decursinol angelate (DA), isolated from the Korean medicinal herb Angelica gigas Nakai, interrupt AR signaling and possess anti-PCa activities in vitro. In the LNCaP PCa cell model, these pyranoccoumarin compounds exhibit properties distinct from currently used antagonists (e.g., Casodex). However, both are rapidly de-esterified to decursinol, a partial AR agonist. We report here that a synthetic decursin analog, decursinol phenylthiocarbamate (DPTC), has greater in vivo stability than the parent compounds. DPTC-decursinol conversion was undetectable in mice. Furthermore, in LNCaP cells, DPTC decreased prostate specific antigen (PSA) expression, down-regulated AR abundance and mRNA and inhibited AR nuclear translocation. The effect of DPTC on AR and PSA mRNA and protein abundance was also observed in VCaP cells expressing wild type AR. DPTC inhibited growth of both PCa cell lines through G1 cell cycle arrest and apoptosis, as did decursin and DA. Furthermore, i.p. administration of DPTC for 3 weeks suppressed the expression of AR target genes probasin and Nkx3.1 in mouse prostate glands. Overall, our data suggest that DPTC represents a prototype lead compound for development of in vivo stable and active novel decursin analogs for the prevention or therapy of PCa.

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.

Decursin and decursinol angelate selectively inhibit NADH-fumarate reductase of Ascaris suum

NADH-fumarate reductase (NFRD) is a key enzyme in many anaerobic helminths. Decursin and decursinol angelate have been isolated from the roots of Angelica gigas Nakai (Apiaceae) as NFRD inhibitors. They inhibited Ascaris suum NFRD with IC50 values of 1.1 and 2.7 μM, respectively. Their target is the electron transport enzyme complex I. Since the inhibitory activities of decursin against bovine heart complexes are weak, it is a selective inhibitor of the nematode complex I. In contrast, decursinol angelate moderately inhibits bovine heart complexes II and III. Decursinol inhibits A. suum NFRD to a similar extent, but its target is complex II. It also inhibits bovine heart complexes II and III. Georg Thieme Verlag KG Stuttgart.

An efficient synthesis of (+)-decursinol from umbelliferone

An efficient, practical and enantioselective total synthesis of (+)-decursinol, which has diverse range of biological properties including anti-cancer, anti-Helicobacter pylori, and strong antinociceptive activities, has been achieved in five steps with 41.4% overall yield from umbelliferone. The improved ring construction from coumarin to linear pyranocoumarin has been obtained through quinonemethide intermediate by using phenylboronic acid with propionic acid.

Microbial metabolism. Part 8. The pyranocoumarin, decursin

Microbial transformation of the cancer chemopreventive agent, decursin (1) with Sepedonium chrysospermem (ATCC 13378) yielded two metabolites, (+)-decursinol (2) and (-)-cis-decursidinol (3). The structures were established by spectroscopic data.