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
• Article Data: 17

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

Definition

ChEBI: An organic heterotricyclic compound that is 7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-one substituted by a beta-hydroxy group at position 7 and two methyl groups at position 8. It is isolat d from the roots of Angelica gigas and has been found to possess significant inhibitory activity against acetylcholinesterase enzyme (EC 3.1.1.7).

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

• 623-47-2 propynoic acid ethyl ester 
• 25245-91-4 decursin 
• 325138-04-3 7-(methoxymethoxy)-6-[(Z)-3-oxo-1-butenyl]chromen-2-one 
• 325137-92-6 7-(methoxymethoxy)-6-[(E)-3-oxo-1-butenyl]chromen-2-one 
• 325137-90-4 6-[(1R,2S)-1,2-epoxy-3-oxobutyl]-7-(methoxymethoxy)chromen-2-one 
• 325137-94-8 7-(methoxymethoxy)-6-(trifluoromethanesulfonyl)chromen-2-one 
• 325137-96-0 6-[(1R,2S)-1,2-epoxy-3-hydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 
• 616241-73-7 6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(methoxymethoxy)chromen-2-one 
• 325137-98-2 6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(trifluoromethanesulfonyl)chromen-2-one 
• 325138-00-9 6-[(2S)-3-hydroxy-3-methyl-2-(triethylsilyloxy)butyl]-7-(trifluoromethanesulfonyl)chromen-2-one 
• 21422-04-8 7-demethylsuberosin 
• 1356928-62-5 7-p-methoxybenzyloxy-6-prenylcoumarin 
• 1356928-61-4 4-p-methoxybenzyloxy-o-prenyloxycinnamic acid methyl ester 
• 1356928-60-3 4-p-methoxybenzyloxy-o-hydroxycinnamic acid methyl ester 

Downstream Products

• 130848-06-5 decursinol angelate 
• 25245-91-4 decursin 
• 130848-06-5 (7S)-(+)-trans-2-methyl-but-2-enoic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 
• 1262418-84-7 (7S)-(+)-3-(2-methoxyphenyl)propionic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 
• 1001129-71-0 (7S)-(+)-3-(3,4-dimethoxyphenyl)acrylic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 
• 1001129-76-5 (7S)-(+)-3-(3-methoxyphenyl)acrylic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 
• 1001129-69-6 (7S)-(+)-3-(4-methoxyphenyl)acrylic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 
• 1001129-72-1 (7S)-(+)-3-(3,4,5-trimethoxyphenyl)acrylic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 
• 1262418-82-5 (7S)-(+)-3-phenylpropionic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester 
• 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 
• 1001129-56-1 (7S)-(+)-3-phenylacrylic 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.

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