13401-40-6

Basic information

• Product Name: Phaseollin
• Synonyms: (6bR)-6bβ,12bβ-Dihydro-3,3-dimethyl-3H,7H-furo[3,2-c:5,4-f']bis[1]benzopyran-10-ol;(6bR,12bR)-6b,12b-Dihydro-3,3-dimethyl-3H,7H-furo[3,2-c:5,4-f']bis[1]benzopyran-10-ol;Phaseolin【fungicide】;(6bR-cis)-6b,12b-Dihydro-3,3-dimethyl-3H,7H-furo[3,2-c:5,4-f']bis[1]benzopyran-10-ol;Phaseolin;3H,7H-Furo(3,2-C:5,4-F')bis(1)benzopyran-10-ol, 6B,12B-dihydro-3,3-dimethyl-, (6br-cis)-
• CAS NO: 13401-40-6
• Molecular Formula: C₂₀H₁₈O₄
• Molecular Weight: 322.358
• Product Categories: Iso-Flavones
• Mol File: 13401-40-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 177-178°
• Boiling Point: 467.473 °C at 760 mmHg
• Flash Point: 236.519 °C
• Appearance: /
• Density: 1.287 g/cm³
• Vapor Pressure: 2.32E-09mmHg at 25°C
• Refractive Index: 1.628
• PKA: 9.13(at 25℃)
• CAS DataBase Reference: Phaseollin(CAS DataBase Reference)
• NIST Chemistry Reference: Phaseollin(13401-40-6)
• EPA Substance Registry System: Phaseollin(13401-40-6)

Safety Data

• Hazardous Substances Data: 13401-40-6(Hazardous Substances Data)

Usage

Description

Phaseollin is a prenylated pterocarpan and an organic heteropentacyclic compound, specifically a 2,3,6b,12b-tetrahydro-1H,7H-chromeno[6',5':4,5]furo[3,2-c]chromen-10-ol with both hydrogens at position 3 replaced by methyl groups (the R,R stereoisomer). It is naturally found in the seeds of Phaseolus vulgaris (French bean) and in the stems of Erythrina subumbrans.

Uses

Used in Pharmaceutical Industry:
Phaseollin is used as a bioactive compound for its potential medicinal properties. It has been found to possess various pharmacological activities, such as anti-inflammatory, antifungal, and antimicrobial effects, making it a promising candidate for the development of new drugs and therapies.
Used in Agricultural Industry:
Phaseollin is used as a natural pesticide for its insecticidal and antifungal properties. It can be employed to protect crops from pests and diseases, offering an environmentally friendly alternative to synthetic chemical pesticides.
Used in Cosmetic Industry:
Due to its antimicrobial and anti-inflammatory properties, Phaseollin can be used as an ingredient in the cosmetic industry for the development of skincare products, such as creams, lotions, and ointments, that promote skin health and protect against harmful microorganisms.
Used in Food Industry:
Phaseollin's natural antimicrobial properties can be utilized in the food industry to enhance the shelf life of perishable products and reduce the risk of foodborne illnesses caused by harmful bacteria and fungi.

InChI:InChI=1/C20H18O4/c1-20(2)8-7-14-16(24-20)6-5-12-15-10-22-17-9-11(21)3-4-13(17)19(15)23-18(12)14/h3-9,15,19,21H,10H2,1-2H3

Upstream product

• 111492-46-7 3-(2-hydroxy-4-methoxymethoxyphenyl)-1,1-dimethoxy-2-(5-methoxymethoxy-2,2-dimethyl-3-phenylthiochroman-6-yl)-propan-3-one 
• 111492-47-8 3-(5-methoxymethoxy-2,2-dimethyl-3-phenylsulphinylchroman-6-yl)-7-methoxymethoxy-4H-benzopyran-4-one 
• 91078-13-6 3-(5-methoxymethoxy-2,2-dimethyl-3-phenylthiochroman-6-yl)-7-methoxymethoxy-4H-benzopyran-4-one 
• 91078-09-0 1,1-dimethoxy-2-(5-methoxymethoxy-2,2-dimethyl-2H-benzopyran-6-yl)-3-(2-hydroxy-4-methoxymethoxyphenyl)propane-3-one 
• 60008-02-8 glabrone 
• 91078-10-3 3-(5-methoxymethoxy-2,2-dimethyl-2H-benzo-pyran-6-yl)-7-methoxymethoxy-4H-benzopyran-4-one 

Related news

Detoxification of Phaseollin (cas 13401-40-6) by Fusarium solani f. sp. phaseoli08/04/2019

Evidence is presented indicating that the bean pathogen Fusarium solani f. sp. phaseoli is able to metabolize the phytoalexin phaseollin in vitro. Phaseollin is metabolized in shake cultures of actively growing mycelium exposed to a concentration non-inhibitory to growth. An inhibitory concentra...detailed

Phaseollin (cas 13401-40-6) metabolism and tolerance in Fusarium solani f. sp. phaseoli08/03/2019

Metabolism of the bean phytoalexin, phaseollin, to 1a-hydroxyphaseollone by Fusarium solani f. sp. phaseoli appears to occur by way of an inducible mono-oxygenase. Evidence for this conclusion is that: (1) pretreatment with selected aromatic compounds, as well as phaseollin itself, enhanced the ...detailed

Toxic effects of Phaseollin (cas 13401-40-6) on plant cells08/02/2019

Plant cells, from bean and tobacco suspension cultures and from pods and hypocotyls of bean, were rapidly killed following immersion in solutions containing 30 μg phaseollin per ml. These concentrations inhibited the respiration of bean cells within 2 min of treatment and also reduced the growt...detailed

Metabolism of Phaseollin (cas 13401-40-6) by Septoria nodorum and other non-pathogens of Phaseolus vulgaris07/31/2019

Phaseollin is metabolised by cultures of Septoria nodorum, a non-pathogen of bean, into cis and trans isomers of 12,13-dihydrodihydroxyphaseollin. These products are much less fungitoxic than phaseollin which suggests that the capacity to detoxify phytoalexins is not confined to pathogenic fungi.detailed

Phaseollin (cas 13401-40-6) formation and metabolism in Phaseolus vulgaris07/30/2019

Following fungal-inoculation, P. vulgaris was found to produce small amounts of 7,4′-dihydroxyisoflavone (daidzein), 7,2′,4′-trihydroxyisoflavone, 7,2′,4′-trihydroxyisoflavanone, (6aR, 11aR)-3,9-dihydroxypterocarpan, and (3R)-7,2′,4′-trihydroxyisoflavan. The structures of the latter four ...detailed

Pterocarpans Phaseollin (cas 13401-40-6) and neorautenol isolated from Erythrina addisoniae induce apoptotic cell death accompanied by inhibition of ERK phosphorylation07/29/2019

The genus Erythrina (Leguminosae), consisting of over 100 different species, is distributed in tropical regions. In traditional medicine, Erythrina species are used to treat cancer, but little is known about the anticancer mechanisms. From the stem bark of Erythrina addisoniae Hutch. & Dalziel, ...detailed

Metabolism of Phaseollin (cas 13401-40-6) by Colletotrichum lindemuthianum07/28/2019

Two metabolites of the phytoalexin phaseollin (1) produced by cultures of the fungus Colletotrichum lindemuthianum have been assigned structures (3) and (4).detailed

Biosynthesis of the phytoalexin Phaseollin (cas 13401-40-6) in Phaseolus vulgaris07/27/2019

Feeding experiments in CuCl2-treated French bean (Phaseolus vulgaris) seedlings have demonstrated that labelled 2′,4′,4-trihydroxychalcone, daidzein, 7,2′,4′-trihydroxyisoflavone, 3,9-dihydroxypterocarpan and phaseollidin are all good precursors of the pterocarpan phytoalexin phaseollin. The...detailed

Effects of Phaseollin (cas 13401-40-6) on membrane leakage in red beet vacuoles and tonoplast vesicles07/26/2019

Acting in a manner similar to that of glyceollins I and III, phaseollin appears to inhibit proton transport in red beet tonoplast vesicles. In the presence of 80 μM phaseollin, proton transport in tonoplast vesicles was inhibited by >90%. This inhibition appears to be due to increased conductan...detailed

Relevant articles and documents

Synthesis of the Phytoalexin (+/-)-Phaseollin: 3-Phenylthiochromans as Masked 2H-Chromenes and o-Prenyl Phenols

Phenylthiyl radicals are shown to add regiospecifically to 2H-chromenes to afford 3-phenylthiochromans (8), (10), (13), (14), and (15).The sulphide (15), as equivalent to a chromene protected against acid and oxidation, has been used in two syntheses of (+/-)-phaseollin, a major phytoalexin of beans and other legumes, via the sequence (17)->(18)->(19)->(20)->(21)->(+/-)-(1) or (19)->(22)->(23)->(+/-)-(1).Also the 3-phenylthiochromans, on electron transfer from metal naphthalenide or a mercury cathode, open to o-prenylphenols, providing a two step route to biogenetically important phenols from chromenes which is tolerant of free phenol and carbonyl functions and trisubstituted double bonds.