27270-89-9

Basic information

• Product Name: (-)-Phyllostine
• Synonyms: (-)-Phyllostine;(1R,6S)-3-Hydroxymethyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione;(1α,6α)-3-(Hydroxymethyl)-7-oxabicyclo[4.1.0]hepta-3-ene-2,5-dione;(5S,6R)-2-(Hydroxymethyl)-5,6-epoxy-2-cyclohexene-1,4-dione;Phyllostine
• CAS NO: 27270-89-9
• Molecular Formula: C7H6O4
• Molecular Weight: 154.1201
• Mol File: 27270-89-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 56 °C
• Boiling Point: 398.9°Cat760mmHg
• Flash Point: 177.4°C
• Appearance: /
• Density: 1.555g/cm³
• Vapor Pressure: 5.07E-08mmHg at 25°C
• Refractive Index: 1.589
• PKA: 13.40±0.10(Predicted)
• CAS DataBase Reference: (-)-Phyllostine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Phyllostine(27270-89-9)
• EPA Substance Registry System: (-)-Phyllostine(27270-89-9)

Safety Data

• Hazardous Substances Data: 27270-89-9(Hazardous Substances Data)

Usage

General Description

(-)-Phyllostine is a naturally occurring alkaloid primarily found in the leaves of Phyllostachys nigra, a species of bamboo. It possesses a unique chemical structure consisting of a quinolizidine core, and has been found to exhibit a variety of pharmacological activities. Research has shown that (-)-Phyllostine possesses anti-inflammatory, anti-tumor, and antifungal properties. It has also demonstrated potential as a therapeutic agent in the treatment of cancer and other diseases. Furthermore, it has attracted considerable interest from the scientific community due to its intricate chemical structure and potential medicinal applications. Overall, (-)-Phyllostine represents an intriguing natural compound with diverse biological activities that warrant further exploration and research.

InChI:InChI=1/C7H6O4/c8-2-3-1-4(9)6-7(11-6)5(3)10/h1,6-8H,2H2/t6-,7+/m1/s1

Upstream product

• 649572-55-4 (7R,8S,9S)-9-tert-butyldimethylsilyloxy-2,6-dioxo-7,8-epoxy-1,3-dioxa-spiro[4.5]decane 
• 649572-45-2 (2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-hydroxy-6-hydroxymethyl-1-cyclohexanone 
• 394250-86-3 (1R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[4.1.0]heptan-2-one 
• 394250-87-4 (-)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methylene-1-cyclohexanone 
• 792910-38-4 (1R,6S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-2,5-dione 
• 649572-58-7 C₈H₈O₆ 
• 256662-98-3 ent-RKTS-33 
• 67772-76-3 (+)-5-hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one 

Downstream Products

• 256662-98-3 ent-RKTS-33 

Relevant articles and documents

Parasitenone, a new epoxycyclohexenone related to gabosine from the marine-derived fungus Aspergillus parasiticus

Bioassay-guided fractionation of an organic extract of the broth from the marine-derived fungus culture of Aspergillus parasiticus led to the isolation and subsequent structural elucidation of a new gabosine derivative, parasitenone (1), and two known benzyl alcohols, 3-chloro-4,5-dihydroxybenzyl alcohol (2) and gentisyl alcohol (3). The benzyl alcohols (2, 3) were identified as the principal free radical scavenging components. Parasitenone (1) also showed moderate activity in the free radical scavenging assay.

Synthesis of (+)-Epoxydon, (–)-Phyllostine, (–)-RKTS 33, and (–)-Parasitenone Featuring Selective Sulfonylation and Oxirane Ring Closure of Aldol Cyclization Products

Two new synthetic approaches to anhydrogabosines are developed from the polyoxygenated aldol cyclization intermediates, bearing different O-protecting groups, which were transformed to various gabosine-type cyclitols. Selective sulfonylation on the required hydroxyl group of the intermediates and the subsequent oxirane ring closure are employed as the key steps in both approaches, by which (+)-epoxydon, (–)-phyllostine, (–)-RKTS 33, and (–)-parasitenone were synthesized from δ-d-gluconolactone.

Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB

Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-κB (NF-κB) inhibitor that inhibits DNA binding of NF-κB components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-κB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-κB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.

Total synthesis of (+)-epiepoformin and (-)-phyllostine

An efficient asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine has been achieved using the chiral building block available from the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone. Since (-)-theobroxide was derived from the same precursor of (+)-epiepoformin, the formal total synthesis of (-)-theobroxide has also been achieved.