17303-67-2

Basic information

• Product Name: goniothalamin
• Synonyms: goniothalamin;(6R)-6α-[(E)-Styryl]-5,6-dihydro-2H-pyran-2-one;(R)-(+)-Goniothalamin;(R)-Goniothalamin;[R,(+)]-5,6-Dihydro-6α-[(E)-2-phenylethenyl]-2H-pyran-2-one;(6R)-(+)-5,6-Dihydro-6-styryl-2-pyrone;(6R)-(+)-Goniothalamin
• CAS NO: 17303-67-2
• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.236
• Mol File: 17303-67-2.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 386°Cat760mmHg
• Flash Point: 162.2°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 3.67E-06mmHg at 25°C
• Refractive Index: 1.668
• CAS DataBase Reference: goniothalamin(CAS DataBase Reference)
• NIST Chemistry Reference: goniothalamin(17303-67-2)
• EPA Substance Registry System: goniothalamin(17303-67-2)

Safety Data

• Hazardous Substances Data: 17303-67-2(Hazardous Substances Data)

Usage

General Description

Goniothalamin is a natural product isolated from plants and has been widely studied for its potential bioactive properties. It is a cytotoxic compound that has shown promise in fighting against various cancer cell lines, including breast, lung, and prostate cancers. Goniothalamin also exerts anti-inflammatory and anti-microbial effects, making it a potentially valuable compound for medicinal applications. Its mode of action involves inducing apoptosis in cancer cells and disrupting the cell cycle progression, making it an attractive candidate for further research and potential drug development. However, further studies are needed to fully understand its mechanisms of action and potential side effects before it can be utilized for clinical applications.

InChI:InChI=1/C13H12O2/c14-13-8-4-7-12(15-13)10-9-11-5-2-1-3-6-11/h1-6,8-10,12H,7H2/b10-9+/t12-/m1/s1

Upstream product

• 124851-36-1 (E)-2-styryl-3,4-dihydro-2H-pyran 
• 70670-14-3 (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one 
• 639798-55-3 (1R)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 
• 129694-51-5 (2R,6R)-6-((E)-Styryl)-5,6-dihydro-2H-pyran-2-ol 
• 121980-44-7 methyl (3R)-3-<(t-butyl)dimethylsilyloxy>hex-5-enoate 
• 121980-45-8 (3R)-(-)-methyl 3-<(tert-butyldimethylsilyl)oxy>-4-formylbutanoate 
• 121980-46-9 methyl (3R)-3-<(t-butyl)dimethylsilyloxy>-7-phenylhept-5-enoate 
• 121980-49-2 (R)-4-Hydroxy-6-(2-phenyl-1-phenylselanyl-ethyl)-tetrahydro-pyran-2-one 
• 109462-44-4 (R)-3-hydroxy-5-hexenoic acid methyl ester 
• 1443831-16-0 (2Z,5R,6E)-7-phenylhepta-2,6-diene-1,5-diol 
• 1743-31-3 (E)-1-phenylhex-1-en-5-yn-3-ol 
• 917251-09-3 tert-butyl-dimethyl-{3-phenyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-allyloxy}-silane 
• 917251-07-1 (3R)-1-phenyl-5-(tetrahydro-2H-2-pyranyloxy)-1-pentyl-3-ol 
• 917251-08-2 1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pent-1-en-3-ol 

Downstream Products

• 22639-28-7 (R)-goniothalamin 
• 122046-62-2 (S)-goniothalamin 
• 875433-92-4 (R)-6-[(E)-2-(2-nitrophenyl)ethenyl]-5,6-dihydro-2H-pyran-2-one 
• 146236-73-9 (+)-goniodiol 
• 122046-63-3 (6R)-6-[(2S,3S)-3-phenyloxiran-2-yl]-5,6-dihydro-2H-pyran-2-one 
• 875434-02-9 10-(N-α-tert-butoxycarbonyl-L-glutaminyl)aminogoniothalamin 
• 875434-03-0 (1-{2-[2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-phenylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 875434-01-8 ((1S,2S)-2-Methyl-1-{2-[(E)-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-phenylcarbamoyl}-butyl)-carbamic acid tert-butyl ester 
• 875434-00-7 (3-methyl-1-{2-[2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-phenylcarbamoyl}-butyl)-carbamic acid tert-butyl ester 
• 875433-99-1 (2-methyl-1-{2-[2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-phenylcarbamoyl}-propyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Annulation-retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products

A new and highly efficient annulation-retro-Claisen cascade, which involves the [4 + 1] or [5 + 1] annulation of α-benzoylacetates with bielectrophilic peroxides and a subsequent debenzoylation process under mild basic conditions, has been developed for the rapid construction of valuable tetrahydrofuran- and dihydropyran-2-carboxylates in good yields. By employing the new reaction, the unified total synthesis of γ- and δ-lactone natural products such as (±)-tanikolide, (±)-goniothalamins, (±)-7-epi-goniodiol, and (±)-plakolide A has been accomplished in 4-7 steps.

Synthesis and cytotoxic activities of goniothalamins and derivatives

Substituted goniothalamins containing cyclopropane-groups were efficiently prepared in high yields and good selectivity. Antiproliferative activity was measured on three human cancer cell lines (A549, MCF-7, HBL-100), to show which of the structural elements of goniothalamins is mandatory for cytotoxicity. We found that the configuration of the stereogenic centre of the δ-lactone plays an important role for cytotoxicity. In our studies only (R)-configured goniothalamins showed antiproliferative activity, whereby (R)-configuration accords to natural goniothalamin (R)-1. Additionally, the δ-lactone needs to be unsaturated whereas our results show that the vinylic double bond is not mandatory for cytotoxicity. Furthermore, with a two-fold in vitro and in vivo strategy, we determined the inhibitory effect of the compounds to the yeast protein Pdr5. Here, we clearly demonstrate that the configuration seems to be of minor influence, only, while the nature of the substituent of the phenyl ring is of prime importance.

Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e

A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72-75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot conversion of goniothalamin oxide to goniodiol or 9-deoxygoniopypyrone in aqueous media, stereoselective epoxidation, ring-closing metathesis, and stereoselective Maruoka allylation. The route is amenable to synthesis of various analogues for biological evaluation.