29914-01-0

Basic information

• Product Name: (+)-Ramulosin
• Synonyms: (+)-Ramulosin;[3R,(+)]-3,4,4aβ,5,6,7-Hexahydro-3α-methyl-8-hydroxy-1H-2-benzopyran-1-one;Ramulosin
• CAS NO: 29914-01-0
• Molecular Formula: C10H14 O3
• Molecular Weight: 182.2164
• Mol File: 29914-01-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 309.2°Cat760mmHg
• Flash Point: 122.1°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 5.88E-05mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: (+)-Ramulosin(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Ramulosin(29914-01-0)
• EPA Substance Registry System: (+)-Ramulosin(29914-01-0)

Safety Data

• Hazardous Substances Data: 29914-01-0(Hazardous Substances Data)

Usage

General Description

(+)-Ramulosin is a natural cyclic monoterpenoid compound that can be found in various plant species. It is known for its potential pharmacological properties, including anti-inflammatory and anti-tumor activities. Studies have shown that (+)-Ramulosin exhibits inhibitory effects against the growth of cancer cells and has potential as an anti-cancer agent. Additionally, it has been found to possess antioxidant properties, which may be beneficial for reducing oxidative stress and protecting cells from damage. The compound's unique chemical structure and biological activities make it a promising candidate for further research and potential development as a therapeutic agent.

InChI:InChI=1/C10H14O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h6-7,12H,2-5H2,1H3

Upstream product

• 80963-28-6 6-carbethoxy-1,4-dioxaspiro<4.5>dec-6-ene 
• 129156-59-8 (3R,4aR)-6,7-Dibromo-8-hydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-isochromen-1-one 
• 104317-27-3 (3R,4aR,8R,8aS)-(+)-8-acetyl-3-methyl-3,4,4a,7,8,8a-hexahydroisocoumarin 
• 104317-26-2 (R)-1-methyl-3,5-hexadienyl 4-oxo-2-pentenoate 
• 104317-23-9 (R)-4,6-heptadien-2-ol THP ether 
• 49636-38-6 (R)-4,6-heptadien-2-ol 
• 104331-44-4 (3R,4aS,8R,8aS)-(+)-8-acetoxy-3-methyl-3,4,4a,5,6,7,8,8a-octahydroisocoumarin 
• 104317-29-5 (3R,4aS,8R,8aS)-(+)-8-acetyl-3-methyl-3,4,4a,5,6,7,8,8a-octahydroisocoumarin 
• 126680-92-0 Carbonic acid methyl ester 1-methyl-2-((1S,5R)-3-oxo-5-trimethylsilanyl-cyclohexyl)-ethyl ester 
• 129156-57-6 ((7S,9R)-9-Trimethylsilanyl-1,4-dioxa-spiro[4.5]dec-7-yl)-acetaldehyde 
• 129156-58-7 (3S,5R)-3-(2-Hydroxy-propyl)-5-trimethylsilanyl-cyclohexanone 
• 126680-91-9 1-((7S,9R)-9-Trimethylsilanyl-1,4-dioxa-spiro[4.5]dec-7-yl)-propan-2-ol 
• 126680-93-1 (+)-8-Hydroxy-3-methyl-6-trimethylsilyl-3,4,4a,5,6,7-hexahydroisocoumarin 
• 126680-88-4 ((1R,5R)-3-Oxo-5-trimethylsilanyl-cyclohexyl)-acetic acid ethyl ester 

Relevant articles and documents

Synthesis of (-)-mellein, (+)-ramulosin, and related natural products

(-)-Mellein, (+)-ramulosin, (-)-O-methylmellein, (-)-6-hydroxymellein, (-)-6-methoxymellein, and (+)-6-hydroxyramulosin were synthesized as optically active forms using one-pot esterification-Michael addition-aldol reaction of δ-hydroxy-α,β-unsaturated aldehyde and diketene as a key step.

Diastereoselective 1,4-addition of various nucleophiles to 5-trimethylsilyl-2-cyclohexenone: Synthesis of (+)-ramulosin

Base catalyzed reaction of active methylene compounds or oxygen catalyzed reaction of trialkylboranes via radical pathway with 5-trimethylsilyl-2-cyclohexenone (1) gave the corresponding products with modest to high (3:2- 20:1) diastereopurities. High dia

CHIRAL SYNTHESIS OF (R)-(-)-MELLEIN AND (3R,4aS)-(+)-RAMULOSIN

By employing an intramolecular Diels-Alder reaction as the key-step, (R)-(-)-mellein 1a (a metabolite of Aspergillus melleus) and (3R,4aS)-(+)-ramulosin 2 (a metabolite of Pestalotia ramulosa) were synthesised from ethyl(R)-3-hydroxybutanoate 3a.