115473-63-7

Basic information

• Product Name: rupestonic acid
• Synonyms: rupestonic acid;(5S,8S,8aS)-1,2,4,5,6,7,8,8a-Octahydro-3,8-dimethyl-alpha-methylene-2-oxo-5-azuleneacetic acid
• CAS NO: 115473-63-7
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.3175
• Mol File: 115473-63-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 438°Cat760mmHg
• Flash Point: 232.8°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 6.76E-09mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: rupestonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: rupestonic acid(115473-63-7)
• EPA Substance Registry System: rupestonic acid(115473-63-7)

Safety Data

• Hazardous Substances Data: 115473-63-7(Hazardous Substances Data)

Usage

Description

Rupestonic acid, a sesquiterpene lactone compound, is derived from the plant Artemisia rupestris. It is recognized for its diverse pharmacological properties, such as anti-inflammatory, anti-tumor, and antimicrobial activities. rupestonic acid's ability to inhibit the production of pro-inflammatory cytokines and enzymes, induce apoptosis, and disrupt bacterial cell membranes contributes to its potential as a therapeutic agent.

Uses

Used in Pharmaceutical Industry:
Rupestonic acid is used as an anti-inflammatory agent for its capacity to reduce the production of pro-inflammatory cytokines and enzymes, thereby alleviating inflammation.
Used in Oncology:
Rupestonic acid is utilized as an anti-tumor agent due to its ability to induce apoptosis and inhibit the proliferation of cancer cells, making it a potential candidate for cancer treatment.
Used in Antimicrobial Applications:
Rupestonic acid serves as an antimicrobial agent, leveraging its capability to disrupt bacterial cell membranes and inhibit the growth of certain pathogens, which is beneficial in combating infections.

InChI:InChI=1/C15H20O3/c1-8-4-5-11(9(2)15(17)18)6-13-10(3)14(16)7-12(8)13/h8,11-12H,2,4-7H2,1,3H3,(H,17,18)/t8-,11-,12-/m0/s1

Upstream product

• 1266545-65-6 tert-butyl (2S,3S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxypent-4-enoate 
• 1265592-06-0 tert-butyl (R,Z)-2-((3-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl)oxy)acetate 
• 106757-58-8 (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)prop-2-en-1-ol 
• 106757-56-6 (Z)-(-)-methyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 

Downstream Products

• 1020150-90-6 C₂₁H₂₄O₃ 
• 1220765-83-2 C₂₁H₂₂Cl₂O₃ 
• 1220765-85-4 C₂₁H₂₄O₄ 
• 1020150-92-8 C₂₃H₂₆O₅ 
• 1020150-93-9 C₂₃H₂₇NO₄ 
• 1220765-75-2 C₂₁H₂₃ClO₃ 
• 1020150-91-7 C₂₅H₃₂O₃ 
• 1220765-77-4 C₂₁H₂₃BrO₃ 
• 1220765-81-0 C₂₁H₂₃FO₃ 
• 1220765-87-6 C₂₂H₂₆O₃ 
• 1020151-03-4 C₃₁H₃₆N₂O₃ 
• 1020151-00-1 C₂₈H₃₈N₂O₃ 
• 1020151-04-5 C₃₁H₃₆N₂O₄ 
• 1020151-02-3 C₃₀H₃₄N₂O₃ 

Relevant articles and documents

Asymmetric Synthesis of Rupestonic Acid and Pechueloic Acid

In this report, the originally proposed rupestonic acid (5) and pechueloic acid (3) were efficiently synthesized. The chiral lactone 13, recycled from the degradation of saponin glycosides, was utilized to prepare the key chiral fragment 11. During the exploration of this convergent assembly strategy, the ring-closing metathesis (RCM), SmI2-prompted intermolecular addition, and [2,3]-Wittig rearrangement proved to be effective transformations for the synthesis of subunits.