Xanthatin
| Names | |
|---|---|
| IUPAC name
(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
| |
| Properties | |
| C15H18O3 | |
| Molar mass | 246.306 g/mol |
| Appearance | White crystalline solid |
| Density | 1.241 g/cm3 (21.84 °C)[1] |
| Melting point | 114–115 °C (237–239 °F; 387–388 K) [2] |
| Boiling point | Decomposes |
| Slightly soluble | |
| Solubility | Soluble in acetone, chloroform, dichloromethane, ethyl acetate, methanol |
| Vapor pressure | ~0 mmHg |
| Hazards | |
| Safety data sheet | MedChemExpress |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Xanthatin is a major bioactive compound found in the leaves of the Xanthium strumarium (Asteracae) plant. It is classified as a natural sesquiterpene lactone.
Contents
Properties
Chemical
Xanthatin will react with halogens.
Physical
Xanthatin is a white clear colorless solid, soluble in organic solvents. It is poorly soluble in cold water, but more soluble in hot water.
Availability
Xanthatin is produced by the Xanthium strumarium plant.
It can be extracted from the dried leaves of this plant, which contain around 20% xanthatin, as well as other similar compounds. Chloroform can be used as the extraction solvent, but other solvents like dichloromethane, methanol or acetone can also be used.[3][4]
Lastly, it can be bought from chemical suppliers, but it's expensive.
Preparation
The total synthesis of this compound requires multiple steps.[5]
Projects
- Compound collecting
- Potential use in medicine
Handling
Safety
Xanthatin is believed to have anti-inflammatory, anti-tumour, anti-microbial, and anti-parasitic properties hence it is being researched for potential use in treatment of cancer and autoimmune diseases. While it has been used in traditional Chinese medicine for decades, its mechanisms and modern use haven’t been fully understood yet.
At high concentrations, xanthatin exhibits hepatotoxic effects, causing liver damage in mice.
Storage
In airtight containers, away from light and corrosive reagents.
Disposal
No special disposal is required.
References
- ↑ Shang, Hai; Liu, Junhua; Bao, Ruiyang; Cao, Yu; Zhao, Kun; Xiao, Chengqian; Zhou, Bing; Hu, Lihong; Tang, Yefeng; Angewandte Chemie - International Edition; vol. 53; nb. 52; (2014); p. 14494 - 14498; Angew. Chem.; vol. 126; nb. 52; (2014); p. 14722 - 14726,4
- ↑ He, Yuan; Lei, Dongyu; Yang, Qingqing; Qi, Hao; Almira, Kurax; Askar, Dilnigar; Jin, Lu; Pan, Le; Natural Product Research; vol. 35; nb. 14; (2021); p. 2433 - 2437
- ↑ McMillan C, Chavez PI, Mabry TJ (October 1975). "Sesquiterpene lactones of Xanthium strumarium in a texas population and in experimental hybrids". Biochemical Systematics and Ecology. 3 (3): 137–141
- ↑ He, Yuan; Lei, Dongyu; Yang, Qingqing; Qi, Hao; Almira, Kurax; Askar, Dilnigar; Jin, Lu; Pan, Le; Natural Product Research; vol. 35; nb. 14; (2021); p. 2433 - 2437
- ↑ Yokoe H, Yoshida M, Shishido K (May 2008). "Total synthesis of (−)-xanthatin". Tetrahedron Letters. 49 (21): 3504–3506
