| Identification | More | [Name]
Sieber Linker | [CAS]
3722-51-8 | [Synonyms]
3-HYDROXY-XANTHEN-9-ONE
3-HYDROXYXANTHONE
6-HYDROXY-3-FLUORONE
HF
SALOR-INT L254835-1EA
SIEBER LINKER
3-Hydroxy-9H-xanthen-9-one
SIEBER LINKER,3-HYDROXY-XANTHEN-9-ONE
3-HYDROXY-XANTHEN-9-ONE SIEBER LINKER 99+%
SIEBER LINKER, 99% MIN. | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C13H8O3 | [MDL Number]
MFCD06796485 | [Molecular Weight]
212.2 | [MOL File]
3722-51-8.mol |
| Questions And Answer | Back Directory | [Synthesis]
In a 2L three-necked flask, add 140.1g of o-fluorobenzoic acid and 1000ml of dichloromethane, then add 138.2g of m-phenylenediamine. Cool to 5-10℃, and slowly add 133.3g of anhydrous aluminum trichloride. The system gradually releases a large amount of heat. Control the temperature below 10℃ and slowly add the aluminum trichloride. The system will gradually precipitate from a yellowish-brown clear liquid to a yellowish-brown solid. Remove the ice bath and react at room temperature for 6 hours. TLC monitoring shows that the o-fluorobenzoic acid is almost completely consumed. After the reaction was completed and cooled to below 5°C, the system was slowly added to 500g of ice water to quench the reaction. During this process, a large amount of heat was released and gas was released. After quenching, 500ml of 6N hydrochloric acid was added and stirred for 10 minutes. The mixture was separated, and the resulting organic phase was washed once with 500ml of saturated sodium bicarbonate solution. The mixture was then separated, and the organic phase was washed once with 500ml of saturated sodium chloride solution. The mixture was then separated, dried with anhydrous magnesium sulfate, decolorized with activated carbon, and filtered to obtain a pale yellow liquid. The liquid was then vortexed until a large amount of white solid precipitated. 2L of petroleum ether was added and the mixture was stirred in an ice bath for 1 hour. The mixture was then filtered to obtain a white solid, which was dried under vacuum to obtain 210g of intermediate (single-step molar yield 80.7%, melting point around 80°C). In a 2L three-necked flask, 210g of the intermediate and 1200g of hydrobromic acid aqueous solution were added. Under nitrogen protection, the mixture was heated to 95℃ and reacted for approximately 8 hours. During this time, the solid gradually dissolved into a clear yellow liquid, and the color of the system deepened with increasing reaction time. TLC monitoring confirmed the absence of the intermediate, and the reaction was considered complete. The system was concentrated, precipitating a large amount of pale yellow crude solid. The crude solid was dissolved in 1500ml of ethanol under reflux, decolorized with activated carbon, and filtered. The resulting filtrate was cooled to room temperature, and 3000ml of water was added to slurry the mixture. Filtering yielded a white to white solid, which was then vacuum dried to obtain 145.5g of the product, Siber linkage agent (single-step molar yield 85.1%, HPLC: 98.6%, melting point: 251-253℃). 
The reaction products were characterized by nuclear magnetic resonance (NMR), and the data are as follows: H NMR (400MHz, DMSO): δ6.89(d, 1H), δ6.92(dd, 1H), δ7.46(td, 1H), δ7.63(d, 1H), δ7.77(td, 1H), δ8.02(d, 1H), δ8.12(dd, 1H), δ11(br, OH) |
| Chemical Properties | Back Directory | [Melting point ]
243 °C | [Boiling point ]
403.9±24.0 °C(Predicted) | [density ]
1.395±0.06 g/cm3(Predicted) | [storage temp. ]
Store at 0°C | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Solid | [pka]
7.52±0.20(Predicted) | [color ]
White to Orange to Green | [Detection Methods]
HPLC | [InChI]
InChI=1S/C13H8O3/c14-8-5-6-10-12(7-8)16-11-4-2-1-3-9(11)13(10)15/h1-7,14H | [InChIKey]
XCJHDJAODLKGLG-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C=CC=C2)OC2=C1C=CC(O)=C2 | [CAS DataBase Reference]
3722-51-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315-H319 | [Precautionary statements ]
P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white or grey powder | [Uses]
Sieber linker (3-Hydroxyxanthen-9-one,3722-51-8) is a natural product of the trifluoroacetic acid group found in Hypericum sampsonii and Rhachidosorus mesosorus. It has antiplatelet and anti-inflammatory properties. It also inhibits the expression of tumour necrosis factor-α (TNF-α) in mice. The synthesis of TNF-α is inhibited by Sieber linker, which may be due to its ability to inhibit the enzyme phosphodiesterase 4 (PDE4). Sieber linker also inhibits the binding of PDL1 to dinucleotide phosphate (DNP) and has an inhibitory effect on cancer cells. This molecule can be used for the treatment of infectious diseases, such as malaria and tuberculosis, since it inhibits protein synthesis in bacteria.
| [Synthesis Reference(s)]
Tetrahedron, 43, p. 3075, 1987 DOI: 10.1016/S0040-4020(01)86849-6 | [Purification Methods]
Purify the xanthone by chromatography on SiO2 gel with pet ether/*benzene as eluent. Recrystallise it from *benzene or EtOH. The acetate has m 157-158o. [Itoh et al. J Am Chem Soc 107 4819 1985, Davies et al. J Org Chem 23 307 1958]. [Beilstein 18 H 46, 18 I 315, 18 II 29, 21 III/IV 601.] |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
New Energy Chemicals
|
| Telephone: |
0515-82159099 13770142076 |
| Website: |
http://www.njuchem.com/ |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|