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Basic information
- CAS
3722-51-8- Standard SMILES
O=c1c2ccccc2oc2cc(O)ccc12- InChIKey
XCJHDJAODLKGLG-UHFFFAOYSA-N- Molecular formula
- C13H8O3
- Average molar mass
- 212.204 g/mol
- Monoisotopic mass
- 212.04734412
Names & identifiers
- Preferred name
- 3-Hydroxyxanthen-9-one
- IUPAC
- 3-Hydroxy-9H-xanthen-9-one
- English name
- Sieber Linker
- Molecular formula
- C13H8O3
- Molecular weight
- 212.2
Names & synonyms
HF3-Hydroxy-9H-xanthen-9-oneSibur linkerSIEBER LINKERSieber Linkers3-HYDROXYXANTHONE6-HYDROXY-3-FLUORONESALOR-INT L254835-1EA3-HYDROXY-XANTHEN-9-ONESIEBER LINKER, 99% MIN.
Database identifiers
- CAS
3722-51-8- PubChem CID
- 5376013
- DTXSID
DTXSID30418770- ChEMBL
CHEMBL365640- EC Number
- 126-475-5
- Nikkaji
- J130.932C
Properties
Physicochemical properties
- Melting point
- 243 °C · 243 °C
- Boiling point
- 403.9 · 403.9±24.0 °C(Predicted)
- Density
- 1.395 · 1.395±0.06 g/cm3(Predicted)
- storage temp.
- 0 °C · Store at 0°C
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- pka
- 7.52 · 7.52±0.20(Predicted)
- form
- Solid
- color
- White to Orange to Green
- 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 · 3722-51-8(CAS DataBase Reference)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319
- Precautionary statements
- 305 · P305+P351+P338
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- HS Code
- 29329900 · 29329900
Safety & regulation
Safety data
- hs_code
- 29329900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard statements
- H302-H315-H319
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Applications
UsesSieber linker (3-Hydroxyxanthen-9-one) 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.
Upstream & downstream products
Upstream raw materials
Related reactions
6 records
Compound notes
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