2-[5-(3-Methylbut-2-enoxy)-2-[3-[4-(3-methylbut-2-enoxy)phenyl]prop-2-enoyl]phenoxy]acetic acid
Basic information
- CAS
64506-49-6- Standard SMILES
CC(C)=CCOc1ccc(C=CC(=O)c2ccc(OCC=C(C)C)cc2OCC(=O)O)cc1- InChIKey
GFWRVVCDTLRWPK-UHFFFAOYSA-N- Molecular formula
- C27H30O6
- Average molar mass
- 450.5 g/mol
- Monoisotopic mass
- 450.20423867
Names & identifiers
- Preferred name
- 2-[5-(3-Methylbut-2-enoxy)-2-[3-[4-(3-methylbut-2-enoxy)phenyl]prop-2-enoyl]phenoxy]acetic acid
- IUPAC
- 2-[5-(3-methylbut-2-enoxy)-2-[3-[4-(3-methylbut-2-enoxy)phenyl]prop-2-enoyl]phenoxy]acetic acid
- English name
- Sofalcone
- Molecular formula
- C27H30O6
- Molecular weight
- 450.52
Names & synonyms
SCHEMBL40766orb1302400orb3141147s54502-[5-(3-methylbut-2-enoxy)-2-[3-[4-(3-methylbut-2-enoxy)phenyl]prop-2-enoyl]phenoxy]acetic acid{5-[(3-Methylbut-2-en-1-yl)oxy]-2-(3-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}prop-2-enoyl)phenoxy}acetic acidsolonisoprenylchalconesu88SofaconeSOFALCONESOFALCONE JP
Show more names
(E)-SofalconeMr. Method ketoneSofalcone USP/EP/BPSofalcone (Standard)
Database identifiers
- CAS
64506-49-6- PubChem CID
- 5249
- DTXSID
DTXSID5023586
Properties
Computed structural properties
- XLogP
- 6.2
- Topological polar surface area
- 82.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 12
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 706
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 143 · 143-144°
- Boiling point
- 478.6 °C · 478.6°C (rough estimate)
- Density
- 1.1362 · 1.1362 (rough estimate)
- refractive index
- 1.487 · 1.4870 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Solid
- pka
- 2.98 · 2.98±0.10(Predicted)
- color
- Light Yellow
- InChI
- InChI=1S/C27H30O6/c1-19(2)13-15-31-22-8-5-21(6-9-22)7-12-25(28)24-11-10-23(32-16-14-20(3)4)17-26(24)33-18-27(29)30/h5-14,17H,15-16,18H2,1-4H3,(H,29,30)
- InChIKey
- GFWRVVCDTLRWPK-UHFFFAOYSA-N
- SMILES
- C(O)(=O)COC1=CC(OC/C=C(\C)/C)=CC=C1C(=O)C=CC1=CC=C(OC/C=C(\C)/C)C=C1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 in mice, rats: >10 g/kg orally (Tarumoto)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
DescriptionSofalcone is a synthetic antiulcer agent related to sophoradin, the active principle of the Chinese medicinal plant, Sophora subprostata. It is suggested to act via a strengthening of the mucosal barrier through an increase in blood flow and stimulation of the synthesis of sulfated mucopolysaccharides.
UsesSofalcone is an anti-ulcer chalcone derivative. It blocks inflammation by suppressing the production of nitric oxide, TNF-α, and MCP-1 while inducing the expression of heme oxygenase-1 when used at 10-20 μM. Sofalcone (20-50 μM) induces VEGF expression in gastric epithelial cells and promotes gastric ulcer healing following eradication therapy for H. pylori.[Cayman Chemical]
UsesSofalcone is a substituted chalcone with anti-ulcer activity.
Additional notes
DefinitionChEBI: Sofalcone is a member of the class of chalcones that is benzene in which the hydrogens at positions 1,2 and 5 are replaced by carboxymethoxy, (1E)-1-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-3-oxoprop-1-en-3-yl, and (3-methylbut-2-en-1-yl)oxy groups, respectively. It is a gastrointestinal drug currently used for treatment of gastritis and gastric ulcers in Japan and South Korea. It has a role as an anti-ulcer drug, a gastrointestinal drug, a plant metabolite and an antibacterial agent. It is an aromatic ether, a monocarboxylic acid and a member of chalcones.
Related reactions
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Compound notes
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