Eugenin

Catalog Number	ACM480342-1
CAS Number	480-34-2
Structure
Synonyms	5-Hydroxy-7-methoxy-2-methyl-4H-1-benzopyran 4-one
IUPAC Name	5-hydroxy-7-methoxy-2-methylchromen-4-one
Molecular Weight	206.19
Molecular Formula	C11H10O4
Canonical SMILES	O=C1C=C(C)OC2=C1C(O)=CC(OC)=C2
InChI	InChI=1S/C11H10O4/c1-6-3-8(12)11-9(13)4-7(14-2)5-10(11)15-6/h3-5,13H,1-2H3
InChI Key	SUTUBQHKZRNZRA-UHFFFAOYSA-N
Melting Point	118-119 °C
Purity	99%+
Appearance	White to off-white solid
Storage	-20 °C, Sealed storage, away from moisture and light In solvent: -80 °C, 6 months; -20 °C, 1 month (Sealed storage, away from moisture and light)
Complexity	297
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	0
Exact Mass	206.0579088
Heavy Atom Count	15
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	1
Monoisotopic Mass	206.0579088
PhysicalState	Powder
Rotatable Bond Count	1
Topological Polar Surface Area	55.8 Ų

Case Study

Distribution and Biological Activity of Eugenin

Nahar, Lutfun, et al. Phytochemistry Letters, 2024, 61, 191-197.

Eugenin (5-hydroxy-7-methoxy-2-methyl-4H-chromen-4-one) is a bioactive phytoalexin.
· Sources: Eugenin, which is produced through the acetate-malonate pathway, has been identified in 22 plant species from 13 different families as well as in two fungal species, Aschersonia confluens and Chaetomium minutum. The primary sources of this chromone are Dacaus carota and Syzygium aromaticum.
· Isolation and purification: Extracting eugenin from plant matrices is a relatively simple process that can be done using organic solvents such as ethanol and methanol in techniques like maceration, percolation, and Soxhlet. The compound is typically isolated using traditional methods like column chromatography, vacuum liquid chromatography, gel filtration, and solvent partitioning, with some studies also utilizing high-performance liquid chromatography.
· Biological activity: Various beneficial properties of eugenin have been documented, including antimalarial, antimicrobial, antioxidant, antiplatelet aggregation, antiviral, cytotoxic, immunosuppressive/immunomodulatory, osteogenesis-inducing, pyrolyl endopeptidase (PEP)-inhibitory, and blue-green algae growth inhibitory activities. Particularly, the antioxidant, antiplatelet aggregation, immunosuppressive/immunomodulatory capabilities of eugenin, as well as its potential antiviral effects against SARS-CoV-2 based on in silico predictions, could hold therapeutic promise.

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