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Details

Stereochemistry ACHIRAL
Molecular Formula C9H8O2
Molecular Weight 148.1586
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZODIHYDROPYRONE

SMILES

O=C1CCC2=C(O1)C=CC=C2

InChI

InChIKey=VMUXSMXIQBNMGZ-UHFFFAOYSA-N
InChI=1S/C9H8O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-4H,5-6H2

HIDE SMILES / InChI

Description

Dihydrocoumarin is a concentrated aromatic and flavor ingredient which may be used in flavor and fragrance compounds according to legal and IFRA or FEMA GRAS/FDA guidelines. Dihydrocoumarin is a common compound found in sweet clover that has been studied as a disruptor of epigenetic processes in cells. Epigenetic processes control gene expression within a cell and are highly influenced by environmental factors. Epigenomic disruptions change which genes are expressed and to what extent and are not linked to DNA mutations. Dihydrocoumarin has been shown to inhibit the sirtuin deacetylase family, specifically Sir2, SIRT1, and SIRT2.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
31.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Benzodihydropyrone produced little toxicity in rat hepatocytes in vivo (127 and 254 mg/kg, ip)
Route of Administration: Intraperitoneal
In Vitro Use Guide
Benzodihydropyrone at concentrations of