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
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
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101. | 1997 Mar |
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| Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
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| Lactone-ring-cleaving enzymes of microorganisms: their diversity and applications. | 2001 Dec 28 |
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| Synthesis of 3-methoxycarbonylmethyl derivatives of dihydroquinolone and dihydrochromenone. | 2001 Mar 23 |
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| Electrolytic partial fluorination of organic compounds. 55. Highly regio- and stereoselective anodic monofluorination of 2,3-dihydrochroman-4-one and chromone derivatives. | 2001 Nov 16 |
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| Hericenols A-D and a chromanone from submerged cultures of a Stereum species. | 2002 Jun |
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| Synthesis and oxidation behavior of 2,4,5,7,8-pentamethyl-4H-1,3-benzodioxin-6-ol, a multifunctional oxatocopherol-type antioxidant. | 2002 May 31 |
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| Role of Acinetobacter calcoaceticus 3,4-dihydrocoumarin hydrolase in oxidative stress defence against peroxoacids. | 2003 Feb |
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| Mouse macrophage paraoxonase 2 activity is increased whereas cellular paraoxonase 3 activity is decreased under oxidative stress. | 2003 Mar 1 |
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| New chromanone acids with antibacterial activity from Calophyllum brasiliense. | 2004 Apr |
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| Chromanones and dihydrocoumarins from Calophyllum blancoi. | 2004 Apr |
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| Senescence marker protein-30 is a unique enzyme that hydrolyzes diisopropyl phosphorofluoridate in the liver. | 2004 Jul 16 |
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| A simple radical addition-elimination route to geometrically pure (E)-alkene and chromanone derivatives via beta-nitrostyrene. | 2004 May 28 |
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| Halogenation of drugs enhances membrane binding and permeation. | 2004 May 3 |
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| Antioxidant dehydrotocopherols as a new chemical character of Stemona species. | 2004 Oct |
|
| Stable isotope characterization of the ortho-oxygenated phenylpropanoids: coumarin and melilotol. | 2005 Nov 30 |
|
| Structure-Activity Relationships of Synthetic Coumarins as HIV-1 Inhibitors. | 2006 |
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| Biocatalytic production of dihydrocoumarin from coumarin by Saccharomyces cerevisiae. | 2006 Aug 23 |
|
| Isolation, structure elucidation, antioxidative and immunomodulatory properties of two novel dihydrocoumarins from Aloe vera. | 2006 Feb 15 |
|
| Inhibition of SIRT1 reactivates silenced cancer genes without loss of promoter DNA hypermethylation. | 2006 Mar |
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| Synthesis and biological evaluation of benzopyran analogues bearing class III antiarrhythmic pharmacophores. | 2006 Oct 1 |
|
| Lack of evidence for allergenic properties of coumarin in a fragrance allergy mouse model. | 2007 Dec |
|
| 8-Eth-oxy-3-(4-isopropyl-benzyl-idene)-6-methyl-chroman-4-one. | 2007 Dec 21 |
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| An HIV feedback resistor: auto-regulatory circuit deactivator and noise buffer. | 2007 Jan |
|
| Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines. | 2007 Mar 1 |
|
| Transcriptome and proteome analyses in response to 2-methylhydroquinone and 6-brom-2-vinyl-chroman-4-on reveal different degradation systems involved in the catabolism of aromatic compounds in Bacillus subtilis. | 2007 May |
|
| Stereoselective synthesis of 4-dehydroxydiversonol employing enantioselective palladium-catalysed domino reactions. | 2008 |
|
| Spectroscopic characterization of the 1-substituted 3,3-diphenyl-4-(2'-hydroxyphenyl)azetidin-2-ones: application of (13)C NMR, (1)H-(13)C COSY NMR and mass spectroscopy. | 2008 Aug |
|
| A novel method for the synthesis of substituted 3,4-dihydrocoumarin derivatives via isocyanide-based three-component reaction. | 2008 Aug-Nov |
|
| Synthesis and antimicrobial activity of 2-alkenylchroman-4-ones, 2-alkenylthiochroman-4-ones and 2-alkenylquinol-4-ones. | 2008 Dec 15 |
|
| Aging and anti-aging: unexpected side effects of everyday medication through sirtuin1 modulation. | 2008 Feb |
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| Chromone and chromanone derivatives as strand transfer inhibitors of HIV-1 integrase. | 2008 Jan |
|
| Trimethyl lock: a stable chromogenic substrate for esterases. | 2008 Jan 31 |
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| Improved synthesis and pharmacological evaluation of racemic 11 -demethylcalanolide A. | 2008 Jul |
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| 2-(5,7-Dimeth-oxy-4-oxo-4H-chromen-2-yl)phenyl 4-toluene-sulfonate. | 2008 Jul 23 |
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| Novel isocyanide-based four-component reaction: a facile synthesis of fully substituted 3,4-dihydrocoumarin derivatives. | 2008 Jun 19 |
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| rac-(1S,2R)-Diethyl 6-hydr-oxy-1-(4-methoxy-phen-yl)-3-oxo-2,3-di-hydro-1H-benzo[f]chromen-2-yl]-phospho-nate. | 2008 Jun 7 |
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| SIRT1 inhibition alleviates gene silencing in Fragile X mental retardation syndrome. | 2008 Mar 7 |
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| Discovery, in vivo activity, and mechanism of action of a small-molecule p53 activator. | 2008 May |
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| Asymmetric cycloadditions of o-quinone methides employing chiral ammonium fluoride precatalysts. | 2008 Nov 6 |
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| 3-Benzyl-idene-6-methoxy-chroman-4-one. | 2008 Oct 9 |
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| A chromanone alkaloid from Derris ovalifolia stem. | 2009 |
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| Determinants of variation in human serum paraoxonase activity. | 2009 Feb |
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| N'-tert-Butyl-N'-(3,5-dimethyl-benzo-yl)-2,2-dimethyl-4-oxochroman-6-carbo-hydrazide. | 2009 Jul 29 |
|
| Modulation of carcinogen metabolizing enzymes by chromanone A; a new chromone derivative from algicolous marine fungus Penicillium sp. | 2009 Nov |
|
| Aminocatalytic asymmetric inverse-electron-demand aza-Diels-Alder reaction of N-Ts-1-aza-1,3-butadienes based on coumarin cores. | 2010 Apr 21 |
|
| The thioesterase Bhp is involved in the formation of beta-hydroxytyrosine during balhimycin biosynthesis in Amycolatopsis balhimycina. | 2010 Jan 25 |
|
| High-density real-time PCR-based in vivo toxicogenomic screen to predict organ-specific toxicity. | 2011 |
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JECFA EVALUATION |
DIHYDROCOUMARIN
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SUBSTANCE RECORD
