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
| Molecular Formula | C9H8O2 |
| Molecular Weight | 148.1586 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| The flavoring agent dihydrocoumarin reverses epigenetic silencing and inhibits sirtuin deacetylases. | 2005 Dec |
|
| Piperazinobenzopyranones and phenalkylaminobenzopyranones: potent inhibitors of breast cancer resistance protein (ABCG2). | 2005 Nov 17 |
|
| 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 |
|
| Biocatalytic production of dihydrocoumarin from coumarin by Saccharomyces cerevisiae. | 2006 Aug 23 |
|
| Xenobiotic reductase A in the degradation of quinoline by Pseudomonas putida 86: physiological function, structure and mechanism of 8-hydroxycoumarin reduction. | 2006 Aug 4 |
|
| 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 |
|
| 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 |
|
| 8-Meth-oxy-3-(4-methyl-benzyl-idene)-6-(prop-1-en-yl)chroman-4-one. | 2007 Dec 6 |
|
| A simple feedback resistor switch keeps latent HIV from awakening. | 2007 Jan |
|
| 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 |
|
| 1-(4-Methoxy-phen-yl)-7-phenyl-3-(phenyl-selenylmeth-yl)perhydro-isoxazolo[2',3':1,2]pyrrolo[3,4-b]azetidine-6-spiro-2'-chroman-2,4'-dione. | 2008 Apr 16 |
|
| 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 |
|
| Chromone and chromanone derivatives as strand transfer inhibitors of HIV-1 integrase. | 2008 Jan |
|
| 4'-Methyl-3-(4-nitro-phen-yl)-4-phenyl-4,5,1',2',3',4'-hexa-hydro-spiro-[isoxazole-5,2'-naphthalen]-1'-one. | 2008 Jan 23 |
|
| Trimethyl lock: a stable chromogenic substrate for esterases. | 2008 Jan 31 |
|
| Improved synthesis and pharmacological evaluation of racemic 11 -demethylcalanolide A. | 2008 Jul |
|
| 2-(5,7-Dimeth-oxy-4-oxo-4H-chromen-2-yl)phenyl 4-toluene-sulfonate. | 2008 Jul 23 |
|
| Novel isocyanide-based four-component reaction: a facile synthesis of fully substituted 3,4-dihydrocoumarin derivatives. | 2008 Jun 19 |
|
| 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 |
|
| SIRT1 inhibition alleviates gene silencing in Fragile X mental retardation syndrome. | 2008 Mar 7 |
|
| Discovery, in vivo activity, and mechanism of action of a small-molecule p53 activator. | 2008 May |
|
| Asymmetric cycloadditions of o-quinone methides employing chiral ammonium fluoride precatalysts. | 2008 Nov 6 |
|
| 3-Benzyl-idene-6-methoxy-chroman-4-one. | 2008 Oct 9 |
|
| A chromanone alkaloid from Derris ovalifolia stem. | 2009 |
|
| Identification of potentially safe promising fungal cell factories for the production of polyketide natural food colorants using chemotaxonomic rationale. | 2009 Apr 27 |
|
| Determinants of variation in human serum paraoxonase activity. | 2009 Feb |
|
| Bacterial degradation of aromatic compounds. | 2009 Jan |
|
| Chromone and chromanone glucosides from Hypericum sikokumontanum and their anti-Helicobacter pylori activities. | 2009 Jan |
|
| Interaction between human serum esterases and environmental metal compounds. | 2009 Jul |
|
| 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 |
|
| 3-Methyl-4H-chromen-4-one. | 2010 Jun 5 |
|
| Phenylalanine-544 plays a key role in substrate and inhibitor binding by providing a hydrophobic packing point at the active site of insulin-regulated aminopeptidase. | 2010 Oct |
|
| Organocatalytic asymmetric tandem Michael addition-hemiacetalization: a route to chiral dihydrocoumarins, chromanes, and 4H-chromenes. | 2010 Oct 15 |
|
| 2-(4-Chloro-phen-yl)-6-meth-oxy-chroman-4-one. | 2010 Sep 11 |
|
| Lactonases with organophosphatase activity: structural and evolutionary perspectives. | 2010 Sep 6 |
|
| High-density real-time PCR-based in vivo toxicogenomic screen to predict organ-specific toxicity. | 2011 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:32:53 GMT 2023
by
admin
on
Fri Dec 15 15:32:53 GMT 2023
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| Record UNII |
NM5K1Y1BT2
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| Record Status |
Validated (UNII)
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| Record Version |
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JECFA EVALUATION |
DIHYDROCOUMARIN
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