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=CC=CC=C2O1
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 |
|---|---|---|
| High-density real-time PCR-based in vivo toxicogenomic screen to predict organ-specific toxicity. | 2011 |
|
| Organocatalytic asymmetric tandem Michael addition-hemiacetalization: a route to chiral dihydrocoumarins, chromanes, and 4H-chromenes. | 2010-10-15 |
|
| 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. | 2010-10 |
|
| 2-(4-Chloro-phen-yl)-6-meth-oxy-chroman-4-one. | 2010-09-11 |
|
| Lactonases with organophosphatase activity: structural and evolutionary perspectives. | 2010-09-06 |
|
| 3-Methyl-4H-chromen-4-one. | 2010-06-05 |
|
| Aminocatalytic asymmetric inverse-electron-demand aza-Diels-Alder reaction of N-Ts-1-aza-1,3-butadienes based on coumarin cores. | 2010-04-21 |
|
| The thioesterase Bhp is involved in the formation of beta-hydroxytyrosine during balhimycin biosynthesis in Amycolatopsis balhimycina. | 2010-01-25 |
|
| Modulation of carcinogen metabolizing enzymes by chromanone A; a new chromone derivative from algicolous marine fungus Penicillium sp. | 2009-11 |
|
| N'-tert-Butyl-N'-(3,5-dimethyl-benzo-yl)-2,2-dimethyl-4-oxochroman-6-carbo-hydrazide. | 2009-07-29 |
|
| Interaction between human serum esterases and environmental metal compounds. | 2009-07 |
|
| Identification of potentially safe promising fungal cell factories for the production of polyketide natural food colorants using chemotaxonomic rationale. | 2009-04-27 |
|
| Determinants of variation in human serum paraoxonase activity. | 2009-02 |
|
| Bacterial degradation of aromatic compounds. | 2009-01 |
|
| Chromone and chromanone glucosides from Hypericum sikokumontanum and their anti-Helicobacter pylori activities. | 2009-01 |
|
| A chromanone alkaloid from Derris ovalifolia stem. | 2009 |
|
| Synthesis and antimicrobial activity of 2-alkenylchroman-4-ones, 2-alkenylthiochroman-4-ones and 2-alkenylquinol-4-ones. | 2008-12-15 |
|
| Asymmetric cycloadditions of o-quinone methides employing chiral ammonium fluoride precatalysts. | 2008-11-06 |
|
| 3-Benzyl-idene-6-methoxy-chroman-4-one. | 2008-10-09 |
|
| A novel method for the synthesis of substituted 3,4-dihydrocoumarin derivatives via isocyanide-based three-component reaction. | 2008-08-10 |
|
| 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. | 2008-08 |
|
| 2-(5,7-Dimeth-oxy-4-oxo-4H-chromen-2-yl)phenyl 4-toluene-sulfonate. | 2008-07-23 |
|
| Improved synthesis and pharmacological evaluation of racemic 11 -demethylcalanolide A. | 2008-07 |
|
| Novel isocyanide-based four-component reaction: a facile synthesis of fully substituted 3,4-dihydrocoumarin derivatives. | 2008-06-19 |
|
| 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. | 2008-06-07 |
|
| Discovery, in vivo activity, and mechanism of action of a small-molecule p53 activator. | 2008-05 |
|
| 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. | 2008-04-16 |
|
| SIRT1 inhibition alleviates gene silencing in Fragile X mental retardation syndrome. | 2008-03-07 |
|
| Aging and anti-aging: unexpected side effects of everyday medication through sirtuin1 modulation. | 2008-02 |
|
| Trimethyl lock: a stable chromogenic substrate for esterases. | 2008-01-31 |
|
| 4'-Methyl-3-(4-nitro-phen-yl)-4-phenyl-4,5,1',2',3',4'-hexa-hydro-spiro-[isoxazole-5,2'-naphthalen]-1'-one. | 2008-01-23 |
|
| Chromone and chromanone derivatives as strand transfer inhibitors of HIV-1 integrase. | 2008-01 |
|
| Stereoselective synthesis of 4-dehydroxydiversonol employing enantioselective palladium-catalysed domino reactions. | 2008 |
|
| 8-Eth-oxy-3-(4-isopropyl-benzyl-idene)-6-methyl-chroman-4-one. | 2007-12-21 |
|
| 8-Meth-oxy-3-(4-methyl-benzyl-idene)-6-(prop-1-en-yl)chroman-4-one. | 2007-12-06 |
|
| Lack of evidence for allergenic properties of coumarin in a fragrance allergy mouse model. | 2007-12 |
|
| 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. | 2007-05 |
|
| Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines. | 2007-03-01 |
|
| A simple feedback resistor switch keeps latent HIV from awakening. | 2007-01 |
|
| An HIV feedback resistor: auto-regulatory circuit deactivator and noise buffer. | 2007-01 |
|
| Synthesis and biological evaluation of benzopyran analogues bearing class III antiarrhythmic pharmacophores. | 2006-10-01 |
|
| Biocatalytic production of dihydrocoumarin from coumarin by Saccharomyces cerevisiae. | 2006-08-23 |
|
| Xenobiotic reductase A in the degradation of quinoline by Pseudomonas putida 86: physiological function, structure and mechanism of 8-hydroxycoumarin reduction. | 2006-08-04 |
|
| Inhibition of SIRT1 reactivates silenced cancer genes without loss of promoter DNA hypermethylation. | 2006-03 |
|
| Isolation, structure elucidation, antioxidative and immunomodulatory properties of two novel dihydrocoumarins from Aloe vera. | 2006-02-15 |
|
| Structure-Activity Relationships of Synthetic Coumarins as HIV-1 Inhibitors. | 2006 |
|
| The flavoring agent dihydrocoumarin reverses epigenetic silencing and inhibits sirtuin deacetylases. | 2005-12 |
|
| Stable isotope characterization of the ortho-oxygenated phenylpropanoids: coumarin and melilotol. | 2005-11-30 |
|
| Piperazinobenzopyranones and phenalkylaminobenzopyranones: potent inhibitors of breast cancer resistance protein (ABCG2). | 2005-11-17 |
|
| New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101. | 1997-03 |
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
JECFA EVALUATION |
DIHYDROCOUMARIN
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
100000142138
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
1162
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
10121
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
C026308
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
SUB115711
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
204-354-9
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
16151
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
DTXSID2020474
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
119-84-6
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
NM5K1Y1BT2
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
660
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY | |||
|
4333
Created by
admin on Mon Mar 31 18:00:46 GMT 2025 , Edited by admin on Mon Mar 31 18:00:46 GMT 2025
|
PRIMARY |
SUBSTANCE RECORD
