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dihydrocoumarin

Chemical Structure

General Material Information

Preferred name dihydrocoumarin
Trivial Name Dihydrocoumarin
Short Description 3,4-dihydrocoumarin
Formula C9 H8 O2
CAS Number 119-84-6
Deleted CAS Number 1341-36-2
FEMA Number 2381
Flavis Number 13.009
ECHA Number 204-354-9
FDA UNII NM5K1Y1BT2
Nikkaji Number J36.832F
Beilstein Number 0004584
MDL MFCD00006881
COE Number 535
xLogP3-AA 1.60 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1171 dihydrocoumarin
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 119-84-6 ; DIHYDROCOUMARIN
Synonyms
  • benzo dihydro pyrone
  • benzo dihydropyrone
  • benzo dihydropyrone natural
  • benzo dihydropyrone synthetic
  • benzodihydropyrone
  • 1,2-benzodihydropyrone
  • benzodihydropyrone FCC
  • benzodihydropyrone, natural
  • 2H-1-benzopyran-2-one, 3,4-dihydro-
  • benzopyranone, dihydro-
  • 2-oxo- chroman
  • oxo chroman
  • chroman-2-one
  • chroman, 2-oxo-
  • 2-chromanone
  • coumarin, 3,4-dihydro-
  • coumarin, dihydro-
  • di hydro coumarin
  • dihydro coumarin
  • 3,4-dihydro-1-benzopyran-2-one
  • 3,4-dihydro-2H-1-benzopyran-2-one
  • 3,4-dihydro-2H-chromen-2-on
  • 3,4-dihydro-2H,1-benzopyran-2-one
  • dihydrobenzopyrone
  • 3,4-dihydrocoumarin
  • dihydrocoumarin (benzodihydropyrone)
  • dihydrocoumarin FCC
  • hydrocinnamic acid, o-hydroxy-, d-lactone
  • hydrocoumarin
  • o- hydroxydihydrocinnamic acid delta-lactone
  • ortho- hydroxydihydrocinnamic acid delta-lactone
  • 2-hydroxydihydrocinnamic acid lactone
  • hydroxydihydrocinnamic acid lactone, o-
  • melilotic acid lactone
  • melilotic lactone
  • melilotin
  • melilotine
  • melilotol
  • meliotine
  • 2H-1-Benzopyran-2-one, 3,4-dihydro-
  • 3,4-Dihydro-2H-1-benzopyran-2-one
  • Hydrocinnamic acid, o-hydroxy-, δ-lactone
  • 2-Chromanone
  • Melilotin (coumarin)
  • 3,4-Dihydrocoumarin
  • 3,4-Dihydro-1H-benzopyran-2-one
  • D 1223
  • DHC
  • 3,4-Dihydrochromen-2-one

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

chroman-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:119-84-6
Pubchem (cid):660
Pubchem (sid):134974732
Publications by Info
EVALUATION OF CERTAIN FOOD ADDITIVES AND CONTAMINANTS
Publications by PubMed
Tandem ruthenium-catalyzed transfer-hydrogenative cyclization/intramolecular Diels-Alder reaction of enediynes affording dihydrocoumarin-fused polycycles.
Study of possible mechanisms involved in the inhibitory effects of coumarin derivatives on neutrophil activity.
Effect of the nutritional supplement ALAnerv® on the serum PON1 activity in post-acute stroke patients.
Serum lactonase and arylesterase activities in alcoholic hepatitis and hepatitis B.
N-heterocyclic carbene-catalyzed [4 + 2] cycloaddition of ketenes and 3-aroylcoumarins: highly enantioselective synthesis of dihydrocoumarin-fused dihydropyranones.
Cancer chemoprevention and nutriepigenetics: state of the art and future challenges.
Synthesis and biological evaluation of α-methylidene-δ-lactones with 3,4-dihydrocoumarin skeleton.
[Determination of five coumarins in toys by high performance liquid chromatography-tandem mass spectrometry].
Novel associations of nonstructural Loci with paraoxonase activity.
Oxidative potential of some endophytic fungi using 1-indanone as a substrate.
Catalytic versatility and backups in enzyme active sites: the case of serum paraoxonase 1.
Facile synthesis of 4-substituted 3,4-dihydrocoumarins via an organocatalytic double decarboxylation process.
An enantioselective approach toward 3,4-dihydroisocoumarin through the bromocyclization of styrene-type carboxylic acids.
High-Density Real-Time PCR-Based in Vivo Toxicogenomic Screen to Predict Organ-Specific Toxicity.
Asymmetric synthesis of 3,4-dihydrocoumarin motif with an all-carbon quaternary stereocenter via a Michael-acetalization sequence with bifunctional amine-thiourea organocatalysts.
Atom arrangement strategy for designing a turn-on 1H magnetic resonance probe: a dual activatable probe for multimodal detection of hypochlorite.
Chemical composition, anti-inflammatory, molluscicidal and free-radical scavenging activities of the leaves of Ficus radicans 'Variegata' (Moraceae).
Development and validation of two methods based on high-performance liquid chromatography-tandem mass spectrometry for determining 1,2-benzopyrone, dihydrocoumarin, o-coumaric acid, syringaldehyde and kaurenoic acid in guaco extracts and pharmaceutical preparations.
Coumarin metabolic routes in Aspergillus spp.
Paraoxonase 2 (PON2) in the mouse central nervous system: a neuroprotective role?
Synthesis and biological activity of splitomicin analogs targeted at human NAD(+)-dependent histone deacetylases (sirtuins).
Different effect of two synthetic coumarin-stilbene hybrid compounds on phagocyte activity.
Cancer chemoprevention by targeting the epigenome.
Organocatalytic asymmetric tandem Michael addition-hemiacetalization: a route to chiral dihydrocoumarins, chromanes, and 4H-chromenes.
A reinvestigation of the reaction of coumarins with superoxide in the liposomal bilayer: correlation between depth and reactivity.
Lactonases with organophosphatase activity: structural and evolutionary perspectives.
The thioesterase Bhp is involved in the formation of beta-hydroxytyrosine during balhimycin biosynthesis in Amycolatopsis balhimycina.
Interaction between human serum esterases and environmental metal compounds.
Determinants of variation in human serum paraoxonase activity.
Asymmetric cycloadditions of o-quinone methides employing chiral ammonium fluoride precatalysts.
A novel method for the synthesis of substituted 3,4-dihydrocoumarin derivatives via isocyanide-based three-component reaction.
Synthesis, spectroscopy and alkylating properties of Pd(II) complexes of phosphorohydrazones of coumarin and chromone with potential antibacterial activity.
Novel isocyanide-based four-component reaction: a facile synthesis of fully substituted 3,4-dihydrocoumarin derivatives.
AlCl3-mediated direct carbon-carbon bond-forming reaction of alpha-hydroxyketene-S,S-acetals with arenes and synthesis of 3,4-disubstituted dihydrocoumarin derivatives.
Aging and anti-aging: unexpected side effects of everyday medication through sirtuin1 modulation.
Lack of evidence for allergenic properties of coumarin in a fragrance allergy mouse model.
Biocatalytic production of dihydrocoumarin from coumarin by Saccharomyces cerevisiae.
Xenobiotic reductase A in the degradation of quinoline by Pseudomonas putida 86: physiological function, structure and mechanism of 8-hydroxycoumarin reduction.
The flavoring agent dihydrocoumarin reverses epigenetic silencing and inhibits sirtuin deacetylases.
Isolation, structure elucidation, antioxidative and immunomodulatory properties of two novel dihydrocoumarins from Aloe vera.
Cloning, purification, and refolding of human paraoxonase-3 expressed in Escherichia coli and its characterization.
Cloning, high level expression of human paraoxonase-3 in Sf9 cells and pharmacological characterization of its product.
Regioselective synthesis and estrogenicity of (+/-)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins.
Senescence marker protein-30 is a unique enzyme that hydrolyzes diisopropyl phosphorofluoridate in the liver.
Chromanones and dihydrocoumarins from Calophyllum blancoi.
Mouse macrophage paraoxonase 2 activity is increased whereas cellular paraoxonase 3 activity is decreased under oxidative stress.
Role of Acinetobacter calcoaceticus 3,4-dihydrocoumarin hydrolase in oxidative stress defence against peroxoacids.
Enzymatic preparation of D-beta-acetylthioisobutyric acid and cetraxate hydrochloride using a stereo- and/or regioselective hydrolase, 3,4-dihydrocoumarin hydrolase from Acinetobacter calcoaceticus.
Coupling of the lactone-ring conformation with crystal symmetry in 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin.
Lactone-ring-cleaving enzymes of microorganisms: their diversity and applications.
Purification and characterization of a novel lactonohydrolase from Agrobacterium tumefaciens.
3,4-Dihydrocoumarin hydrolase with haloperoxidase activity from Acinetobacter calcoaceticus F46.
A "cephalosporin-like" cyclic depsipeptide: synthesis and reaction with beta-lactam-recognizing enzymes.
Selective Clara cell injury in mouse lung following acute administration of coumarin.
Intraperitoneal administration of coumarin causes tissue-selective depletion of cytochromes P450 and cytotoxicity in the olfactory mucosa.
Inhibition of the mutagenicity of 2-nitrofluorene, 3-nitrofluoranthene and 1-nitropyrene by flavonoids, coumarins, quinones and other phenolic compounds.
New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101.
Natural ingredients based cosmetics. Content of selected fragrance sensitizers.
Structure-activity relationship of coumarins in xanthine oxidase inhibition.
HPLC analysis of tonka bean extracts.
Comparison of the hepatic effects of coumarin, 3,4-dimethylcoumarin, dihydrocoumarin and 6-methylcoumarin in the rat.
NTP Toxicology and Carcinogenesis Studies of Coumarin (CAS No. 91-64-5) in F344/N Rats and B6C3F1 Mice (Gavage Studies).
NTP Toxicology and Carcinogenesis Studies of 3,4-Dihydrocoumarin (CAS No. 119-84-6) in F344/N Rats and B6C3F1 Mice (Gavage Studies).
Structural requirements for the direct and cytochrome P450-dependent reaction of cyclic alpha,beta-unsaturated carbonyl compounds with glutathione: a study with coumarin and related compounds.
Purification and characterization of a novel lactonohydrolase, catalyzing the hydrolysis of aldonate lactones and aromatic lactones, from Fusarium oxysporum.
Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring fission products.
Toxicity of coumarin and various methyl derivatives in cultures of rat hepatocytes and V79 cells.
Anamnestic responses to contact allergens: application in the murine local lymph node assay.
Amine prodrugs which utilize hydroxy amide lactonization. II. A potential esterase-sensitive amide prodrug.
Acyloxybenzyl halides, inhibitors of elastases.
A prospective toxicity evaluation (COMPACT) on 40 chemicals currently being tested by the National Toxicology Program.
Reaction of thrombin and proteinases of the fibrinolytic system with a mechanism-based inhibitor, 3,4-dihydro-3-benzyl-6-chloromethylcoumarin.
Studies on the mechanism of coumarin-induced toxicity in rat hepatocytes: comparison with dihydrocoumarin and other coumarin metabolites.
Constituents of Justicia pectoralis Jacq. 2. Gas chromatography/mass spectrometry of simple coumarins, 3-phenylpropionic acids and their hydroxy and methoxy derivatives.
The sensitizing capacity of coumarins (II).
The epicutaneous maximization test.
Inactivation of human high- and low-molecular-weight urokinases. Analysis of their active site.
Reactions in selected patients to 22 fragrance materials.
Comparative study of methods chosen by the Association Française de Normalisation (AFNOR) for evaluating sensitizing potential in the albino guinea-pig.
Degradation of 3-phenylbutyric acid by Pseudomonas sp.
Further studies of effects of vehicles and elicitation concentration in experimental contact sensitization testing in humans.
Physiologically active substances from marine sponges V: Isolation of physiologically active compounds from the sponge Verongia archeri.
The metabolism of aromatic compounds in higher plants. V. Purification and properties of dihydrocoumarin hydrolase of Melilotus alba.
[Application of Baeyer-Villiger reaction in synthesis of dihydrocoumarin].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C02274
HMDB (The Human Metabolome Database):HMDB36626
FooDB:FDB015543
Export Tariff Code:2932.20.4500
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 148.16116333008
Specific gravity @ 25 °C
Pounds per Gallon 9.869 to 9.919
Refractive Index 1.54 to 1.58 @ 20 °C
Melting Point 24 to 25°C @ 760 mm Hg
Boiling Point 271 to 272°C @ 760 mm Hg
Acid Value 5 max KOH/g
Vapor Pressure 4 mmHg @ 25 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 2.428 est
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
water, 3000 mg/L @ 37 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Tonka
sweet, tonka, coumarinic, coconut, herbal, cinnamon, balsamic, creamy, vanilla, spicy
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 228 hour(s) at 100.00 %
Luebke, William tgsc, (1987) At 10.00 % in dipropylene glycol. sweet tonka coumarinic coconut herbal cinnamon balsamic
Mosciano, Gerard P&F 17, No. 3, 57, (1992) Sweet, creamy, coconut, coumarin, vanilla with a slight spice nuance
Flavor Type: Creamy
creamy, coconut, coumarinic, vanilla, cinnamyl, balsamic, spicy, cardamom, sweet, milky
Luebke, William tgsc, (1987) Creamy coconut coumarinic vanilla cinnamyl balsamic spicy cardamom
Mosciano, Gerard P&F 17, No. 3, 57, (1992) At 10.00 ppm. Sweet, creamy, vanilla, coconut and milky
General comment Sweet creamy vanilla coconut milky

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Human Experience:
20 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 1460 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

intraperitoneal-mouse LD50 200 mg/kg
National Technical Information Service. Vol. AD277-689

oral-guinea pig LD50 1760 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 12, Pg. 521, 1974.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
IFRA Critical Effect:
Dermal sensitization and systemic toxicity
View the IFRA Standard
View IFRA Standards Library for complete information.
Please review Amendment 49 IFRA documentation for complete information.
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%):
Category 1: Products applied to the lips
0.077 %
Category 2: Products applied to the axillae
0.023 %
Category 3: Products applied to the face/body using fingertips
0.46 %
Category 4: Products related to fine fragrance
0.43 %
Category 5: Products applied to the face and body using the hands (palms), primarily leave-on
Category 5A: Body lotion products applied to the body using the hands (palms), primarily leave-on
0.11 %
Category 5B: Face moisturizer products applied to the face using the hands (palms), primarily leave-on
0.11 %
Category 5C: Hand cream products applied to the hands using the hands (palms), primarily leave-on
0.11 %
Category 5D: Baby Creams, baby Oils and baby talc
0.03 %
Category 6: Products with oral and lip exposure
0.25 %
Category 7: Products applied to the hair with some hand contact
Category 7A: Rinse-off products applied to the hair with some hand contact
0.88 %
Category 7B: Leave-on products applied to the hair with some hand contact
0.88 %
Category 8: Products with significant anogenital exposure
0.03 %
Category 9: Products with body and hand exposure, primarily rinse off
0.84 %
Category 10: Household care products with mostly hand contact
Category 10A: Household care excluding aerosol products (excluding aerosol/spray products)
0.84 %
Category 10B: Household aerosol/spray products
3.00 %
Category 11: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate
Category 11A: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
0.03 %
Category 11B: Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
0.03 %
Category 12: Products not intended for direct skin contact, minimal or insignificant transfer to skin
No Restriction
Notes:
IFRA FLAVOR REQUIREMENTS:

Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards.

Maximised Survey-derived Daily Intakes (MSDI-EU): 1200.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 1111.00 (μg/capita/day)
Structure Class: III
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3. Update in publication number(s): 29
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 141.00000165.00000
beverages(nonalcoholic): 25.0000028.00000
beverages(alcoholic): 0.300002.00000
breakfast cereal: --
cheese: --
chewing gum: 20.00000250.00000
condiments / relishes: 10.0000015.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 95.00000104.00000
fruit ices: --
gelatins / puddings: 116.00000132.00000
granulated sugar: --
gravies: --
hard candy: 8.0000044.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 111.00000131.00000
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 80 (FGE.80) - Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008)
View page or View pdf

Flavouring Group Evaluation 80, Revision 1 (FGE.80Rev1): Consideration of alicyclic, alicyclic-fused and aromatic-fused ring lactones evaluated by JECFA (61st meeting) structurally related to a aromatic lactone evaluated by EFSA in FGE.27 (2008)
View page or View pdf

Scientific Opinion on the safety and efficacy of alicyclic and aromatic lactones (chemical group 11) when used as flavourings for all animal species
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA Substance Registry Services (TSCA):119-84-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :660
National Institute of Allergy and Infectious Diseases:Data
SCCNFP:opinion
WGK Germany:3
chroman-2-one
Chemidplus:0000119846
EPA/NOAA CAMEO:hazardous materials
RTECS:MW5775000 for cas# 119-84-6