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Category:flavoring agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Appearance: | pale yellow to yellow clear liquid (est) |
| Assay: | 95.00 to 100.00
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| Water Content: | <0.2 % |
| Food Chemicals Codex Listed: | No |
| Specific Gravity: | 1.10100 to 1.10700 @ 25.00 °C.
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| Pounds per Gallon - (est).: | 9.161 to 9.211
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| Refractive Index: | 1.45100 to 1.45700 @ 20.00 °C.
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| Melting Point: | -13.00 to -11.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 219.00 °C. @ 760.00 mm Hg
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| Vapor Pressure: | 0.129000 mmHg @ 25.00 °C. (est) |
| Flash Point: | 233.00 °F. TCC ( 111.67 °C. )
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| logP (o/w): | -0.350 |
| Shelf Life: | 12.00 month(s) or longer if stored properly. |
| Storage: | refrigerate in tightly sealed containers. |
| Soluble in: |
| | alcohol | | | water, 2.326e+005 mg/L @ 25 °C (est) |
| Insoluble in: |
| | water |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
| European information : |
| Most important hazard(s): | | Xi - Irritant |
R 41 - Risk of serious damage to eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
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| |
| Hazards identification |
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| 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 | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
oral-rat LD50 > 2000 mg/kg
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | flavoring agents |
| Recommendation for delta-valerolactone usage levels up to: | | | not for fragrance use.
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| |
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.012 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 3900 (μg/person/day) |
| Threshold of Concern: | 1800 (μg/person/day) |
| Structure Class: | I |
| |
| Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). |
| Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. |
| | average usage mg/kg | maximum usage mg/kg |
| Dairy products, excluding products of category 02.0 (01.0): | 7.00000 | 35.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 5.00000 | 25.00000 |
| Edible ices, including sherbet and sorbet (03.0): | 10.00000 | 50.00000 |
| Processed fruit (04.1): | 7.00000 | 35.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - |
| Confectionery (05.0): | 10.00000 | 50.00000 |
| Chewing gum (05.3): | - | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 5.00000 | 25.00000 |
| Bakery wares (07.0): | 10.00000 | 50.00000 |
| Meat and meat products, including poultry and game (08.0): | 2.00000 | 10.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 2.00000 | 10.00000 |
| Eggs and egg products (10.0): | - | - |
| Sweeteners, including honey (11.0): | - | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 5.00000 | 25.00000 |
| Foodstuffs intended for particular nutritional uses (13.0): | 10.00000 | 50.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 5.00000 | 25.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 10.00000 | 50.00000 |
| Ready-to-eat savouries (15.0): | 20.00000 | 100.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 5.00000 | 25.00000 |
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
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European Food Safety Authority (EFSA) reference(s):
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Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf
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Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf
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Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
View page or View pdf
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Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones evaluated by EFSA in FGE.10Rev1 (2009)
View page or View pdf
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Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf
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Scientific Opinion on Flavouring Group Evaluation 10, Revision 3 (FGE.10Rev3): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf
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| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):542-28-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :10953 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| tetrahydro-2H-pyran-2-one |
| Chemidplus:0000542289 |
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | oxan-2-one | | | pentano-1,5-lactone | | | pentanoic acid, 5-hydroxy-, d-lactone | | d- | pentanolactone | | 2H- | pyran-2-one, tetrahydro- | | | tetrahydro-2-pyranone | | | tetrahydro-2H-pyran-2-one | | 3H-4,5,6- | trihydropyran-2-one | | | valeric acid, d-hydroxy-, d-lactone | | d- | valerolactone | | delta- | valeryl lactone | | d- | valeryllactone |
Articles:
| Google Patents:Process for preparing delta-valerolactone in the gas phase |
| PubMed:[Studies on chemical constituents of Ranunculus ternatus]. |
| PubMed:High activity of an indium alkoxide complex toward ring opening polymerization of cyclic esters. |
| PubMed:Star/linear polymer topology transformation facilitated by mechanical linking of polymer chains. |
| PubMed:N-Heterocyclic Carbene-Catalyzed Ring Opening Polymerization of ε-Caprolactone with and without Alcohol Initiators: Insights from Theory and Experiment. |
| PubMed:Role of hydrophilicity and length of diblock arms for determining star polymer physical properties. |
| PubMed:In situ gelling polyvalerolactone-based thermosensitive hydrogel for sustained drug delivery. |
| PubMed:Scalable production of mechanically tunable block polymers from sugar. |
| PubMed:Tensile behavior and dynamic mechanical analysis of novel poly(lactide/δ-valerolactone) statistical copolymers. |
| PubMed:Experimental and computational studies on the mechanism of zwitterionic ring-opening polymerization of δ-valerolactone with N-heterocyclic carbenes. |
| PubMed:Folic acid conjugated δ-valerolactone-poly(ethylene glycol) based triblock copolymer as a promising carrier for targeted doxorubicin delivery. |
| PubMed:Abnormal N-heterocyclic carbene main group organometallic chemistry: a debut to the homogeneous catalysis. |
| PubMed:New mechanism for the ring-opening polymerization of lactones? Uranyl aryloxide-induced intermolecular catalysis. |
| PubMed:Mechanisms of lactone hydrolysis in neutral and alkaline conditions. |
| PubMed:Mechanisms of lactone hydrolysis in acidic conditions. |
| PubMed:Photoswitchable NHC-promoted ring-opening polymerizations. |
| PubMed:Drug-Initiated, Controlled Ring-Opening Polymerization for the Synthesis of Polymer-Drug Conjugates. |
| PubMed:Conformational analysis of δ-lactones by DFT calculations: the parent compound and its monomethyl and selected dimethyl derivatives. |
| PubMed:Triarylsulfonium hexafluorophosphate salts as photoactivated acidic catalysts for ring-opening polymerisation. |
| PubMed:Direct catalytic asymmetric addition of allylic cyanides to aldehydes for expeditious access to enantioenriched unsaturated δ-valerolactones. |
| PubMed:Biocatalytic synthesis of poly(δ-valerolactone) using a thermophilic esterase from archaeoglobus fulgidus as catalyst. |
| PubMed:Palladium-catalyzed synthesis of 4-oxaspiro[2.4]heptanes via central attack of oxygen nucleophiles to π-allylpalladium intermediates. |
| PubMed:Nanoaggregates of biodegradable amphiphilic random polycations for delivering water-insoluble drugs. |
| PubMed:Novel biodegradable, biomimetic and functionalised polymer scaffolds to prevent expansion of post-infarct left ventricular remodelling. |
| PubMed:Introduction of abnormal N-heterocyclic carbene as an efficient organocatalyst: ring opening polymerization of cyclic esters. |
| PubMed:Evaluation of triblock copolymeric micelles of δ- valerolactone and poly (ethylene glycol) as a competent vector for doxorubicin delivery against cancer. |
| PubMed:Pseudomonas putida esterase contains a GGG(A)X-motif confering activity for the kinetic resolution of tertiary alcohols. |
| PubMed:Biodegradable polyurethane ureas with variable polyester or polycarbonate soft segments: effects of crystallinity, molecular weight, and composition on mechanical properties. |
| PubMed:Artificial molecular clamp: a novel device for synthetic polymerases. |
| PubMed:Ring-opening polymerization of cyclic esters and trimethylene carbonate catalyzed by aluminum half-salen complexes. |
| PubMed:Synthesis, analytical features, and biological relevance of 5-(3',4'-dihydroxyphenyl)-γ-valerolactone, a microbial metabolite derived from the catabolism of dietary flavan-3-ols. |
| PubMed:Ring openings of lactone and ring contractions of lactide by frustrated Lewis pairs. |
| PubMed:Stereoselective rearrangement of guaianolides to tricyclic δ-valerolactones. |
| PubMed:Molecular and electronic structure of δ-valerothiolactone. |
| PubMed:Preparation of enzymatically recyclable hydrogels through the formation of inclusion complexes of amylose in a vine-twining polymerization. |
| PubMed:Palladium-catalyzed decarboxylative [4 + 3] cyclization of gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanes. |
| PubMed:Geometry dependence of the ring-opening E2 reaction in lactones. |
| PubMed:Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins. |
| PubMed:Thermodynamic control of the polymerizability of five-, six-, and seven-membered lactones. |
| PubMed:Switching of polymerization activity of cinnamoyl-alpha-cyclodextrin. |
| PubMed:Nanospheres with polymerization ability coated by polyrotaxane. |
| PubMed:Diastereoselective preparation of substituted delta-valerolactones. synthesis of (3R,4S)- and (3R,4R)-simplactones. |
| PubMed:Stereoselective synthesis of nipecotic acid derivatives via palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with imines. |
| PubMed:[Studies on chemical constituents of Ranunculus ternatus]. |
| PubMed:Plasmon microscopy and imaging ellipsometry of Artrobacter oxydans attached on polymer films. |
| PubMed:Approach to formation of multifunctional polyester particles in controlled nanoscopic dimensions. |
| PubMed:Why delta-valerolactone polymerizes and gamma-butyrolactone does not. |
| PubMed:An artificial molecular chaperone: poly-pseudo-rotaxane with an extensible axle. |
| PubMed:Enzymatic synthesis of poly(hydroxyalkanoates) in ionic liquids. |
| PubMed:X-ray investigations of bicyclic alpha-methylene-delta-valerolactones. V. (4aS,7R,8aR)-7-isopropenyl-4a-methyl-3-methyleneperhydrochromen-2-one. |
| PubMed:Thermal degradation of environmentally degradable poly(hydroxyalkanoic acid)s. |
| PubMed:Synthesis of trimethoxy- or triethoxysilane-endcapped polylactones via a bismuth(III)hexanoate-catalyzed one-pot-procedure. |
| PubMed:The effect of carbonyl substitution on the strain energy of small ring compounds and their six-member ring reference compounds. |
| PubMed:Epidermal growth factor-conjugated poly(ethylene glycol)-block- poly(delta-valerolactone) copolymer micelles for targeted delivery of chemotherapeutics. |
| PubMed:Degradation and controlled release behavior of epsilon-caprolactone copolymers in biodegradable antifouling coatings. |
| PubMed:Methoxy poly(ethylene glycol)-block-poly(delta-valerolactone) copolymer micelles for formulation of hydrophobic drugs. |
| PubMed:Characterization of pegylated copolymeric micelles and in vivo pharmacokinetics and biodistribution studies. |
| PubMed:New biodegradable amphiphilic block copolymers of epsilon-caprolactone and delta-valerolactone catalyzed by novel aluminum metal complexes. II. Micellization and solution to gel transition. |
| PubMed:High affinity, stability, and lactonase activity of serum paraoxonase PON1 anchored on HDL with ApoA-I. |
| PubMed:Comparison of two pegylated copolymeric micelles and their potential as drug carriers. |
| PubMed:A kinetic approach to the alkylating potential of carcinogenic lactones. |
| PubMed:Synthesis and characterization of six-arm star poly(delta-valerolactone)-block-methoxy poly(ethylene glycol) copolymers. |
| PubMed:Antinociceptive effects of some synthetic delta-valerolactones. |
| PubMed:X-ray investigations of bicyclic alpha-methylene-delta-valerolactones. III. trans-(4aR,8aR)-4a-Methoxy-3-methyleneperhydrochromen-2-one. |
| PubMed:PEG- and peptide-grafted aliphatic polyesters by click chemistry. |
| PubMed:A novel formal total synthesis of cephalotaxine. |
| PubMed:Reactivity of lactones and GHB formation. |
| PubMed:A novel approach to biodegradable block copolymers of epsilon-caprolactone and delta-valerolactone catalyzed by new aluminum metal complexes. |
| PubMed:New synthetic approach to cyclopenta-fused heterocycles based upon a mild nazarov reaction. 2. Further studies on the torquoselectivity. |
| PubMed:API-mass spectrometry of polyketides. I. A study on the fragmentation of triketide lactones. |
| PubMed:Highly diastereoselective hydrogenations leading to beta-hydroxy delta-lactones in hydroxy-protected form. A modified view of delta-lactone conformations. |
| PubMed:Recent developments in sonochemical polymerisation. |
| PubMed:Correlation between structure of the lactones and substrate specificity in enzyme-catalyzed polymerization for the synthesis of polyesters. |
| PubMed:Ring-opening iodo- and bromosilation of lactones for the formation of silyl haloalkanoates. |
| PubMed:Conformation-dependent reaction thermochemistry: study of lactones and lactone enolates in the gas phase. |
| PubMed:Ring-opening polymerization of lactones in the presence of hydroxyapatite. |
| PubMed:In vitro degradation and dissolution behaviours of microspheres prepared by three low molecular weight polyesters. |
| PubMed:Unknown bisethylisooctanollactone isomers in industrial waste water. Isolation, identification and occurrence in surface water. |
| PubMed:Development of new dihydropyran linker for solid-phase reaction. |
| PubMed:Comparison of thermal characteristics and degradation properties of epsilon-caprolactone copolymers. |
| PubMed:Screening, nucleotide sequence, and biochemical characterization of an esterase from Pseudomonas fluorescens with high activity towards lactones. |
| PubMed:An evaluation of a new lactic acid polymer drug delivery system: a preliminary report. |
| PubMed:Therapeutic gamma-hydroxybutyric acid monitoring in plasma and urine by gas chromatography-mass spectrometry. |
| PubMed: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. |
| PubMed:Evaluation of new pasty-type implantable devices consisting of poly(epsilon-caprolactone/delta-valerolactone) and Estracyt or estramustine. |
| PubMed:A new biodegradable copolymer of glycolic acid and lactones with relatively low molecular weight prepared by direct copolycondensation in the absence of catalysts. |
| PubMed:Derivatives of ethynylestradiol with oxygenated 17 alpha-alkyl side chain: synthesis and biological activity. |
| PubMed:Poly(hydroxy acids) in drug delivery. |
| PubMed:Aliphatic polyesters II. The degradation of poly (DL-lactide), poly (epsilon-caprolactone), and their copolymers in vivo. |
| PubMed:Stimulation of hydroxymethylglutaryl-CoA reductase activity after a single dose of the porphyrogenic chemical, allylisopropylacetamide. |
| PubMed:Model studies directed toward the total synthesis of vernolepin. III. Synthesis of the alpha-methylene-delta-valerolactone ab ring model. |
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3D/inchi