Grundinformationen
- Standard-SMILES
CC(=O)CCC(=O)O- InChIKey
JOOXCMJARBKPKM-UHFFFAOYSA-N- Summenformel
- C5H8O3
- Durchschnittliche Molmasse
- 116,11 g/mol
- Monoisotopische Masse
- 116,04734412
Überblick
4-oxopentanoic acid is an oxopentanoic acid with the oxo group in the 4-position. It has a role as a plant metabolite. It is an oxopentanoic acid and a straight-chain saturated fatty acid. It is a conjugate acid of a 4-oxopentanoate.
Namen und Bezeichner
- Bevorzugter Name
- Levulinic Acid
- IUPAC
- 4-oxopentanoic acid
- Lokaler Name
- 4-Oxovaleriansure
- Englischer Name
- Levulinic acid
- Summenformel
- C5H8O3
- Molmasse
- 116.12
Namen und Synonyme
LEVULINIC ACID4-Oxopentanoic acid123-76-2Laevulinic acidPentanoic acid, 4-oxo-4-Oxovaleric acidLevulic acid4-Ketovaleric acidgamma-Ketovaleric acidLEVAAcetopropionic acidLevulinsaeure
Weitere Namen anzeigen
LAlevulinicAcetylpropionic acidFEMA 26272-KETOVALERIC ACID
Laevulic acidbeta-Acetylpropionic acidAcidum laevulinicumFEMA No. 2627DTXSID8021648RYX5QG61EINSC-3716DTXCID701648
Datenbank-Bezeichner
- CAS
123-76-2- PubChem CID
- 11579
- DTXSID
DTXSID8021648- ChEMBL
CHEMBL1235931- ChEBI
CHEBI:45630- UNII
- RYX5QG61EI
- EC Number
- 204-649-2
- Nikkaji
- J10.067F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,5
- Polarare Oberfläche (TPSA)
- 54,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 106
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Oxo fatty acids [FA0106]
Cosmetics
Cosmetic ingredients (Levulinic Acid) -> CIR (Cosmetic Ingredient Review)
Skin conditioning
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Levulinic acid) -> IFRA transparency List
LogP
-0.49
-0.49
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.136-1.147 (20 °C)
Flavoring AgentsEU Flavoring substances
Solubility
soluble in water, alcohol, and oil
1 mL in 1 mL 95% alcohol (in ethanol)
Boiling Point
245.00 to 246.00 °C. @ 760.00 mm Hg
245 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 30 · 30-33 °C (lit.)
- Siedepunkt
- 245 · 245-246 °C (lit.)
- Dichte
- 1.134 g/mL · 1.134 g/mL at 25 °C (lit.)
- Dampfdruck
- 1 mm · 1 mm Hg ( 102 °C)
- Brechungsindex
- 20 · n20/D 1.439(lit.)
- FEMA
- 2627 · 2627 | LEVULINIC ACID
- Flammpunkt
- 280 °F · 280 °F
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 675 g/l · 675g/l
- Aggregatzustand
- Liquid After Melting
- pka
- 4.65 · pKa 4.65(H2O,t = 25,c=0.03-0.001) (Uncertain)
- Farbe
- Clear yellow
- Geruch (Odor)
- 100 % · at 100.00 %. sweet caramel acidic acetoin buttery
- Geruchsart
- caramellic
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- Soluble in water ( 675g/L at 20°C).
- Merck
- 14 · 14,5472
- JECFA Number
- 606 · 606
- BRN
- 506796 · 506796
- Major Application
- cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
- Kosmetik-Inhaltsstoffe Funktionen
- PERFUMINGSKIN CONDITIONING
- InChI
- 1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
- InChIKey
- JOOXCMJARBKPKM-UHFFFAOYSA-N
- SMILES
- CC(=O)CCC(O)=O
- LogP
- -0.498 · -0.498
- Oberflächenspannung
- 42.53 mN/m · 42.53mN/m at 298.15K
- CAS Datenbank
- 123 · 123-76-2(CAS DataBase Reference)
- NIST chemische Informationen
- 4 · Pentanoic acid, 4-oxo-(123-76-2)
- EPA chemische Informationen
- Levulinic acid (123-76-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H302 (99.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P305+P354+P338, P317, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1892 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: Pentanoic acid, 4-oxo-
Regulation (EC) No 1831/2003 (amended)
Pentanoic acid, 4-oxo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pentanoic acid, 4-oxo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 06-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17335
Levulinic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryA moderate skin irritant; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; Harmful by ingestion; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (99.9%)
Toxikologische Informationen
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- 3261
- hs_code
- 29183000
- RTECS-Nr.
- OI1575000
- risk_code
- 22-36/37/38-34-R34-R22
- Toxizität
- LD50 orally in Rabbit: 1850 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- hazard_code
- Xn,C
- safety_code
- 26-45-36/37/39-S45-S36/37/39-S26
- hazard_class
- 8
- packing_group
- III
- Speicherklasse
- 13 - Non Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Sens. 1
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Tissue LocationsNeuron
Cellular LocationsCytoplasm
Verwendung und Herstellung
Uses
CIR ingredient: Levulinic Acid
Used to make nylon, synthetic rubber, plastic, and medicinals; [Merck Index] Used as a flavoring agent; [FDA] Used to flavor animal feeds; [ExPub: EFSA - FEEDAP]
Farming (Feed Additives) [Category: Industry]
U.S. Production2023: 50,000 - <250,000 lb
Consumer UsesIntermediate
Industry UsesLaboratory chemicals
Household ProductsInformation on 1 consumer products that contain Levulinic Acid in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Plastics Material and Resin Manufacturing
Pentanoic acid, 4-oxo-: ACTIVE
Anwendungen
BeschreibungLevulinic acid has a tart, whiskey taste. It may be synthesized by the action of more or less concentrated HCL on sucrose, glucose, or fructose; hence, its reported presence in caramels.
OccurrenceReported found in papaya, wheat bread, rice, sake and Chinese quince.
VerwendenLevulinic acid may be used as an analytical reference standard for the quantification of the analyte in the following:Soy sauce using liquid chromatography coupled to mass spectrometry (LC–MS).Liquid food samples using gas chromatography with flame ionization detection (GC-FID).
Darstellung
synthetischeBy action of more or less concentrated HCl on sucrose, glucose or fructose; hence, its reported presence in caramels.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
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