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4-Oxovaleriansure

Levulinic Acid

HCID 11579
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Grundinformationen

CAS
123-76-2
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 StruktureigenschaftenWird ergänzt

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 · 2 Einträge

Cosmetic ingredients (Levulinic Acid) -> CIR (Cosmetic Ingredient Review)

Skin conditioning

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Levulinic acid) -> IFRA transparency List
LogP · 2 Einträge

-0.49

-0.49

Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.136-1.147 (20 °C)
Flavoring Agents

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 5 Einträge

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

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 · 3 Einträge

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 · 6 Einträge

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 · 2 Einträge

Plastics Material and Resin Manufacturing

Pentanoic acid, 4-oxo-: ACTIVE

Zugehörige Reaktionen

130
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 1516
HRID 1516als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 1585
HRID 1585als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2090
HRID 2090als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2131
HRID 2131als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2189
HRID 2189als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 10756
HRID 10756als Eduktuspto-grants-2006_08
Reaktionsgleichung von HRID 25892
HRID 25892als Eduktuspto-grants-1979_04
Reaktionsgleichung von HRID 65892
HRID 65892als Eduktuspto-grants-1978_12
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EU Flavoring substances
Solubility · 2 Einträge

soluble in water, alcohol, and oil

1 mL in 1 mL 95% alcohol (in ethanol)

Boiling Point · 2 Einträge

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)
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
Anwendungen · 3 Einträge

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

UraldehydeSugar alcoholFurfurylalkoholDilute hydrochloric acidStrke

Nachgelagerte Produkte

IndometacinDL-2-Methylglutaminsure4,4-Bis(4-hydroxyphenyl)valeriansure(2,4-DIMETHYLQUINOLIN-3-YL)ACETIC ACID HYDROCHLORIDEγ-Valerolacton(6-CHLORO-2-METHYL-4-PHENYLQUINOLIN-3-YL)ACETIC ACIDN-Butyl-4-oxopentanoat(2-METHYL-4-PHENYLQUINOLIN-3-YL)ACETIC ACID HYDROCHLORIDE6-Methylpyridazin-3-aminAmeisensureBernsteinsureEthyl-4-oxovalerat4,4'-Azobis[4-cyanvalerian]sure5-hydroxy-4-oxopentanoic acidPentylvalerat2-METHYLINDOLE-3-ACETIC ACID2,3-Dihydro-4-methyl-2-thioxothiazol-5-essigsureMethyl-5-amino-4-oxovalerathydrochloridPentan-1,4-diol