Basic information
- Standard SMILES
CC(=O)CCC(=O)O- InChIKey
JOOXCMJARBKPKM-UHFFFAOYSA-N- Molecular formula
- C5H8O3
- Average molar mass
- 116.11 g/mol
- Monoisotopic mass
- 116.04734412
Overview
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.
Names & identifiers
- Preferred name
- Levulinic Acid
- IUPAC
- 4-oxopentanoic acid
- English name
- Levulinic acid
- Molecular formula
- C5H8O3
- Molecular weight
- 116.12
Names & synonyms
Show more names
Database identifiers
- CAS
123-76-2- PubChem CID
- 11579
- DTXSID
DTXSID8021648- ChEMBL
CHEMBL1235931- ChEBI
CHEBI:45630- UNII
- RYX5QG61EI
- EC Number
- 204-649-2
- Nikkaji
- J10.067F
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 106
Experimental & physicochemical properties
Cosmetics
Cosmetic ingredients (Levulinic Acid) -> CIR (Cosmetic Ingredient Review)
Skin conditioning
LogP
-0.49
-0.49
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
Physicochemical properties
- Melting point
- 30 · 30-33 °C (lit.)
- Boiling point
- 245 · 245-246 °C (lit.)
- Density
- 1.134 g/mL · 1.134 g/mL at 25 °C (lit.)
- vapor pressure
- 1 mm · 1 mm Hg ( 102 °C)
- refractive index
- 20 · n20/D 1.439(lit.)
- FEMA
- 2627 · 2627 | LEVULINIC ACID
- FLAVIS Number
- 8.023 · 08.023 | 4-Oxovaleric acid
- Flash point
- 280 °F · 280 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 675 g/l · 675g/l
- form
- Liquid After Melting
- pka
- 4.65 · pKa 4.65(H2O,t = 25,c=0.03-0.001) (Uncertain)
- color
- Clear yellow
- Odor
- 100 % · at 100.00 %. sweet caramel acidic acetoin buttery
- Odor Type
- caramellic
- biological source
- synthetic
- Water Solubility
- Soluble in water ( 675g/L at 20°C).
- Sensitive
- Light Sensitive
- Merck
- 14 · 14,5472
- JECFA Number
- 606 · 606
- BRN
- 506796 · 506796
- Major Application
- cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
- Cosmetics Ingredients Functions
- PERFUMINGSKIN CONDITIONING
- Cosmetic Ingredient Review (CIR)
- Levulinic acid (123-76-2)
- 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
- Surface tension
- 42.53 mN/m · 42.53mN/m at 298.15K
- Substances Added to Food (formerly EAFUS)
- LEVULINIC ACID
- FDA 21 CFR
- 172.515 · 172.515
- CAS DataBase Reference
- 123 · 123-76-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 5 QG61EI · RYX5QG61EI
- NIST Chemistry Reference
- 4 · Pentanoic acid, 4-oxo-(123-76-2)
- EPA Substance Registry System
- Levulinic acid (123-76-2)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H317-H318
- Precautionary statements
- 261 · P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
- Hazard Codes
- Xn,C
- Risk Statements
- 22 · 22-36/37/38-34-R34-R22
- Safety Statements
- 26 · 26-45-36/37/39-S45-S36/37/39-S26
- RIDADR
- 3261 · 3261
- WGK Germany
- 3 · 3
- RTECS
- 1575000 · OI1575000
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29183000 · 29183000
- Storage Class
- 13 · 13 - Non Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Sens. 1
- Toxicity
- 50 orally · LD50 orally in Rabbit: 1850 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
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.
Hazard information
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
Toxicology
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- OI1575000
- ridadr
- 3261
- hs_code
- 29183000
- Toxicity
- LD50 orally in Rabbit: 1850 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- risk_code
- 22-36/37/38-34-R34-R22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xn,C
- safety_code
- 26-45-36/37/39-S45-S36/37/39-S26
- hazard_class
- 8
- Storage Class
- 13 - Non Combustible Solids
- packing_group
- III
- Hazard statements
- H302-H317-H318
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Sens. 1
- Precautionary statements
- P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Uses & manufacturing
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]
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
Applications
UsesLevulinic acid is a biomass product and its derivatives, such as ethyl levulinate and alkyl levulinate, can be used as fuel additives. levulinic acid is used for calcium levulinate in pharmaceuticals, as esters in solvents and plasticizers, and for making valerolactone. As its uses expand, it will probably be made from cellulosic wastes. Mesitonic acid, a homolog of levulinic acid is obtained by boiing mesityl oxide with KCN. Hydrogenation of levulinic acid can produce other useful chemicals. Valeric-g-lactone, which is an effective solvent with extensive uses, can be obtained in very high yields. This compound may be hydrogenated to 1,4-pentandiol, which upon dehydration yields 1,3-pentadine (piperylene). Piperylene is known to polymerize to a rubbery mass and is therefore a source of synthetic rubber (Ghorpade and Hanna 1997). Levulinic acid is a precursor for the synthesis of useful intermediates such as γ-valerolactone, ethyl levulinate, pentanoic acid and 2-methyl-tetrahydrofuran. Derivatization and esterification of levulinic acid results in potential biofuels. It can also be used in: The preparation of catalytic composite to synthesize 5-hydroxymethylfurfural and furfural. The synthesis of a commercial fragrance, fraistone. The synthesis of pyrrolidone derivatives via reductive amination. The total synthesis of mycobacterial arabinogalactan.
DescriptionLevulinic 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.
UsesLevulinic 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).
UsesReplenisher (calcium).
UsesLevulinic acid is a precursor for the synthesis of useful intermediates such as γ-valerolactone, ethyl levulinate, pentanoic acid and 2-methyl-tetrahydrofuran. Derivatization and esterification of levulinic acid results in potential biofuels.It can also be used in:The preparation of catalytic composite to synthesize 5-hydroxymethylfurfural and furfural.The synthesis of a commercial fragrance, fraistone.The synthesis of pyrrolidone derivatives via reductive amination.The total synthesis of mycobacterial arabinogalactan.
General DescriptionLevulinic acid, an organic acid, is mainly used as a cigarette additive.
Preparation methods
PreparationThe residue during the manufacturing of furfural with cotton seed shell or corncob sugar (furfural residue) or waste taro residue, through pressured hydrolysis with dilute acid, can be used to produce levulinic acid. The furfural residue was added to 10% dilute hydrochloric acid, the solidified solution was 1: 1.75, mixed and put into the hydrolysis pot, steamed at a pressure of 0.2MPa for 8-10 h. The diluted solution is then filtered and concentrated to a concentration of about 50%. It is further subject to vacuum distillation for collecting the fraction above 130 ℃ (2.67kPa) to obtain the finished product. Raw material consumption quota: potato tacar 7,000 kg/t, hydrochloric acid (fold 100%) 1800kg/t. Another method is manufacturing through the rearrangement and hydrolysis of sugar alcohol. 4% hydrochloric acid solution was added to the reaction pot, stir and heat to 97-100 ℃, slowly add the mixture of furfuryl alcohol, ethanol and water. After addition, stir 30 min. The filtrate was concentrated at 80 ° C (21.3 kPa) under reduced pressure to give crude levulinic acid. Then apply vacuum distillation, collect the fraction of 160-170 ° C (2.67kPa), and then re-distill once, to obtain the refined levulinic acid with the yield of about 75%.
PreparationBy action of more or less concentrated HCl on sucrose, glucose or fructose; hence, its reported presence in caramels.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: 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 a straight-chain saturated fatty acid and an oxopentanoic acid. It is a conjugate acid of a 4-oxopentanoate.
Related reactions
Linked notes
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