2-Oxobutanoic Acid
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Basic information
- CAS
600-18-0- Standard SMILES
CCC(=O)C(=O)O- InChIKey
TYEYBOSBBBHJIV-UHFFFAOYSA-N- Molecular formula
- C4H6O3
- Average molar mass
- 102.09 g/mol
- Monoisotopic mass
- 102.03169405
Overview
2-oxobutanoic acid is a 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid. It is a short-chain fatty acid and a 2-oxo monocarboxylic acid. It is functionally related to a butyric acid. It is a conjugate acid of a 2-oxobutanoate.
Names & identifiers
- Preferred name
- 2-Oxobutanoic Acid
- IUPAC
- 2-oxobutanoic acid
- English name
- 2-Oxobutyric acid
- Molecular formula
- C4H6O3
- Molecular weight
- 102.09
Names & synonyms
2-oxobutanoic acid600-18-02-ketobutyric acid2-oxobutyric acidalpha-ketobutyric acidBUTANOIC ACID, 2-OXO-3-Methylpyruvic acidKetobutyrate2-oxobutyrate2-Ketobutanoic acidButyric acid, 2-oxo-alpha-Oxo-n-butyric acid
Show more names
FEMA 3723Oxobutyrate2-KETOBUTYRATEα-Ketobutyric AcidKetobutyric aci
alpha-oxobutyric acidalpha-ketobutyratealpha-OxobutyrateFEMA No. 3723B92RB6HY1ANSC-60533DTXSID9060524CHEBI:30831
Database identifiers
- CAS
600-18-0- PubChem CID
- 58
- DTXSID
DTXSID9060524- ChEMBL
CHEMBL171246- ChEBI
CHEBI:30831- UNII
- B92RB6HY1A
- EC Number
- 209-986-9
- Nikkaji
- J2.726J
Properties
Computed structural propertiesFilling in
- XLogP
- 0.1
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 95.1
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Oxo fatty acids [FA0106]
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.200 (d20/4)
Flavoring AgentsEU Flavoring substances
Solubility
119 mg/mL
soluble in water and alcohol
(in ethanol)
Boiling Point80-82 °C (16 mm Hg)
Melting Point33 °C
Physical Description
Colorless hygroscopic paste; mp = 32-34 deg C; [Acros Organics MSDS]
Solid
Physicochemical properties
- Melting point
- 30 · 30-34 °C(lit.)
- Boiling point
- 84 °C20 · 84 °C20 mm Hg(lit.)
- Density
- 1.2 · 1.2000
- refractive index
- 1.3972 · 1.3972 (estimate)
- FEMA
- 3723 · 3723 | 2-OXOBUTYRIC ACID
- FLAVIS Number
- 8.066 · 08.066 | 2-Oxobutyric acid
- Flash point
- 179 °F · 179 °F
- storage temp.
- 2 °C · Store at +2°C to +8°C.
- solubility
- 2 O: · H2O: soluble0.1g/mL, clear
- pka
- 2.5 · 2.5(at 25℃)
- form
- liquid
- Specific Gravity
- 1.3972 · 1.3972 (20/4℃)
- color
- White to Almost white
- Odor
- 1 % · at 1.00 % in propylene glycol. sweet brown caramel creamy lactonic
- PH
- 3.11 · 3.11(1 mM solution);2.38(10 mM solution);1.79(100 mM solution);
- Odor Type
- caramellic
- biological source
- synthetic
- JECFA Number
- 589 · 589
- BRN
- 1700514 · 1700514
- Major Application
- cleaning productscosmeticsfood and beveragespersonal care
- InChI
- 1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
- InChIKey
- TYEYBOSBBBHJIV-UHFFFAOYSA-N
- SMILES
- CCC(C(O)=O)=O
- LogP
- -0.75 · -0.75
- CAS DataBase Reference
- 600 · 600-18-0(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (99.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1442 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Butanoic acid, 2-oxo-
2-Oxobutyric 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 SummarySafe when used as a flavoring agent in food; [JECFA] An irritant; May cause CNS depression; [Acros Organics MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (99.8%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- 1759
- hs_code
- 29183000
- risk_code
- 36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- safety_code
- 26-36/37/39-36
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H314
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1B
- Precautionary statements
- P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationButanoic acid, 2-oxo-: ACTIVE
Applications
OccurrenceReported found in beer and black tea.
UsesA substrate for the determination of lactate dehydrogenase isoenzymes.This compound is suitable for lactate dehydrogenase (LDH) related research.
Uses2-Oxobutyric acid (α-ketobutyric acid) may be used as an analytical reference standard for the determination of the analyte in K562 cells by high-performance liquid chromatography with fluorescence detection and in drinking water at low microgram per liter concentrations by ion chromatography technique.
General Description2-Oxobutyric acid is mainly found in the hydrolysates of proteins, reportedly being formed by the degradation of threonine.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid.
Related reactions
76 records
Compound notes
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