4-oxopentanoic acid

• ChemBase ID: 1990
• Molecular Formular: C5H8O3
• Molecular Mass: 116.11522
• Monoisotopic Mass: 116.04734412
• SMILES: CC(=O)CCC(=O)O
• Canonical SMILES: CC(=O)CCC(=O)O
• InChI: InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
• InChIKey: JOOXCMJARBKPKM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-oxopentanoic acid
• IUPAC Traditional name: levulinic acid
• Synonyms: 4-Oxopentanoic acid; 4-Oxovaleric acid; Levulinic acid; 4-Ketopentanoic acid; Laevulinic Acid; Levulinic acid; Laevulinic acid; β-Acetylpropionic acid; 3-Acetopropionic acid; γ-ketovaleric acid; 4-Oxopentanoic acid; β-Ketovaleric acid; LEVULINIC ACID; 4-氧代戊酸; 4-酮正戊酸; 乙酰丙酸

Database IDs

• CAS Number: 123-76-2
• EC Number: 204-649-2
• MDL Number: MFCD00002796
• Beilstein Number: 506796
• Merck Index: 145472
• PubChem SID: 24896298; 160965445; 24882128; 24901210; 46504792
• PubChem CID: 11579
• CHEBI ID: 45630
• CHEMBL: 1235931
• Chemspider ID: 11091
• DrugBank ID: DB02239
• FEMA ID: 2627
• Unique Ingredient Identifier: RYX5QG61EI
• Wikipedia Title: Levulinic_acid
• Council of Europe Number: 23
• Flavis Number: 8.023

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.321649
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.2731656
• LogD (pH = 7.4): -3.0159836
• Log P: -0.06885745
• Molar Refractivity: 27.0881 cm^3
• Polarizability: 10.62324 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.14
• LOG S: 0.08
• Solubility (Water): 1.39e+02 g/l

PROPERTIES

Physical Property

• Melting Point: 26-31°C; 30-33 °C(lit.); 30-33°C; 33–35 °C
• Boiling Point: 245°C; 245-246 °C(lit.); 245–246 °C; 245-246°C
• Flash Point: 137°C; 137°C(278°F); 208.4 °F; 98 °C
• Density: 1.13 g/ml; 1.134; 1.134 g/mL at 25 °C(lit.); 1.1447 g/cm^3
• Refractive Index: 1.4415
• Vapor Pressure: 1 mm Hg @ 102°C; 1 mmHg ( 102 °C)
• Hydrophobicity(logP): -0.49 [HANSCH,C ET AL. (1995)]
• Organoleptic: wine-like

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT; Light Sensitive
• RTECS: OI1575000
• European Hazard Symbols: Corrosive (C); X; Harmful (Xn)
• UN Number: 1760; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: II; III
• Australian Hazchem: 2X
• Risk Statements: 22-34; 22-36/37/38; R:22-34
• Safety Statements: 26; 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• EU Classification: C9
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false; 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H314-H318-H302
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FDA 21 CFR (172.515)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: >98%; ≥97%; ≥97.0% (GC); 95+%; 97%; 98%
• Grade: FG; Halal; Kosher; NI; purum
• Impurities: ~1% water
• Linear Formula: CH3COCH2CH2COOH

DETAILS

MP Biomedicals - 02155229

(4-Oxopentanoic acid; γ-Ketovaleric acid) Free Acid Purity: >98% White to pale yellow crystals

DrugBank - DB02239

• Drug Groups: experimental
• External Links: Wikipedia

Sigma Aldrich - L2009

Packaging
1 kg in poly bottle
50, 250 g in poly bottle

Sigma Aldrich - W262706

Packaging
1 kg in glass bottle
5kg, 10kg packaged in closed-head poly drums; sample packaged in glass bottles; 1kg packaged in poly bottles
1 sample in glass bottle
5, 10, 25 kg in poly drum

Sigma Aldrich - 61380

Caution
readily supercools; white to pale yellow crystals when solid
Other Notes
Hydroxyl protecting reagent, used in carbohydrate chemistry1,2

REFERENCES

• Alcohols and phenols can be protected as levulinate (Lev) esters. Ester formation has been brought about, e.g. by reaction with an alcohol in the presence of DCC and DMAP: Tetrahedron Lett., 4875 (1976); 23, 2615 (1982). The same references describe facile, selective cleavage by the use of hydrazine hydrate in pyridine/acetic acid. For use of 2-Chloro-1-methylpyridinium iodide, A12820, in the formation of Lev esters, see: Tetrahedron Lett., 21, 381 (1980). Alternative cleavage methods include: borohydride in water: J. Am. Chem. Soc., 97, 1614 (1975); MeMgI: benzoate esters unaffected: J. Chem. Soc., Chem. Commun., 681 (1992); sodium sulfite/ bisulfite under neutral conditions, effective for Lev esters of nucleosides, carbohydrates and steroids: Chem. Lett., 585 (1988). Lev esters have also been prepared using 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline, A13724: Tetrahedon Lett., 23, 2615 (1982).