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123-76-2

Basic Information
CAS No.: 123-76-2
Name: Levulinic acid
Article Data: 511
Molecular Structure:
Molecular Structure of 123-76-2 (Levulinic acid)
Formula: C5H8O3
Molecular Weight: 116.117
Synonyms: Propionic acid, 3-acetyl-;4-Ketovaleric acid;Valeric acid, 4-oxo-;Pentanoic acid, 4-oxo-;Pentanoic acid,4-oxo-;4-Oxopentanoic acid;LEVA;Levulinicacid;Usaf cz-1;Acetopropionic acid;4-Oxovaleric acid;.gamma.-Ketovaleric acid;3-Acetylpropionic acid;4-oxopentanoate;
EINECS: 204-649-2
Density: 1.129 g/cm3
Melting Point: 30-33 °C(lit.)
Boiling Point: 242.9 °C at 760 mmHg
Flash Point: 115 °C
Solubility: Soluble in water ( 675g/L at 20°C).
Appearance: clear yellowish liquid after melting
Hazard Symbols: HarmfulXn,CorrosiveC
Risk Codes: 22-36/37/38-34
Safety: 26-45-36/37/39
Transport Information: 3261
PSA: 54.37000
LogP: 0.44020
Synthetic route
6089-09-4

4-pentynoic acid

123-76-2

levulinic acid

Conditions
ConditionsYield
In water at 90℃; for 7h; Reagent/catalyst; Temperature;100%
With [RhCl2(p-cymene)]2; water at 20℃; for 12h;92%
gold(I) chloride In acetonitrile at 20℃;77%
626-96-0

4-oxopentanal

123-76-2

levulinic acid

Conditions
ConditionsYield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;95%
With silver(l) oxide
67-47-0

5-hydroxymethyl-2-furfuraldehyde

57-48-7

D-Fructose

123-76-2

levulinic acid

Conditions
ConditionsYield
With sulfuric acid; water at 90℃; for 1h; Concentration;96%
57-48-7

D-Fructose

123-76-2

levulinic acid

Conditions
ConditionsYield
With sulfuric acid In water at 100 - 120℃; for 3h; Temperature; Concentration; Flow reactor;94.83%
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate In water at 170℃; for 5h; Autoclave;76.7%
With Amberlyst-15 In 1,4-dioxane; water at 150℃; for 3h; Reagent/catalyst; Solvent; Time;71%
10008-73-8

5-methylenedihydrofuran-2-one

123-76-2

levulinic acid

Conditions
ConditionsYield
With Lewalit S 100 G1 In benzene for 6h; Ambient temperature;94%
With dichlorobis(dimethyl sulfoxide)platinum(II) In water at 37℃; for 24h;
108-29-2

5-methyl-dihydro-furan-2-one

123-76-2

levulinic acid

Conditions
ConditionsYield
In potassium hydroxide at 30℃; electrolysis: nickel hydroxide electrode, 1.5-1.6 V;94%
With tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃;78%
67-47-0

5-hydroxymethyl-2-furfuraldehyde

123-76-2

levulinic acid

Conditions
ConditionsYield
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate In water at 170℃; for 5h; Autoclave;93.4%
sulfuric acid In 2-sec-butylphenol; water at 150℃; for 1h; Product distribution / selectivity;90%
With water at 155 - 160℃; im Autoklaven;
1115-30-6

diethyl acetylsuccinate

123-76-2

levulinic acid

Conditions
ConditionsYield
With hydrogenchloride for 2.5h; Heating; also by alkaline hydrolysis with 10percent aq. KOH;93%
With hydrogenchloride
With hydrogenchloride at 90℃; for 4h; Yield given;
1623-88-7

5-chloromethylfurfural

123-76-2

levulinic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 190℃; for 0.333333h; Sealed vessel;93%
With water at 190℃; for 0.333333h; sealed tube;91.2%
102390-86-3

5-(2-furaldehyde)methyl formate

123-76-2

levulinic acid

Conditions
ConditionsYield
In water at 120℃; for 4h; Sealed tube;92%
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    Product Name: Levulinic acid Synonyms: 3-acetyl-propionicaci;3-Keto-n-velericacid;4-Keto-n-valericacid;4-Oxo-pentanoic acid (levulinic acid);4-oxo-pentanoicaci;4-oxovaleric;4-oxo-valericaci;4-Oxpentanoicacid CAS: 123-76-2 MF: C5H8O3 MW: 116.12

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    Product Name: Levulinic acid CAS: 123-76-2 MF: C5H8O3 MW: 116.12 EINECS: 204-649-2 Mol File: 123-76-2.mol Levulinic acid Structure Levulinic acid Chemical Properties Melting point 30-33 °C (lit.) Boiling point 245-246

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Specification

Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH3C(O)CH2CH2CO2H. It is also named as β-Acetylpropionic acid; γ-Ketovaleric acid; Laevulinic acid; Levulic acid; 3-Acetylpropionic acid; 4-Ketovaleric acid; 4-Oxopentanoic acid; 4-Oxovaleric acid; Acetopropionic acid; LEVA. It is classified as a keto acid. This white crystalline is soluble in water and polar organic solvents. It is derived from degradation of cellulose and is a potential precursor to biofuels. Levulinic acid is a precursor to nylon-like polymers, synthetic rubbers, and plastics. And it is a versatile synthetic intermediate in the synthesis of pharmaceuticals. Besides, it is a precursor in the industrial production of other chemical commodities such as methyltetrahydrofuran, valerolactone, and ethyl levulinate.

Physical properties about Levulinic acid are: (1)ACD/LogP: -0.49; (2)ACD/LogD (pH 5.5): -1.29; (3)ACD/LogD (pH 7.4): -3.08; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 2.06; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.435; (12)Molar Refractivity: 26.807 cm3; (13)Molar Volume: 102.815 cm3; (14)Polarizability: 10.627 10-24cm3; (15)Surface Tension: 39.6129989624023 dyne/cm; (16)Density: 1.129 g/cm3; (17)Flash Point: 114.964 °C; (18)Enthalpy of Vaporization: 52.85 kJ/mol; (19)Boiling Point: 242.892 °C at 760 mmHg; (20)Vapour Pressure: 0.0109999999403954 mmHg at 25°C

Preparation of Levulinic acid: Levulinic acid is prepared in the laboratory by heating sucrose with concentrated hydrochloric acid. The process proceeds via the intermediacy of glucose, which is isomerized to fructose and then hydroxymethylfurfural. Other sugar-derivatives, such as levulose, inulin, starch, and other acids, e.g. sulfuric acids can also be used.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
3. Wear suitable protective clothing and gloves;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8);
(2)InChIKey=JOOXCMJARBKPKM-UHFFFAOYSA-N;
(3)SmilesC(CCC(O)=O)(C)=O;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 450mg/kg (450mg/kg)   National Technical Information Service. Vol. AD607-952,
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 847, 1979.
rat LD50 oral 1850mg/kg (1850mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 847, 1979.