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DL-Malic acid

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Name

DL-Malic acid

EINECS 210-514-9
CAS No. 617-48-1 Density 1.641 g/cm3
PSA 94.83000 LogP -1.09340
Solubility 558 g/L (20℃) Melting Point 130-132oC
Formula C4H6O5 Boiling Point 306.4oC at 760 mmHg
Molecular Weight 134.089 Flash Point 203oC
Transport Information N/A Appearance White to nearly white crystals or crystal powder
Safety Risk Codes  Xi:Irritant;
Molecular Structure Molecular Structure of 617-48-1 (Malic acid) Hazard Symbols R22:; R34:; R42/43:;
Synonyms

DL-Hydroxysuccinic acid;DL-2-Hydroxybutanedioic acid;DL-Apple acid;

Article Data 154

DL-Malic acid Synthetic route

110-16-7

maleic acid

A

109-99-9

tetrahydrofuran

B

96-48-0

4-butanolide

C

67-56-1

methanol

D

110-63-4

Butane-1,4-diol

E

617-48-1

malic acid

F

110-15-6

succinic acid

G

64-19-7

acetic acid

H

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;A 0.45%
B 0.06%
C 0%
D 0.21%
E 0.36%
F 98.73%
G 0.04%
H 0.08%
110-17-8

(2E)-but-2-enedioic acid

617-48-1

malic acid

Conditions
ConditionsYield
With sodium; iron97%
With water at 150 - 200℃;
With sodium hydroxide; water at 100℃;
97-99-4

Tetrahydrofurfuryl alcohol

150-90-3

sodium succinate

A

617-48-1

malic acid

B

(tetrahydrofuran-2-ylmethoxy)butanedioic acid

Conditions
ConditionsYield
With lanthanum(III) chloride at 116℃; for 19h; Product distribution; also with other alcohols; variation of reaction time, temperature and proportion of reagents;A 3%
B 95%
67-56-1

methanol

A

617-48-1

malic acid

B

1726-80-3

2-methoxy succinic acid

Conditions
ConditionsYield
With lanthanum(III) chloride; trimethyl orthoformate In water at 150℃; for 6h;A 1.5 % Chromat.
B 91%
110-16-7

maleic acid

A

109-99-9

tetrahydrofuran

B

96-48-0

4-butanolide

C

110-63-4

Butane-1,4-diol

D

591-81-1

4-hydroxybutanoic acid

E

617-48-1

malic acid

F

110-15-6

succinic acid

G

64-19-7

acetic acid

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd/2.0percent Re on Rutile TiO2 at 110℃; Product distribution / selectivity;A 1.27%
B 4.78%
C 1.55%
D 1.24%
E 0.48%
F 90.6%
G 0.08%
110-16-7

maleic acid

A

109-99-9

tetrahydrofuran

B

96-48-0

4-butanolide

C

110-63-4

Butane-1,4-diol

D

617-48-1

malic acid

E

110-15-6

succinic acid

F

64-19-7

acetic acid

G

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; for 96 - 238h; Product distribution / selectivity;A 0.6%
B 0.04%
C 0.62%
D 0.19%
E 88.49%
F 0.12%
G 0.11%
110-16-7

maleic acid

A

109-99-9

tetrahydrofuran

B

96-48-0

4-butanolide

C

110-63-4

Butane-1,4-diol

D

591-81-1

4-hydroxybutanoic acid

E

617-48-1

malic acid

F

110-15-6

succinic acid

G

100-21-0

terephthalic acid

H

64-19-7

acetic acid

I

802294-64-0

propionic acid

J

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With hydrogen; 0.5percent Pd/0.2percent Re on Rutile TiO2 at 110℃; for 170 - 1009h; Product distribution / selectivity;A 0.86%
B 4.34%
C 0.28%
D 1.24%
E 0%
F 85.51%
G 0%
H 0.04%
I 0%
J 0%
1631-28-3

N-p-tolylphenylmaleimide

617-48-1

malic acid

Conditions
ConditionsYield
Stage #1: N-p-tolylphenylmaleimide With potassium carbonate; isopropyl alcohol for 1h; oxa-Michael addition; Heating;
Stage #2: With hydrogenchloride; acetic acid for 10h; Heating;
85%
98-01-1

furfural

A

617-48-1

malic acid

B

110-16-7

maleic acid

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid; 5 weight percent methyltrioxorhenium on polystyrene In water at 20℃; Product distribution / selectivity;A 9%
B 84%
108-31-6

maleic anhydride

A

617-48-1

malic acid

B

110-17-8

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With water at 190℃; for 1h; Temperature; Concentration; Time; Sealed tube; Green chemistry;A n/a
B 72%

DL-Malic acid Chemical Properties

The Molecular Structure of DL-Malic acid (CAS NO.617-48-1):

Empirical Formula: C4H6O5
Molecular Weight: 134.0874
IUPAC Name: 2-hydroxybutanedioic acid    
Appearance:  white crystalline powder 
Nominal Mass: 134 Da
Average Mass: 134.0874 Da
Monoisotopic Mass: 134.021523 Da
Index of Refraction: 1.529
Molar Refractivity: 25.2 cm3
Molar Volume: 81.6 cm3
Surface Tension: 86.2 dyne/cm
Density: 1.641 g/cm3
Flash Point: 153.4 °C
Enthalpy of Vaporization: 63.43 kJ/mol
Boiling Point: 306.4 °C at 760 mmHg
Vapour Pressure: 7.19E-05 mmHg at 25°C
Product Categories: MalicAcidSeries 
Solubility methanol: 0.1 g/mL, clear, colorless
Stability: Stable. Incompatible with strong oxidizing agents, strong bases, amines, alkali metals, carbonates
Synonyms:  (+/-)-2-Hydroxysuccinic acid ; (+/-)-Hydroxybutanedioic acid ; (+/-)-Hydroxysuccinic acid ; Dl-2-hydroxybutanedioic acid ; Dl-hyroxybutanedioic acid ; Dl-hydroxysuccinic acid ; Dl-hydroxysucoinic acid ; Dl(+/-)-malic acid               

DL-Malic acid Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4937, 1982.
mouse LD50 oral 1600mg/kg (1600mg/kg)   Kodak Company Reports. Vol. #82-0458,
rat LD50 intraperitoneal 100mg/kg (100mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4937, 1982.
LD50/LC50: RTECS:
CAS# 6915-15-7: Draize test, rabbit, eye: 750 ug/24H Severe;
Draize test, rabbit, skin: 20 mg/24H Moderate;
Oral, mouse: LD50 = 1600 mg/kg;
Carcinogenicity: DL-Malic acid - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Other: The toxicological properties have not been fully investigated. See actual entry in RTECS for complete information. 

DL-Malic acid Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 22-37/38-41-42/43-34 
R22: Harmful if swallowed
R37/38: Irritating to respiratory system and skin
R41: Risk of serious damage to the eyes
R42/43: May cause sensitization by inhalation and skin contact
R34: Causes burns
Safety Statements: 26-39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S39: Wear eye / face protection
WGK Germany: 1
RTECS: ON7175000

DL-Malic acid Specification

Product Categories: MalicAcidSeries
Personal Protection:Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure.
Fire Fighting:Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extinguishing media: Use agent most appropriate to extinguish fire. In case of fire use water spray, dry chemical, carbon dioxide, or appropriate foam.
 

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