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Malondialdehyde

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Name

Malondialdehyde

EINECS N/A
CAS No. 542-78-9 Density 0.991g/cm3
PSA 34.14000 LogP -0.22570
Solubility N/A Melting Point 72-74°
Formula C3H4 O2 Boiling Point 108.3°Cat760mmHg
Molecular Weight 72.0636 Flash Point 28.9°C
Transport Information N/A Appearance N/A
Safety Moderately toxic by ingestion. Questionable carcinogen with experimental carcinogenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES. Risk Codes N/A
Molecular Structure Molecular Structure of 542-78-9 (propanedial) Hazard Symbols N/A
Synonyms

Malonaldehyde(6CI,8CI);1,3-Propanedialdehyde;Diformylmethane;MDA;Malondialdehyde;Malonic aldehyde;Malonic dialdehyde;Malonodialdehyde;Malonyldialdehyde;

Article Data 64

Malondialdehyde Synthetic route

17887-80-8

1,3-bis(trimethylsiloxy)propane

542-78-9

Malondialdehyde

Conditions
ConditionsYield
With chromium(VI) oxide; HZSM-5 zeolite for 0.025h; microwave irradiation;99%
113331-81-0, 113331-84-3, 114738-36-2

(1R*,4R*,5S*)-5-phenyl-2,3-dioxabicyclo<2.2.1>heptane

A

292638-84-7

styrene

B

542-78-9

Malondialdehyde

113331-87-6

(3RS,4SR)-3-hydroxy-4-phenyl-1-cyclopentanone

113331-88-7, 120708-35-2, 120708-36-3

(3SR,4SR)-4,5-epoxy-3-phenyl-1-pentanal

113331-85-4, 114817-51-5, 114817-54-8, 114817-56-0, 120708-38-5

(1R*,3R*,4S*)-4-phenylcyclopentane-1,3-diol

113331-86-5, 113428-36-7, 113428-37-8, 113428-41-4, 119238-85-6

(2ξ,4RS,6SR)-6-phenyltetrahydropyran-2,4-diol

Conditions
ConditionsYield
With iron(II) sulfate In water; acetonitrile at 0℃; for 0.5h; Product distribution; Mechanism;A 45%
B 39%
C 6%
D 10%
E n/a
F n/a
63942-75-6

PGH2 methyl ester

A

542-78-9

Malondialdehyde

B

79171-56-5

(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid methyl ester

Conditions
ConditionsYield
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 19℃; for 4h;A 41%
B n/a
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 19℃; for 4h;
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 19℃; for 4h; Product distribution; ruthenium(II) catalyzed reaction of 1,4-endoperoxide;
279-35-6

1,3-epiperoxycyclopentane

A

542-78-9

Malondialdehyde

B

65842-25-3

3-oxiranepropanal

C

74-85-1

ethene

D

16326-97-9

cis-cyclopentane-1,3-diol

E

26831-63-0

rac-3-hydroxycyclopentanone

Conditions
ConditionsYield
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane-d2 at 0℃; for 0.25h; Product distribution; ruthenium(II) catalyzed reactions of 1,4-endoperoxide;A 16%
B 38%
C 31%
D 9%
E 1%
113331-81-0, 113331-84-3, 114738-36-2

(1R*,4R*,5S*)-5-phenyl-2,3-dioxabicyclo<2.2.1>heptane

A

292638-84-7

styrene

B

542-78-9

Malondialdehyde

113331-87-6

(3RS,4SR)-3-hydroxy-4-phenyl-1-cyclopentanone

113331-88-7, 120708-35-2, 120708-36-3

(3SR,4SR)-4,5-epoxy-3-phenyl-1-pentanal

Conditions
ConditionsYield
With iron(II) sulfate In chloroform for 0.5h; Yield given;A 45 % Chromat.
B n/a
C 6%
D 10%
With iron(II) sulfate In acetonitrile for 30h;A 45 % Chromat.
B n/a
C 6%
D 10%
113331-81-0, 113331-84-3, 114738-36-2

(1R*,4R*,5S*)-5-phenyl-2,3-dioxabicyclo<2.2.1>heptane

A

292638-84-7

styrene

B

542-78-9

Malondialdehyde

113331-87-6

(3RS,4SR)-3-hydroxy-4-phenyl-1-cyclopentanone

113331-88-7, 120708-35-2, 120708-36-3

(3SR,4SR)-4,5-epoxy-3-phenyl-1-pentanal

113331-85-4, 114817-51-5, 114817-54-8, 114817-56-0, 120708-38-5

(1R*,3R*,4S*)-4-phenylcyclopentane-1,3-diol

F

119238-85-6

6-Phenyl-tetrahydro-pyran-2,4-diol

Conditions
ConditionsYield
With iron(II) sulfate In acetonitrile for 0.5h; Product distribution; further electron transfer reag.; var. solv. and time;A 45 % Chromat.
B n/a
C 6%
D 10%
E 1%
F n/a
122-31-6

malondialdehyde bis(diethyl acetal)

542-78-9

Malondialdehyde

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
With hydrogenchloride In water at 40℃; for 0.666667h;
927-63-9

3-dimethylaminoacrolein

542-78-9

Malondialdehyde

Conditions
ConditionsYield
With sodium hydroxide
16545-68-9

cyclopropanol

542-78-9

Malondialdehyde

Conditions
ConditionsYield
With chromium(VI) oxide at 25℃; Rate constant;

Malondialdehyde Consensus Reports

Consensus of Propanedial (542-78-9):
IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 36 ,1985,p. 163.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Malondialdehyde Specification

Malondialdehyde is the organic compound with the formula CH2(CHO)2. With the CAS NO.542-78-9, it is also called propanedial; 1,3-Propanedione; 3-Oxopropanal; Malonyl dialdehyde. Malondialdehyde is a highly reactive compound that is not typically observed in pure form. Malondialdehyde is generated from reactive oxygen species (ROS), and as such is assayed in vivo as a bio-marker of oxidative stress.

Physical properties about Malondialdehyde are: (1)ACD/LogP: -0.987; (2)ACD/LogD (pH 5.5): -2.05; (3)ACD/LogD (pH 7.4): -3.35; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.367; (11)Molar Refractivity: 16.321 cm3; (12)Molar Volume: 72.693 cm3; (13)Polarizability: 6.47 10-24cm3; (14)Surface Tension: 29.3999996185303 dyne/cm; (15)Density: 0.991 g/cm3; (16)Flash Point: 28.881 °C; (17)Enthalpy of Vaporization: 34.713 kJ/mol; (18)Boiling Point: 108.332 °C at 760 mmHg; (19)Vapour Pressure: 26.0349998474121 mmHg at 25°C

You can still convert the following datas into molecular structure:
(1)InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2;
(2)InChIKey=WSMYVTOQOOLQHP-UHFFFAOYSA-N;
(3)SmilesC(C=O)C=O;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 606mg/kg (606mg/kg)   Acta Universitatis Ouluensis, Series D: Medica. Vol. 55, Pg. 3, 1980.
rat LD50 oral 632mg/kg (632mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: MUSCLE WEAKNESS
Toxicology and Applied Pharmacology. Vol. 7, Pg. 826, 1965.

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