D(+)-Malic acid supplier | CasNO.636-61-3

Name
D(+)-Malic acid
EINECS 211-262-2
CAS No. 636-61-3
Article Data55
CAS DataBase
Density 1.641 g/cm³
Solubility soluble in water
Melting Point 98-102 °C(lit.)
Formula C₄H₆O₅
Boiling Point 306.4 °C at 760 mmHg
Molecular Weight 134.089
Flash Point 153.4 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36-37/39
Risk Codes 37/38-41-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms D-malic acid;(R)-malate;L(+)-Malic acid;CPD-660;(R)-malic acid;D-Hydroxysuccinic acid;Malic acid, D-;Malic acid, L(+)-;(+)-D-malic acid;D-malate;(2R)-2-hydroxybutanedioic acid;
PSA 94.83000
LogP -1.09340

Synthetic route

: 56-84-8
L-Aspartic acid

A: 636-61-3
D-Malic acid

B: 4198-33-8
(2S)-chlorobutanedioic acid

C: 6915-18-0
2-butenedioic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at -15 - 0℃; for 8h;	A 0.1% B 86% C 0.1%
With hydrogenchloride; sodium chloride; sodium nitrite In water at -15 - 0℃; for 7h;	A 0.1 - 0.4 %Spectr. B 80% C 0.1%

...Expand

: 80513-23-1
(R)-4,4,4-trichloro-3-hydroxybutanoic acid

A: 636-61-3
D-Malic acid

B: 110-17-8
(2E)-but-2-enedioic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 24h;	A 79% B n/a

: 110-16-7
maleic acid

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With TETRACYCLINE In water at 37℃; for 18h; Clostridium formicoaceticum, phosphate buffer;	75%
biosynthesis by resting cells of Ustilago sphaerogena strain S402;
With 2-(cyclohexylamino)ethanesulfonic acid; potassium chloride; potassium hydroxide pH=9; Kinetics; Reagent/catalyst; Enzymatic reaction;

: 252330-06-6
malic acid-4-methylamide

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With barium dihydroxide

: 2058-58-4
(R)-Asparagine

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With cis-nitrous acid

: 70-47-3
L-asparagine

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With nitrogen oxides; acetic acid at 95℃;

: 617-48-1
malic acid

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
bei der enzymatischen Spaltung unter dem Einfluss von Hunde- oder Kaninchenmuskelbrei bleibt optisch unreine d(+)-Aepfelsaeure zurueck;
With Cinchonin
With rac-methylbenzylamine

: 16045-92-4
chlorosuccinic acid

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With silver nitrate
With silver(l) oxide
With water; potassium carbonate; silver nitrate
With alkali

: 16045-92-4
chlorosuccinic acid

A: 636-61-3
D-Malic acid

B: 97-67-6
(S)-Malic acid

Conditions

Conditions	Yield
With alkali Hydrolysis.bei der Hydrolyse der Dinatriumsalze;
With water Hydrolysis.bei der Hydrolyse der Dinatriumsalze;

: 923-06-8, 584-98-5
bromosuccinic acid

A: 636-61-3
D-Malic acid

B: 97-67-6
(S)-Malic acid

Conditions

Conditions	Yield
With alkali Hydrolysis.bei der Hydrolyse der Kupfer(II)-salze;
With water Hydrolysis.bei der Hydrolyse der Kupfer(II)-salze;
Hydrolysis.in saurer oder anfangs neutraler Loesung;

: 20629-30-5
iodo-succinic acid

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With ammonia

: 1783-96-6
(2R)-aspartic acid

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With cis-nitrous acid

: 14189-99-2, 24766-96-9, 59025-03-5, 79814-40-7
(R)-(+)-2-acetoxysuccinic anhydride

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With sodium hydroxide Ambient temperature;

: deacetylboronolide

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With potassium hydroxide; sodium periodate; ozone 1.) H2O, 16 h, room temperature, 2.) HOAc-HCOOH (9:1) 10 deg C, 110 deg C, 12 h, 3.) H2O, 30 min; Multistep reaction;

: (R)-4,4,4-Trichloro-3-(1-ethoxy-ethoxy)-butyric acid methyl ester

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
With sodium hydroxide for 48h; Heating;

: (+/-)-propylammonium hydrogen malate

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
In methanol at 10℃; Yield given;

: (+/-)-1,1,3,3-tetramethylbutylammonium hydrogen malate

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
In water at 10℃; Yield given;

: 7697-37-2
nitric acid

: 19444-84-9
3-hydroxyoxolan-2-one

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
at 45 - 50℃; lactone of/the/ dextrorotatory α.γ-dioxy-butyric acid;

: 7647-01-0
hydrogenchloride

: 67-56-1
methanol

: 72229-28-8
(2S,3S)-2-Acetoxy-3-chlor-bernsteinsaeuredimethylester

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
nachfolgenden Reduktion mit einem mit Platindraht umwickelten Zinkstab in Wasser.Hydrolysis;

...Expand

: 87-69-4
L-Tartaric acid

: 10034-85-2
hydrogen iodide

: 636-61-3
D-Malic acid

: 157543-57-2
(R)-2,4-dihydroxy-butyric acid

: 7697-37-2
nitric acid

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
at 45 - 50℃;

: 923-06-8, 584-98-5
bromosuccinic acid

: 302-01-2
hydrazine

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
beim Verseifen des Reaktionsprodukts; levorotatory bromo-succinic acid;

: 16045-92-4
chlorosuccinic acid

alkali: alkali

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
Dinatriumsalz reagiert; l(-)-chlorosuccinic acid;

: D-malic acid-4-propylamide

aqueous alkaline solution: aqueous alkaline solution

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
Hydrolysis;

: 82310-91-6
D-β-malamic acid

-base: -base

: 636-61-3
D-Malic acid

d-β-malamidoic acid: d-β-malamidoic acid

: 636-61-3
D-Malic acid

Conditions

Conditions	Yield
Verseifung;

: 67-56-1
methanol

: 636-61-3
D-Malic acid

: 70681-41-3
(R)-dimethyl malate

Conditions

Conditions	Yield
With thionyl chloride	100%
Stage #1: methanol With acetyl chloride at 0℃; for 1h; Stage #2: D-Malic acid at 20℃; for 16h;	100%
With thionyl chloride at 0 - 20℃; Inert atmosphere;	99%

: 636-61-3
D-Malic acid

: 70005-88-8
(R)-1,2,4-butanetriol

Conditions

Conditions	Yield
With Trimethyl borate; dimethylsulfide borane complex In tetrahydrofuran Inert atmosphere;	100%
With Trimethyl borate; dimethylsulfide borane complex In tetrahydrofuran for 20h; Ambient temperature;	98%
With Trimethyl borate; dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃;	97%

: 636-61-3
D-Malic acid

: 407-25-0
trifluoroacetic anhydride

: 83541-02-0
(R)-2,5-dioxotetrahydrofuran-3-yl 2,2,2-trifluoroacetate

Conditions

Conditions	Yield
at 20℃; for 4h; Cooling with ice; Inert atmosphere;	100%
at 0℃; for 2h;
for 2h; Ambient temperature;
at 0 - 20℃; for 3h;
for 2h;

: 636-61-3
D-Malic acid

: 135-19-3
β-naphthol

: (R)-(+)-malic acid di(2-naphthyl)ester

Conditions

Conditions	Yield
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine	100%
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In acetonitrile Esterification;

: 636-61-3
D-Malic acid

: 75-36-5
acetyl chloride

: 14189-99-2, 24766-96-9, 59025-03-5, 79814-40-7
(R)-(+)-2-acetoxysuccinic anhydride

Conditions

Conditions	Yield
at 45℃; for 6h;	100%
at 45℃; for 6h;	90%
at 45℃; for 6h;	90%

: 390800-88-1
bortezomib

: 636-61-3
D-Malic acid

: 1201902-99-9
2-((R)-2-((R)-3-methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)-5-oxo-1,3,2-dioxaborolan-4-yl)acetic acid

Conditions

Conditions	Yield
In acetone at 25℃; Heating;	100%

: 636-61-3
D-Malic acid

: 124-63-0
methanesulfonyl chloride

: 107314-06-7
(S)-methane-sulphonyloxysuccinic Acid

Conditions

Conditions	Yield
In tetrahydrofuran for 10h; Heating / reflux;	99%

: 636-61-3
D-Malic acid

: 11113-50-1
boric acid

: 1310-73-2
sodium hydroxide

: sodium (S,S,S)-dimalatoborate

Conditions

Conditions	Yield
In water malic acid dissolved in H2O, treated with boric acid, aq. NaOH added, stirred in open flask at 100 °C for ca. 4 h; mixt. evapd.; detd. by NMR, XRD;	99%

...Expand

: 636-61-3
D-Malic acid

: 1130137-76-6
(R,Z)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-hydroxy-3-morpholin-4-ylpropyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

: (R,Z)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (R)-malate

Conditions

Conditions	Yield
In methanol; water at 20 - 50℃; Darkness;	99%

: 67-56-1
methanol

: 636-61-3
D-Malic acid

: 83540-94-7
(3R)-3-hydroxy-4-methoxy-4-oxobutanoic acid

Conditions

Conditions	Yield
Stage #1: D-Malic acid With trifluoroacetic acid at 20℃; for 0.666667h; Inert atmosphere; Stage #2: methanol at 20℃; for 1.5h; Inert atmosphere;	99%
Stage #1: D-Malic acid With trifluoroacetic anhydride for 0.666667h; Stage #2: methanol at 20℃; for 1.5h;	84%
Stage #1: D-Malic acid With trifluoroacetic anhydride at 20℃; for 3h; Stage #2: methanol at 20℃;

: 636-61-3
D-Malic acid

: 11113-50-1
boric acid

: potassium hydroxide

: C8H8BO10(1-)*K(1+)

Conditions

Conditions	Yield
In water at 95℃;	99%

...Expand

: 636-61-3
D-Malic acid

: 630-19-3
pivalaldehyde

: 186906-71-8
2-((2R, 4R)-2-tert-butyl-5-oxo-1,3-dioxolan-4-yl) acetic acid

Conditions

Conditions	Yield
With sulfuric acid; toluene-4-sulfonic acid In pentane for 36h; Heating;	98%
With sulfuric acid; toluene-4-sulfonic acid In pentane for 6h; Heating;	92%
Stage #1: D-Malic acid With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at 23℃; Inert atmosphere; Stage #2: pivalaldehyde With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -25℃; Inert atmosphere;	82%

: 636-61-3
D-Malic acid

: 108-94-1
cyclohexanone

: 632357-87-0
2-[(4R)-2-cyclohexylidene-5-oxo-1,3-dioxolan-4-yl]acetic acid

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at 0 - 20℃; for 19h;	98%
With boron trifluoride diethyl etherate In diethyl ether at 0 - 20℃; for 25h;	93%
With boron trifluoride diethyl etherate In diethyl ether at 0 - 20℃; for 25h;
With boron trifluoride diethyl etherate In diethyl ether at 0 - 20℃; for 20h;
Stage #1: D-Malic acid; cyclohexanone With boron trifluoride diethyl etherate In diethyl ether at 0 - 20℃; for 97h; Stage #2: With water; sodium acetate In diethyl ether for 2h;

: 64-17-5
ethanol

: 636-61-3
D-Malic acid

: 7554-28-1
diethyl (R)-malate

Conditions

Conditions	Yield
With thionyl chloride Esterification;	97%
With thionyl chloride for 7h; Reflux;	95%
With sulfuric acid at 90℃; for 12h; Inert atmosphere;	95%

: 636-61-3
D-Malic acid

: 77-76-9
2,2-dimethoxy-propane

: 73991-95-4, 114458-03-6, 119618-59-6, 113278-68-5
2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate at 25℃;	97%
With pyridinium p-toluenesulfonate for 48h; Ambient temperature;	96%
With toluene-4-sulfonic acid In dichloromethane for 4h; Ambient temperature;	90%

: 636-61-3
D-Malic acid

: 482-20-2
(S)-(+)-tylophorine

: C24H27NO4*C4H6O5

Conditions

Conditions	Yield
In methanol; dichloromethane at 20℃; for 8h;	97%

: 636-61-3
D-Malic acid

: 100-51-6
benzyl alcohol

: 99266-22-5
(R)-dibenzyl 2-hydroxysuccinate

Conditions

Conditions	Yield
With 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt	95%
With toluene-4-sulfonic acid In toluene Heating;	95%

: 302-17-0
chloral hydrate

: 636-61-3
D-Malic acid

: (2RS,5R)-5-carboxymethyl-2-trichloromethyl-4-oxo-1,3-dioxolane

Conditions

Conditions	Yield
With sulfuric acid at 20℃; for 3h;	95%

: 636-61-3
D-Malic acid

: 75-36-5
acetyl chloride

: 7554-28-1
diethyl (R)-malate

Conditions

Conditions	Yield
In ethanol at 20℃; for 69h;	95%

: 636-61-3
D-Malic acid

: 441785-25-7
Besifovir

: C4H6O5*2C10H14N5O4P

Conditions

Conditions	Yield
In methanol at 15 - 45℃;	93.51%

: 636-61-3
D-Malic acid

: 252639-05-7
5-bromo-3-(N,N-dimethylaminomethyl)-N-methylindole

: 1-methyl-5-bromogramine D-malate

Conditions

Conditions	Yield
In methanol for 2h; Reflux;	93%

: 636-61-3
D-Malic acid

: 100-51-6
benzyl alcohol

: 83477-74-1
2-R-hydroxysuccinic acid 1-benzylester

Conditions

Conditions	Yield
With trifluoroacetic anhydride Inert atmosphere;	92%
Stage #1: D-Malic acid With trifluoroacetic anhydride at 0℃; Stage #2: benzyl alcohol at 20℃; Further stages.;	86%
Stage #1: D-Malic acid With trifluoroacetic anhydride at 0℃; for 2.5h; Stage #2: benzyl alcohol at 20℃; for 2h;
Stage #1: D-Malic acid With trifluoroacetic anhydride at 20℃; for 4h; Cooling; Stage #2: benzyl alcohol	28 g

: tetraethylammonium hydroxide

: 12125-77-8
tricarbonyl(cycloheptatriene)molybdenum(0)

: 636-61-3
D-Malic acid

: [Et4N]2[(D-mallic acid(-2H))Mo(CO)3]

Conditions

Conditions	Yield
In methanol (N2); Schlenk technique; soln. of Et4OH in MeOH was added dropwise with stirring to soln. of acid in MeOH at room temp.; solvent was removed (vac.); dissolved in MeOH; obtained soln. was added to soln. of Mo complex in MeOH; mixt. was stirred overnight; solvent removed (vac.); extd. (MeCN/MeOH); layered with ether; elem. anal.;	90%

...Expand

: 636-61-3
D-Malic acid

: 2393-23-9
4-methoxy-benzylamine

: 1312764-95-6
(R)-3-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 8h; Reflux; optical yield given as %ee;	90%
In m-xylene Reflux;	78%

: 636-61-3
D-Malic acid

: 1218935-59-1
(R)-(+)-2-(2,5-difluorophenyl)pyrrolidine

: (R)-2-(2,5-difluorophenyl)-pyrrolidine (R)-2-hydroxy-succinate

Conditions

Conditions	Yield
With triethylamine In ethanol at 20 - 65℃; Inert atmosphere;	90%

: 636-61-3
D-Malic acid

: 138729-47-2
eszopiclone

: 863393-46-8
(S)-(+)-6-(5-chloro-2-pyridinyl)-7-(4-methylpiperazin-1-yl-carbonyloxy)-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazine-5-one D-(+)-malate

Conditions

Conditions	Yield
In ethyl acetate for 18h;	89%

: 64-17-5
ethanol

: 636-61-3
D-Malic acid

: 83540-96-9
(R)-2-Hydroxy-succinic acid 1-ethyl ester

Conditions

Conditions	Yield
With salicylaldehyde at 80℃; for 14h; Inert atmosphere; chemoselective reaction;	89%

: 636-61-3
D-Malic acid

: 43200-80-2
zopiclon

: 863393-46-8
(S)-(+)-6-(5-chloro-2-pyridinyl)-7-(4-methylpiperazin-1-yl-carbonyloxy)-6,7-dihydro-5h-pyrrolo[3,4-b]pyrazine-5-one D-(+)-malate

Conditions

Conditions	Yield
In methanol; acetone at 10 - 48℃; for 4h;	88%
In methanol; acetone at 55 - 56℃; for 0.5h; Product distribution / selectivity;	41%

: 617-48-1
malic acid

: 636-61-3
D-Malic acid

: 32082-74-9
(R)-4-methyloxetan-2-one

Conditions

Conditions	Yield
With hydrogenchloride; sodium borohydrid; lithium chloride In tetrahydrofuran; methanol	88%

: 636-61-3
D-Malic acid

: 2393-23-9
4-methoxy-benzylamine

: 75-36-5
acetyl chloride

: (R)-1-(4-methoxybenzyl)-2,5-dioxopyrrolidin-3-yl acetate

Conditions

Conditions	Yield
Stage #1: D-Malic acid; acetyl chloride for 20h; Reflux; Stage #2: 4-methoxy-benzylamine In tetrahydrofuran at 0 - 25℃; for 18h;	87%
Stage #1: D-Malic acid; acetyl chloride Reflux; Stage #2: 4-methoxy-benzylamine With acetyl chloride In dichloromethane Reflux; Stage #3: With acetyl chloride In dichloromethane Reflux;
Stage #1: D-Malic acid; acetyl chloride for 16h; Reflux; Stage #2: 4-methoxy-benzylamine In tetrahydrofuran at 20℃; for 18h; Stage #3: acetyl chloride for 18h; Reflux;	660 mg

...Expand

D(+)-Malic acid Specification

The D(+)-Malic acid is an organic compound with the formula C₄H₆O₅. The IUPAC name of this chemical is (2R)-2-hydroxybutanedioic acid. With the CAS registry number 636-61-3, it is also named as Butanedioic acid, 2-hydroxy-, (2R)-. The product's categories are Fine Chemical & Intermediates; Food & Feed Additives; MalicAcidSeries; Chiral; API Intermediates; All Aliphatics; Carboxylic Acids (Chiral); Chiral Building Blocks; For Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Chiral Chemicals; Chiral Compound; Aliphatics; Chiral Reagents. Besides, it is a white to light yellow crystal powder, which should be stored in a cool and dry place. It can be used for chiral drug, chiral additive, chiral auxiliarie, etc.

Physical properties about D(+)-Malic acid are: (1)ACD/LogP: -1.26; (2)ACD/LogD (pH 5.5): -4.43; (3)ACD/LogD (pH 7.4): -6; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 61.83 Å²; (12)Index of Refraction: 1.529; (13)Molar Refractivity: 25.2 cm³; (14)Molar Volume: 81.6 cm³; (15)Polarizability: 9.99×10^-24cm³; (16)Surface Tension: 86.2 dyne/cm; (17)Density: 1.641 g/cm³; (18)Flash Point: 153.4 °C; (19)Enthalpy of Vaporization: 63.43 kJ/mol; (20)Boiling Point: 306.4 °C at 760 mmHg; (21)Vapour Pressure: 7.19E-05 mmHg at 25°C.

Uses of D(+)-Malic acid: it can be used to produce malic acid diethyl ester. It will need reagent HCl.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is risk of serious damage to eyes. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)C[C@@H](O)C(=O)O
(2)InChI: InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
(3)InChIKey: BJEPYKJPYRNKOW-UWTATZPHBO
(4)Std. InChI: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
(5)Std. InChIKey: BJEPYKJPYRNKOW-UWTATZPHSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LDLo	oral	5500mg/kg (5500mg/kg)		Industrial and Engineering Chemistry. Vol. 15, Pg. 628, 1923.

Product Name

D(+)-Malic acid

Synthetic route

D(+)-Malic acid Specification

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