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636-61-3

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636-61-3 Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 636-61-3 differently. You can refer to the following data:
1. The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid rece
2. D-(+)-Malic acid used as an acidulant and flavoring agent, food additive. And it is also used in the place of the less sour citric acid in sour sweets.
3. D-(+)-Malic acid can be used: As a starting material for the enantioselective total synthesis of (?)-erinapyrone B.As a chiral organocatalyst in the synthesis of α-aminophosphonates from various aldehydes, aniline, and diethyl phosphite.

Definition

ChEBI: An optically active form of malic acid having (R)-configuration.

Biological Activity

D-(+)-Malic acid, an active isomer of Malic acid, is a competitive inhibitor of L(--)malic acid transport.

Synthesis

Malic acid is isolated from immature apples; industrially prepared is obtained by catalytic oxidation of benzene, then reacting with water at high temperature and high pressure to generate maleic anhydride.

in vitro

Some bacteria belonging to Arthrobacter, Brevibacterium, Corynebacterium, Pseudomonas, Bacillus, and Acinetobacter produced D-(+)-Malic acid (D-Malic acid) from Maleic acid when the cells grown in a medium containing citraconic acid are reacted aerobically with Maleic acid in the pH 7.0 phosphate buffer containing 0.1% sodium chloride.

Check Digit Verification of cas no

The CAS Registry Mumber 636-61-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 6 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 636-61:
(5*6)+(4*3)+(3*6)+(2*6)+(1*1)=73
73 % 10 = 3
So 636-61-3 is a valid CAS Registry Number.
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

636-61-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • TCI America

  • (M0021)  D-(+)-Malic Acid  >98.0%(GC)(T)

  • 636-61-3

  • 5g

  • 350.00CNY

  • Detail
  • TCI America

  • (M0021)  D-(+)-Malic Acid  >98.0%(GC)(T)

  • 636-61-3

  • 25g

  • 1,200.00CNY

  • Detail
  • Alfa Aesar

  • (A11688)  D-(+)-Malic acid, 98+%   

  • 636-61-3

  • 1g

  • 158.0CNY

  • Detail
  • Alfa Aesar

  • (A11688)  D-(+)-Malic acid, 98+%   

  • 636-61-3

  • 5g

  • 314.0CNY

  • Detail
  • Alfa Aesar

  • (A11688)  D-(+)-Malic acid, 98+%   

  • 636-61-3

  • 25g

  • 942.0CNY

  • Detail
  • Sigma-Aldrich

  • (02300)  D-(+)-Malicacid  unnatural form, ≥97.0% (T)

  • 636-61-3

  • 02300-1G

  • 705.51CNY

  • Detail
  • Sigma-Aldrich

  • (02300)  D-(+)-Malicacid  unnatural form, ≥97.0% (T)

  • 636-61-3

  • 02300-5G

  • 811.98CNY

  • Detail
  • Sigma-Aldrich

  • (02300)  D-(+)-Malicacid  unnatural form, ≥97.0% (T)

  • 636-61-3

  • 02300-25G

  • 5,062.59CNY

  • Detail
  • Supelco

  • (46940-U)  D-Malicacid  analytical standard

  • 636-61-3

  • 46940-U

  • 313.56CNY

  • Detail

636-61-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-malic acid

1.2 Other means of identification

Product number -
Other names D-malate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:636-61-3 SDS

636-61-3Synthetic route

L-Aspartic acid
56-84-8

L-Aspartic acid

A

D-Malic acid
636-61-3

D-Malic acid

B

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

(2S)-chlorobutanedioic acid

C

2-butenedioic acid
6915-18-0

2-butenedioic acid

Conditions
ConditionsYield
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%
(R)-4,4,4-trichloro-3-hydroxybutanoic acid
80513-23-1

(R)-4,4,4-trichloro-3-hydroxybutanoic acid

A

D-Malic acid
636-61-3

D-Malic acid

B

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

(2E)-but-2-enedioic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 24h;A 79%
B n/a
maleic acid
110-16-7

maleic acid

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
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;
malic acid-4-methylamide
252330-06-6

malic acid-4-methylamide

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
With barium dihydroxide
(R)-Asparagine
2058-58-4

(R)-Asparagine

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
With cis-nitrous acid
L-asparagine
70-47-3

L-asparagine

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
With nitrogen oxides; acetic acid at 95℃;
malic acid
617-48-1

malic acid

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
bei der enzymatischen Spaltung unter dem Einfluss von Hunde- oder Kaninchenmuskelbrei bleibt optisch unreine d(+)-Aepfelsaeure zurueck;
With Cinchonin
With rac-methylbenzylamine
chlorosuccinic acid
16045-92-4

chlorosuccinic acid

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
With silver nitrate
With silver(l) oxide
With water; potassium carbonate; silver nitrate
With alkali
chlorosuccinic acid
16045-92-4

chlorosuccinic acid

A

D-Malic acid
636-61-3

D-Malic acid

B

(S)-Malic acid
97-67-6

(S)-Malic acid

Conditions
ConditionsYield
With alkali Hydrolysis.bei der Hydrolyse der Dinatriumsalze;
With water Hydrolysis.bei der Hydrolyse der Dinatriumsalze;
bromosuccinic acid
923-06-8, 584-98-5

bromosuccinic acid

A

D-Malic acid
636-61-3

D-Malic acid

B

(S)-Malic acid
97-67-6

(S)-Malic acid

Conditions
ConditionsYield
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;
iodo-succinic acid
20629-30-5

iodo-succinic acid

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
With ammonia
(2R)-aspartic acid
1783-96-6

(2R)-aspartic acid

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
With cis-nitrous acid
(R)-(+)-2-acetoxysuccinic anhydride
14189-99-2, 24766-96-9, 59025-03-5, 79814-40-7

(R)-(+)-2-acetoxysuccinic anhydride

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature;
deacetylboronolide

deacetylboronolide

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
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

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

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
With sodium hydroxide for 48h; Heating;
(+/-)-propylammonium hydrogen malate

(+/-)-propylammonium hydrogen malate

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
In methanol at 10℃; Yield given;
(+/-)-1,1,3,3-tetramethylbutylammonium hydrogen malate

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

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
In water at 10℃; Yield given;
nitric acid
7697-37-2

nitric acid

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

3-hydroxyoxolan-2-one

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
at 45 - 50℃; lactone of/the/ dextrorotatory α.γ-dioxy-butyric acid;
hydrogenchloride
7647-01-0

hydrogenchloride

methanol
67-56-1

methanol

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

(2S,3S)-2-Acetoxy-3-chlor-bernsteinsaeuredimethylester

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
nachfolgenden Reduktion mit einem mit Platindraht umwickelten Zinkstab in Wasser.Hydrolysis;
L-Tartaric acid
87-69-4

L-Tartaric acid

hydrogen iodide
10034-85-2

hydrogen iodide

D-Malic acid
636-61-3

D-Malic acid

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

(R)-2,4-dihydroxy-butyric acid

nitric acid
7697-37-2

nitric acid

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
at 45 - 50℃;
bromosuccinic acid
923-06-8, 584-98-5

bromosuccinic acid

hydrazine
302-01-2

hydrazine

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
beim Verseifen des Reaktionsprodukts; levorotatory bromo-succinic acid;
chlorosuccinic acid
16045-92-4

chlorosuccinic acid

alkali

alkali

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
Dinatriumsalz reagiert; l(-)-chlorosuccinic acid;
D-malic acid-4-propylamide

D-malic acid-4-propylamide

aqueous alkaline solution

aqueous alkaline solution

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
Hydrolysis;
D-β-malamic acid
82310-91-6

D-β-malamic acid

-base

-base

D-Malic acid
636-61-3

D-Malic acid

d-β-malamidoic acid

d-β-malamidoic acid

D-Malic acid
636-61-3

D-Malic acid

Conditions
ConditionsYield
Verseifung;
methanol
67-56-1

methanol

D-Malic acid
636-61-3

D-Malic acid

(R)-dimethyl malate
70681-41-3

(R)-dimethyl malate

Conditions
ConditionsYield
With thionyl chloride100%
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%
D-Malic acid
636-61-3

D-Malic acid

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

(R)-1,2,4-butanetriol

Conditions
ConditionsYield
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%
D-Malic acid
636-61-3

D-Malic acid

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

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

(R)-2,5-dioxotetrahydrofuran-3-yl 2,2,2-trifluoroacetate

Conditions
ConditionsYield
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;
D-Malic acid
636-61-3

D-Malic acid

β-naphthol
135-19-3

β-naphthol

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

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

Conditions
ConditionsYield
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine100%
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In acetonitrile Esterification;
D-Malic acid
636-61-3

D-Malic acid

acetyl chloride
75-36-5

acetyl chloride

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

(R)-(+)-2-acetoxysuccinic anhydride

Conditions
ConditionsYield
at 45℃; for 6h;100%
at 45℃; for 6h;90%
at 45℃; for 6h;90%
bortezomib
390800-88-1

bortezomib

D-Malic acid
636-61-3

D-Malic acid

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
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
ConditionsYield
In acetone at 25℃; Heating;100%
D-Malic acid
636-61-3

D-Malic acid

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

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

(S)-methane-sulphonyloxysuccinic Acid

Conditions
ConditionsYield
In tetrahydrofuran for 10h; Heating / reflux;99%
D-Malic acid
636-61-3

D-Malic acid

boric acid
11113-50-1

boric acid

sodium hydroxide
1310-73-2

sodium hydroxide

sodium (S,S,S)-dimalatoborate

sodium (S,S,S)-dimalatoborate

Conditions
ConditionsYield
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%
D-Malic acid
636-61-3

D-Malic acid

(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
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

(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
ConditionsYield
In methanol; water at 20 - 50℃; Darkness;99%
methanol
67-56-1

methanol

D-Malic acid
636-61-3

D-Malic acid

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

(3R)-3-hydroxy-4-methoxy-4-oxobutanoic acid

Conditions
ConditionsYield
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℃;
D-Malic acid
636-61-3

D-Malic acid

boric acid
11113-50-1

boric acid

potassium hydroxide

potassium hydroxide

C8H8BO10(1-)*K(1+)

C8H8BO10(1-)*K(1+)

Conditions
ConditionsYield
In water at 95℃;99%
D-Malic acid
636-61-3

D-Malic acid

pivalaldehyde
630-19-3

pivalaldehyde

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

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

Conditions
ConditionsYield
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%
D-Malic acid
636-61-3

D-Malic acid

cyclohexanone
108-94-1

cyclohexanone

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

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

Conditions
ConditionsYield
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;
ethanol
64-17-5

ethanol

D-Malic acid
636-61-3

D-Malic acid

diethyl (R)-malate
7554-28-1

diethyl (R)-malate

Conditions
ConditionsYield
With thionyl chloride Esterification;97%
With thionyl chloride for 7h; Reflux;95%
With sulfuric acid at 90℃; for 12h; Inert atmosphere;95%
D-Malic acid
636-61-3

D-Malic acid

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

2,2-dimethoxy-propane

2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid
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
ConditionsYield
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%
D-Malic acid
636-61-3

D-Malic acid

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

(S)-(+)-tylophorine

C24H27NO4*C4H6O5

C24H27NO4*C4H6O5

Conditions
ConditionsYield
In methanol; dichloromethane at 20℃; for 8h;97%
D-Malic acid
636-61-3

D-Malic acid

benzyl alcohol
100-51-6

benzyl alcohol

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

(R)-dibenzyl 2-hydroxysuccinate

Conditions
ConditionsYield
With 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt95%
With toluene-4-sulfonic acid In toluene Heating;95%
chloral hydrate
302-17-0

chloral hydrate

D-Malic acid
636-61-3

D-Malic acid

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

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

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 3h;95%
D-Malic acid
636-61-3

D-Malic acid

acetyl chloride
75-36-5

acetyl chloride

diethyl (R)-malate
7554-28-1

diethyl (R)-malate

Conditions
ConditionsYield
In ethanol at 20℃; for 69h;95%
D-Malic acid
636-61-3

D-Malic acid

Besifovir
441785-25-7

Besifovir

C4H6O5*2C10H14N5O4P

C4H6O5*2C10H14N5O4P

Conditions
ConditionsYield
In methanol at 15 - 45℃;93.51%
D-Malic acid
636-61-3

D-Malic acid

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

5-bromo-3-(N,N-dimethylaminomethyl)-N-methylindole

1-methyl-5-bromogramine D-malate

1-methyl-5-bromogramine D-malate

Conditions
ConditionsYield
In methanol for 2h; Reflux;93%
D-Malic acid
636-61-3

D-Malic acid

benzyl alcohol
100-51-6

benzyl alcohol

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

2-R-hydroxysuccinic acid 1-benzylester

Conditions
ConditionsYield
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

tetraethylammonium hydroxide

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

tricarbonyl(cycloheptatriene)molybdenum(0)

D-Malic acid
636-61-3

D-Malic acid

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

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

Conditions
ConditionsYield
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%
D-Malic acid
636-61-3

D-Malic acid

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

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

(R)-3-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene for 8h; Reflux; optical yield given as %ee;90%
In m-xylene Reflux;78%
D-Malic acid
636-61-3

D-Malic acid

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

(R)-(+)-2-(2,5-difluorophenyl)pyrrolidine

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

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

Conditions
ConditionsYield
With triethylamine In ethanol at 20 - 65℃; Inert atmosphere;90%
D-Malic acid
636-61-3

D-Malic acid

eszopiclone
138729-47-2

eszopiclone

(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
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
ConditionsYield
In ethyl acetate for 18h;89%
ethanol
64-17-5

ethanol

D-Malic acid
636-61-3

D-Malic acid

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

(R)-2-Hydroxy-succinic acid 1-ethyl ester

Conditions
ConditionsYield
With salicylaldehyde at 80℃; for 14h; Inert atmosphere; chemoselective reaction;89%
D-Malic acid
636-61-3

D-Malic acid

zopiclon
43200-80-2

zopiclon

(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
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
ConditionsYield
In methanol; acetone at 10 - 48℃; for 4h;88%
In methanol; acetone at 55 - 56℃; for 0.5h; Product distribution / selectivity;41%
malic acid
617-48-1

malic acid

D-Malic acid
636-61-3

D-Malic acid

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

(R)-4-methyloxetan-2-one

Conditions
ConditionsYield
With hydrogenchloride; sodium borohydrid; lithium chloride In tetrahydrofuran; methanol88%
D-Malic acid
636-61-3

D-Malic acid

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

acetyl chloride
75-36-5

acetyl chloride

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

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

Conditions
ConditionsYield
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

636-61-3Relevant articles and documents

Racemic Structure and Optical Resolution by Preferential Crystallization of (+/-)-Organic Ammonium Hydrogen Malates

Shiraiwa, Tadashi,Sado, Yujin,Inoue, Mitsuo,Sakamoto, Keiji,Miyazaki, Hideya,Kurokawa, Hidemoto

, p. 899 - 904 (1988)

Gibbs energies of formation of racemate, binary melting point diagrams, and ternary solubility diagrams indicate that (+/-)-propylammonium ((+/-)-PA salt) and (+/-)-1,1,3,3-tetramethylbutylammonium ((+/-)-TMB salt) hydrogen malates are conglomerates at room temperature, whereas (+/-)-TMB salt forms a racemic compound at its melting point.Free energies of critical nucleation in supersaturated solutions were examined to resolve (+/-)-PA and -TMB salts efficiently by preferential crystallization.Successive preferential crystallization of (+/-)-PA salt in methanol at 10 deg C and that of (+/-)-TMB salt in water give (+)- and (-)-PA and -TMB salts with about 90percent optical purity.Optically pure (+)- and (-)-malic acids are obtained from purified (-)- and (+)-salts.

Sesquiterpene dimers esterified with diverse small organic acids from the seeds of Sarcandra glabra

Wang, Peng,Luo, Jun,Zhang, Yang-Mei,Kong, Ling-Yi

, p. 5362 - 5370 (2015/07/15)

11 new sesquiterpene dimers, sarglabolides A-K (1-11), and five known ones were isolated from the seeds of Sarcandra glabra. Their structures were elucidated by spectroscopic data analysis and chemical evidence. Sarglabolide A (1) was verified to exclusively possess a seventeen-membered macrocyclic ester ring formed by the scaffold of the sesquiterpene dimer and small organic acids, different from the eighteen-membered rings of the other reported analogues. The chiral small organic acid moieties were assigned to l-malic acid, d-malic acid, and d-tartaric acid based on the combination of spectroscopy, chemical derivatization and HPLC analysis. Dimers 1, 12 and 13 can significantly inhibit NO production in LPS-induced macrophages with IC50 values at 3.04, 4.65 and 2.33 μmol/L, respectively.

An approach to the chemotaxonomic differentiation of two European Dog's mercury species: Mercurialis annua L. and M. perennis L.

Lorenz, Peter,Duckstein, Sarina,Conrad, Juergen,Knoedler, Matthias,Meyer, Ulrich,Stintzing, Florian C.

experimental part, p. 282 - 297 (2012/05/04)

Mercurialis annua and M. perennis are medicinal plants used in complementary medicine. In the present work, analytical methods to allow a chemotaxonomic differentiation of M. annua and M. perennis by means of chemical marker compounds were established. In addition to previously published compounds, the exclusive presence of pyridine-3-carbonitrile and nicotinamide in CH2Cl2 extracts obtained from the herbal parts of M. annua was demonstrated by GC/MS. Notably, pyridine-3-carbonitrile was identified for the first time as a natural product. Further chromatographic separation of the CH2Cl2 extracts via polyamide yielded a MeOH fraction exhibiting a broad spectrum of side-chain saturated n-alkylresorcinols. While the n-alkylresorcinol pattern was similar for both plant species, some specific differences were observed for particular n-alkylresorcinol homologs. Finally, the investigation of H2O extracts by LC/MS/MS revealed the presence of depside constituents. Whereas, in M. perennis, a mixture of mercurialis acid (=(2R)-[(E)-caffeoyl]-2-oxoglutarate) and phaselic acid (=(E)-caffeoyl-2-malate) could be detected, in M. annua solely phaselic acid was found. By comparison with synthesized enantiomerically pure (2R)- and (2S)-phaselic acids, the configuration of the depside could be determined as (2S) in M. annua and as (2R) in M. perennis.

Process for preparing R-(-) -carnitine from S-(-)-chlorosuccinic acid or from a derivative thereof

-

Page column 9, (2008/06/13)

An inner salt of L-carnitine is prepared by reduction, with a suitable reducing agent, of a compound of formula (I): where X1and X2, which may be the same or different, are hydroxy, C1-C4alkoxy, phenoxy, halogen, or X1and X2, when taken together are an oxygen atom and the resulting compound is a derivative of succinic anhydride; Y is halogen, the mesyloxy or the tosyloxy group: and subsequent treatment with water, then with a base and then with trimethylamine.

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