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Merck

02300

D-(+)-Malic acid

unnatural form, ≥97.0% (T)

Synonym(s):

(R)-(+)-2-Hydroxysuccinic acid, D-Hydroxybutanedioic acid

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About This Item

Linear Formula:
HO2CCH2CH(OH)CO2H
CAS Number:
636-61-3
Molecular Weight:
134.09
UNSPSC Code:
51113400
NACRES:
NA.22
PubChem Substance ID:
329747411
EC Number:
211-262-2
Beilstein/REAXYS Number:
1723540
MDL number:
MFCD00004245

Key Documents

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Product Name

D-(+)-Malic acid, unnatural form, ≥97.0% (T)

InChI key

BJEPYKJPYRNKOW-UWTATZPHSA-N

InChI

1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1

SMILES string

O[C@H](CC(O)=O)C(O)=O

assay

≥97.0% (T)

optical activity

[α]20/D +28.0±2°, c = 5.5% in pyridine

quality

unnatural form

mp

98-102 °C (lit.)

functional group

carboxylic acid
hydroxyl

Quality Level

200

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Application

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.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF9122
BCCF5577
BCCD0398
BCCB0630
BCBR8459V

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One pot green synthesis of α-aminophosphonates with D-Malic acid as an organocatalyst
AIP Conference Proceedings, 1860(1), 020057-020057 (2017)
R Kaminsky et al.
Tropical medicine & international health : TM & IH, 1(2), 255-263 (1996-04-01)
The unique features of purine salvage systems of pathogenic haemoflagellates render them selectively susceptible to the cytotoxic effects of purine analogues. A series of acyclic nucleoside phosphonates were evaluated for activity against pathogenic haemoflagellates in vitro. One of the phosphonylmethoxyalkylpurines
Concise Total Synthesis of (-)-Erinapyrone B from D-(+)-Malic Acid
Samala R, et al.
Synthetic Communications, 44(4), 500-506 (2014)
M J Gómez-Lechón et al.
Hepatology (Baltimore, Md.), 23(5), 1012-1019 (1996-05-01)
Human hepatocytes stimulated with human recombinant hepatocyte growth factor (h-rHGF) (10 ng/mL) displayed a characteristic lag period before entering into the S phase. The duration of this delay was dependent on the timing of h-rHGF addition to cultures. The highest
C Orskov et al.
FEBS letters, 247(2), 193-196 (1989-04-24)
We developed specific, C-terminal radioimmunoassays for three proglucagon (PG) fragments: PG 151-158, PG 151-160 and PG 126-159 (glucagon-like peptide-2 (GLP-2] in order to determine the exact C-terminal sequence of the newly isolated GLP-2 in man and pig. The antigens and
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