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Merck
CN

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
Assay:
≥97.0% (T)

Key Documents

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Quality Level

200

functional group

hydroxyl, carboxylic acid

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.)

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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
BCCN6519
BCCM4184
BCCK3795
BCCF9122
BCCF5577

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Concise Total Synthesis of (-)-Erinapyrone B from D-(+)-Malic Acid
Samala R, et al.
Synthetic Communications, 44(4), 500-506 (2014)
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
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
K Leckel et al.
Clinical and experimental immunology, 134(2), 238-245 (2003-11-18)
Immunosuppression correlates with the development and recurrence of cancer. Mycophenolate mofetil (MMF) has been shown to reduce adhesion molecule expression and leucocyte recruitment into the donor organ. We have hypothesized that MMF might also prevent receptor-dependent tumour dissemination. Therefore, we
One pot green synthesis of α-aminophosphonates with D-Malic acid as an organocatalyst
AIP Conference Proceedings, 1860(1), 020057-020057 (2017)
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