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Key Documents

02300

Sigma-Aldrich

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:
Molecular Weight:
134.09
Beilstein:
1723540
EC Number:
MDL number:
UNSPSC Code:
51113400
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

SMILES string

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

InChI

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

InChI key

BJEPYKJPYRNKOW-UWTATZPHSA-N

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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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Jian Yang et al.
Scientific reports, 8(1), 10253-10253 (2018-07-08)
Impactful dietary RNA delivery requires improving uptake and enhancing digestive stability. In mouse feeding regimes, we have demonstrated that a plant-based ribosomal RNA (rRNA), MIR2911, is more bioavailable than synthetic MIR2911 or canonical microRNAs (miRNAs). Here mutagenesis was used to
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)
Alexander Meyenberg et al.
Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie, 243(12), 1263-1271 (2005-05-24)
To evaluate the potential of the vitamin E compound alpha-tocotrienol as antifibrotic agent in vitro. Using human Tenon's capsule fibroblast cultures, the antiproliferative and cytotoxic effects of the different vitamin E forms alpha-tocopherol, alpha-tocopheryl acetate, alpha-tocopheryl succinate and alpha-tocotrienol were
Concise Total Synthesis of (-)-Erinapyrone B from D-(+)-Malic Acid
Samala R, et al.
Synthetic Communications, 44(4), 500-506 (2014)

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