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Safety Information

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:
636-61-3
Molecular Weight:
134.09
Beilstein:
1723540
EC Number:
211-262-2
MDL number:
MFCD00004245
UNSPSC Code:
51113400
PubChem Substance ID:
329747411
NACRES:
NA.22

Quality Level

200

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

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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

02300-25G:
02300-VAR:
02300-5G:
02300-BULK:
02300-1G:

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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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