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27606

Sigma-Aldrich

DL-Malic acid

meets analytical specification of FCC, E296, 99-100.5% (alkalimetric)

Synonym(s):

(±)-2-Hydroxysuccinic acid, DL-Hydroxybutanedioic acid

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About This Item

Linear Formula:
HO2CCH2CH(OH)CO2H
CAS Number:
6915-15-7
Molecular Weight:
134.09
Beilstein/REAXYS Number:
1723539
EC Number:
230-022-8
MDL number:
MFCD00064212
UNSPSC Code:
12352106
PubChem Substance ID:
57648231
NACRES:
NA.25

vapor density

4.6 (vs air)

vapor pressure

<0.1 mmHg ( 20 °C)

assay

99-100.5% (alkalimetric)

form

solid

optical activity

[α]/D −0.10 to +0.10°

autoignition temp.

644 °F

quality

meets analytical specification of FCC, E296

technique(s)

IR spectroscopy: suitable

impurities

≤0.05% maleic acid
≤0.1% water insoluble matter
≤1% fumaric acid

ign. residue

≤0.1% (as SO4)

mp

129-133 °C
131-133 °C (lit.)

solubility

acetone: soluble 17.75 g/ 100 gm at 20 °C
diethyl ether: soluble 0.84 g/100 gm at 20 °C
dioxane: soluble 22.70 g/100 gm at 20 °C
ethanol: soluble 45.53 g/100 gm at 20 °C
methanol: soluble 82.70 g/100 g at 20 °C
water: soluble 55.8 g/100 gm at 20 °C
benzene: insoluble

cation traces

As: ≤3 mg/kg
Hg: ≤1 mg/kg
Pb: ≤2 mg/kg

suitability

complies for identity (IR)

application(s)

pharmaceutical (small molecule)

SMILES string

OC(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)

InChI key

BJEPYKJPYRNKOW-UHFFFAOYSA-N

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Application

DL-Malic acid is an organic acid used for studying the impact on ultrasound pasteurization. It has also been used to culture Pichia membraneafaciens.

Biochem/physiol Actions

Malic acid is a dicarboxylic acid and an important regulatory metabolite. It has been implicated in process of fruit ripening. Malic acid is important for the starch metabolism; low malic acid content results in transient accumulation of starch. Mitochondrial-malate metabolism modulates ADP-glucose pyrophosphorylase activity and redox status of plastids.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

397.4 °F

flash_point_c

203 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S Z Salleh-Mack et al.
Ultrasonics sonochemistry, 14(3), 323-329 (2006-09-13)
The objectives of this research were to study the effects of temperature, sugar concentration (8, 12, and 16 g/100ml), organic acids (citric and malic acids) and pH (2.5 and 4.0) on ultrasound pasteurization. The model organism used for the research
L-Malic acid production by polyacrylamide gel entrapped Pichia membranaefaciens.
Biotechnology Letters, 7, 329-334 (1985)
Danilo C Centeno et al.
The Plant cell, 23(1), 162-184 (2011-01-18)
Despite the fact that the organic acid content of a fruit is regarded as one of its most commercially important quality traits when assessed by the consumer, relatively little is known concerning the physiological importance of organic acid metabolism for
G Anneroth et al.
Scandinavian journal of dental research, 88(3), 214-218 (1980-06-01)
Two saliva stimulating drugs, solutions of Hybrin and malic acid were in an in vitro study found to have a heavy demineralizing effect on the root surface of the dental hard tissue. Consequently the drugs cannot be recommended to patients
Cuiyue Liang et al.
Plant physiology, 161(3), 1347-1361 (2013-01-24)
Low pH, aluminum (Al) toxicity, and low phosphorus (P) often coexist and are heterogeneously distributed in acid soils. To date, the underlying mechanisms of crop adaptation to these multiple factors on acid soils remain poorly understood. In this study, we
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