L-(-)-Malic acid

Names

[ CAS No. ]:
97-67-6

[ Name ]:
L-(-)-Malic acid

[Synonym ]:
hydroxy-butanedioic acid
(S)-2-hydroxysuccinic acid
Butanedioic acid, 2-hydroxy-
Hydroxybutandisaeure
MALIC ACID, (DL)
EINECS 202-601-5
2-hydroxybutane-1,4-dioic acid
Malic acid
Malic acid, dl-
DL-MALIC ACID
MFCD00064213
2-Hydroxy-succinic acid
DL-Hydroxybutanedioic acid
L(-)-Malic Acid
R,S(±)-Malic acid
Butanedioic acid, hydroxy-
alpha-Hydroxysuccinic acid
(±)-1-Hydroxy-1,2-ethanedicarboxylic Acid
UNII:817L1N4CKP
alpha-hydroxysuccinicacid
hydroxysuccinic acid
DL(+/-)-MALIC ACID
R,S-Malic acid
2-hydroxybutanedioic acid
2-Hydroxysuccinic Acid
a-Hydroxysuccinic Acid
(±)-Malic Acid
L-Malic acid

Biological Activity

[Description]:

(S)-2-Hydroxysuccinic acid is a dicarboxylic acid in naturally occurring form, contributes to the pleasantly sour taste of fruits and is used as a food additive.

[Related Catalog]:

Natural Products >> Acids and Aldehydes

Research Areas >> Metabolic Disease

[Target]

Human Endogenous Metabolite

[In Vitro]

It is showed that ME is essential for (S)-2-Hydroxysuccinic acid (L-malic acid) utilization in L. casei. Furthermore, deletion of either the gene encoding the histidine kinase or the response regulator of the TC system resulted in the loss of the ability to grow on (S)-2-Hydroxysuccinic acid, thus indicating that the cognate TC system regulates and is essential for the expression of ME. Transcriptional analyses shows that expression of maeE is induced in the presence of (S)-2-Hydroxysuccinic acid and repressed by glucose, whereas TC system expression is induced by (S)-2-Hydroxysuccinic acid and is not repressed by glucose[1].

[References]

[1]. Landete JM, et al. Requirement of the Lactobacillus casei MaeKR two-component system for L-malic acid utilization via a malic enzyme pathway. Appl Environ Microbiol. 2010 Jan;76(1):84-95.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
306.4±27.0 °C at 760 mmHg

[ Melting Point ]:
101-103 °C(lit.)

[ Molecular Formula ]:
C₄H₆O₅

[ Molecular Weight ]:
134.087

[ Flash Point ]:
153.4±20.2 °C

[ Exact Mass ]:
134.021530

[ PSA ]:
94.83000

[ LogP ]:
-1.26

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.529

[ Water Solubility ]:
soluble

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
ON7175000

[ HS Code ]:
2918199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918199090

[ Summary ]:
2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

Articles

Physiology and pathophysiology of organic acids in cerebrospinal fluid.

J. Inherit. Metab. Dis. 16(4) , 648-69, (1993)

Concentrations of organic acids in cerebrospinal fluid (CSF) appear to be directly dependent upon their rate of production in the brain. There is evidence that the net release of short-chain monocarbo...

Age-related reference values for urinary organic acids in a healthy Turkish pediatric population.

Clin. Chem. 40(6) , 862-6, (1994)

Organic acid concentrations were quantified by gas chromatography and the individual acids identified by mass spectrometry in urine specimens from a healthy Turkish pediatric population of ages 2 days...

Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression.

Nature 457(7231) , 910-4, (2009)

Multiple, complex molecular events characterize cancer development and progression. Deciphering the molecular networks that distinguish organ-confined disease from metastatic disease may lead to the i...