Showing Compound Malic acid (FDB008114)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:56 UTC

Update date

2019-11-26 03:02:07 UTC

Primary ID

FDB008114

Secondary Accession Numbers

FDB007218

Chemical Information

FooDB Name

Malic acid

Description

Mainly used as an acidifier in a wide range of food, such as fruit drinks, jams, sweet and sour sauces, boiled sweets, chewing gum. Occasionally used as a metal ion chelator in wine or in hard water. Flavour enhancer Malic acid is the active ingredient in many sour or tart foods. Malic acid is found mostly in unripe fruits. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally. Malic acid is found in many foods, some of which are garden rhubarb, sour cherry, white lupine, and coconut.

CAS Number

6915-15-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Hydroxybutanedioic acid	ChEBI
2-Hydroxyethane-1,2-dicarboxylic acid	ChEBI
2-Hydroxysuccinic acid	ChEBI
alpha-Hydroxysuccinic acid	ChEBI
Aepfelsaeure	ChEBI
Apple acid	ChEBI
DL-Malic acid	ChEBI
e296	ChEBI
H2Mal	ChEBI
Hydroxybutanedioic acid	ChEBI
Hydroxysuccinic acid	ChEBI
Malate	Kegg
2-Hydroxybutanedioate	Generator
2-Hydroxyethane-1,2-dicarboxylate	Generator
2-Hydroxysuccinate	Generator
a-Hydroxysuccinate	Generator
a-Hydroxysuccinic acid	Generator
alpha-Hydroxysuccinate	Generator
Α-hydroxysuccinate	Generator
Α-hydroxysuccinic acid	Generator
DL-Malate	Generator
Hydroxybutanedioate	Generator
Hydroxysuccinate	Generator
Deoxytetrarate	HMDB
Deoxytetraric acid	HMDB
Musashi-NO-ringosan	HMDB
Pomalus acid	HMDB
R,S-Malate	HMDB
R,S-Malic acid	HMDB
R,SMalate	HMDB
R,SMalic acid	HMDB
Malic acid, disodium salt	HMDB
Malic acid, disodium salt, (R)-isomer	HMDB
Malic acid, disodium salt, (S)-isomer	HMDB
Malic acid, monopotassium salt, (+-)-isomer	HMDB
Malic acid, (R)-isomer	HMDB
Malic acid, calcium salt, (1:1), (S)-isomer	HMDB
Malic acid, magnesium salt (2:1)	HMDB
Calcium (hydroxy-1-malate) hexahydrate	HMDB
Malic acid, potassium salt, (R)-isomer	HMDB
Malic acid, sodium salt, (+-)-isomer	HMDB
2-Hydroxydicarboxylic acid	biospider
Butanedioic acid, 2-hydroxy-	biospider
Butanedioic acid, hydroxy-	biospider
E296	db_source
Hydroxy succinic acid	biospider
Hydroxyethane-1,2-dicarboxylic acid	biospider
Succinic acid, hydroxy-	biospider
α-hydroxysuccinate	Generator
α-hydroxysuccinic acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	218 g/L	ALOGPS
logP	-0.87	ALOGPS
logP	-1.1	ChemAxon
logS	0.21	ALOGPS
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	24.88 m³·mol⁻¹	ChemAxon
Polarizability	10.91 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H6O5

IUPAC name

2-hydroxybutanedioic acid

InChI Identifier

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

Isomeric SMILES

OC(CC(O)=O)C(O)=O

Average Molecular Weight

134.0874

Monoisotopic Molecular Weight

134.021523302

Classification

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Short-chain hydroxy acid
Beta-hydroxy acid
Fatty acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C4-dicarboxylic acid (CHEBI:6650 )
2-hydroxydicarboxylic acid (CHEBI:6650 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Fungi:

Aspergillus

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 35.83%; H 4.51%; O 59.66%	DFC
Melting Point	131-133 oC
Boiling Point	Not Available
Experimental Water Solubility	1000 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-1.26	HANSCH,C ET AL. (1995)
Experimental pKa	3.4
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0076-9000000000-ad60ea592282d09e4bd8	2015-03-01	View Spectrum
GC-MS	Maslic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0920000000-d3afa3ad5c227740eae3	Spectrum
GC-MS	Maslic acid, 3 TMS, GC-MS Spectrum	splash10-001i-0951000000-1d993823fa816ba3cfb1	Spectrum
GC-MS	Maslic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0930000000-6a116527910d172eb561	Spectrum
GC-MS	Maslic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0920000000-d3afa3ad5c227740eae3	Spectrum
GC-MS	Maslic acid, non-derivatized, GC-MS Spectrum	splash10-001i-0951000000-1d993823fa816ba3cfb1	Spectrum
Predicted GC-MS	Maslic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9100000000-aba7652c885a434930ef	Spectrum
Predicted GC-MS	Maslic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02j9-7191000000-b78c78194b39deee0ca4	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03e9-3900000000-6112a756a8c8c7c7cd50	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-9100000000-b3efe8bce2f89afcff34	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00ec-9300000000-c0aaa5301dcac30685db	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-7900000000-2a07c36db6acea9015af	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00rj-9200000000-316c7803efd1dfb76523	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9000000000-a442bcaaacb6f4eec14d	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-9800000000-03bfaee5de56f72ed927	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-9200000000-26a075efe73adc63a189	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-059f-9000000000-a3281a79477ac14e2eae	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

6650

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00744

CRC / DFC (Dictionary of Food Compounds) ID

DCG74-V:DCG74-V

EAFUS ID

2097

Dr. Duke ID

MALIC-ACID

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Malic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti-atherosclerotic	38070	An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti-fibromyalgic	52217	An agent that alleviates symptoms of fibromyalgia, reducing pain, fatigue, and inflammation. It plays a biological role in modulating neurotransmitter activity and immune response. Therapeutically, it's used to manage fibromyalgia, chronic pain, and fatigue, improving quality of life for patients with these conditions.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti-seborrheic	52217	An agent that reduces seborrheic dermatitis symptoms, commonly used in managing scalp and skin conditions, such as dandruff, itching, and flaking, by inhibiting fungal growth and inflammation.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-tubercular	33282	An agent that combats tuberculosis, playing a biological role in inhibiting the growth of Mycobacterium tuberculosis. Therapeutically, it is used to treat and prevent tuberculosis, with key medical applications including the treatment of active TB, latent TB, and TB meningitis, as well as preventing the spread of TB in high-risk populations.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Bacteristat	33282	An agent that inhibits bacterial growth, reducing the proliferation of microorganisms without killing them. Therapeutically, bacteristats are used to treat infections, preventing the spread of bacteria and allowing the host's immune system to clear the infection. Key medical uses include treating urinary tract infections, acne, and other bacterial infections where bactericidal agents may not be necessary.	DUKE
Bruchiphobe		An agent that counteracts Brucella bacteria, reducing infection risk. Therapeutically, it's used to prevent and treat brucellosis, a zoonotic disease. Key medical uses include prophylaxis and treatment of brucellosis in high-risk individuals, such as veterinarians and laboratory workers.	DUKE
Hemopoietic		An agent that stimulates the production of red blood cells, playing a crucial role in treating anemia, blood disorders, and supporting cancer patients undergoing chemotherapy, with key medical uses including increasing red blood cell count and improving oxygen delivery to tissues.	DUKE
Laxative	50503	An agent that stimulates bowel movements, relieving constipation by softening stool or increasing intestinal motility. Therapeutically, laxatives are used to treat constipation, prepare the bowel for medical procedures, and manage certain medical conditions, such as irritable bowel syndrome.	DUKE
Mycobactericide		An agent that kills bacteria of the genus Mycobacteria, playing a crucial role in treating mycobacterial infections. Therapeutically, it is used to combat tuberculosis, leprosy, and other related diseases, serving as a key medical tool in controlling and eliminating these infections.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Sialogogue		An agent that stimulates the flow of saliva, aiding digestion and oral health. Therapeutically, it helps manage dry mouth, protects teeth, and facilitates swallowing. Key medical uses include treating xerostomia, Sj�gren's syndrome, and radiation-induced salivary gland damage.	DUKE