AFCDB: 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

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

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

Showing 1 to 10 of 14 entries

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti atherosclerotic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti fibromyalgic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti seborrheic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti tubercular	33282	A substance that kills or slows the growth of bacteria.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
bacteristat	33282	A substance that kills or slows the growth of bacteria.	DUKE
bruchiphobe			DUKE

Showing 1 to 10 of 15 entries

Enzymes

Not Available

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Malic acid (FDB008114)

Structure for FDB008114 (Malic acid)