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Record Information

Version

2.0

Creation Date

2012-05-31 14:31:20 -0600

Update Date

2015-06-03 17:19:27 -0600

Secondary Accession Numbers

ECMDB20172

Identification

Name:

Meso-Tartaric acid

Description

Meso-tartaric acid is a member of the chemical class known as Dicarboxylic Acids and Derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2R,3S)-2,3-dihydroxybutanedioate
(2R,3S)-2,3-dihydroxybutanedioic acid
(2R,3S)-2,3-dihydroxysuccinate
(2R,3S)-2,3-dihydroxysuccinic acid
(2R,3S)-rel-2,3-dihydroxybutanedioate
(2R,3S)-rel-2,3-dihydroxybutanedioic acid
(2R,3S)-tartarate
(2R,3S)-tartaric acid
(R*,S*)-2,3-dihydroxybutanedioate
(R*,S*)-2,3-dihydroxybutanedioic acid
1,4-BUTANEDIOate,2,3-dihydroxy (tartarate)
1,4-BUTANEDIOIC ACID,2,3-DIHYDROXY (TARTARIC ACID)
2,3-Dihydroxy-(R*,S*)-Butanedioate
2,3-Dihydroxy-(R*,S*)-Butanedioic acid
2,3-Dihydroxy-Butanedioate
2,3-Dihydroxy-Butanedioic acid
2,3-Dihydroxysuccinate
2,3-Dihydroxysuccinic acid
meso-tartaric acid
Erythrarate
Erythraric acid
Internally compensate tartarate
Internally compensate tartaric acid
Internally compensated tartarate
Internally compensated tartaric acid
Internally compensic acid tartaric acid
M-Tartarate
M-Tartaric acid
Meso-Tartarate
Meso-tartarate monohydrate
Meso-tartaric acid monohydrate
Meso-tartaric acid monohydric acid
Meso-tartrate
Meso-tartric acid
Mesotartarate
Mesotartaric acid
Mesoweinsaeure
S,R Meso-tartarate
S,R Meso-tartaric acid
SRT
Unresolvable tartarate
Unresolvable tartaric acid

Chemical Formula:

C₄H₆O₆

Weight:

Average: 150.0868
Monoisotopic: 150.016437924

InChI Key:

FEWJPZIEWOKRBE-UHFFFAOYSA-N

InChI:

InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)

CAS number:

147-73-9

IUPAC Name:

2,3-dihydroxybutanedioic acid

Traditional IUPAC Name:

(.+-.)-tartaric acid

SMILES:

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Sugar acid
Short-chain hydroxy acid
Beta-hydroxy acid
Fatty acid
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Secondary alcohol
1,2-diol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetraric acid (CHEBI:15674 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

147 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	560 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	161 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-1.8	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.21 m³·mol⁻¹	ChemAxon
Polarizability	11.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Meso-Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ion

SMPDB Pathways:

Not Available

KEGG Pathways:

Glyoxylate and dicarboxylate metabolism ec00630

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-473bf90ce56c0c0592a0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-473bf90ce56c0c0592a0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-473bf90ce56c0c0592a0	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-473bf90ce56c0c0592a0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9200000000-df0ce9fba754b55674b1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-00di-8029100000-283552abf9161a349136	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-5900000000-4c66eac9e5850c5fcbe4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0072-9600000000-17c4d1ba2b96cd7ef84c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0072-9600000000-f9fb12efb15f5ed29bce	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0072-9600000000-4115648caec12719bc40	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00du-9000000000-76ecadb353351b98d37d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-1900000000-81029c7f5a1a1f6c7eef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9500000000-0540950c816c3054bc75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a70-9100000000-ab88b0c77d915bdf94c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05bb-8900000000-6145a4d3d74ad91e7c08	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9500000000-e810b360131a0cd0626c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-fd760c42934208e53eab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05o0-3900000000-e52d00e2e7427df264f9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05p9-9300000000-1e180faafcb2fce14102	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bt9-9000000000-254ae2874ffc06d5337a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4s-4900000000-4b81a8a41abed679d134	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9200000000-b73e0df104053da76268	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-4d8ce26149e6d7a8763f	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9000000000-16517a02beb9427ceaff	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15673
HMDB ID	HMDB0059916
Pubchem Compound ID	447315
Kegg ID	C00552
ChemSpider ID	852
Wikipedia ID	Tartaric_Acid
BioCyc ID	MESO-TARTRATE
EcoCyc ID	MESO-TARTRATE

Enzymes

Protein Details

1. D-malate dehydrogenase [decarboxylating]

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the NAD(+)-dependent oxidative decarboxylation of D-malate into pyruvate. Is essential for aerobic growth on D- malate as the sole carbon source. But is not required for anaerobic D-malate utilization, although DmlA is expressed and active in those conditions. Appears to be not able to use L- tartrate as a substrate for dehydrogenation instead of D-malate
Gene Name:: dmlA
Uniprot ID:: P76251
Molecular weight:: 40315

Reactions

(R)-malate + NAD(+) = pyruvate + CO(2) + NADH.

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Meso-Tartaric acid (M2MDB001019)

Structure for #<Compound:0xabf5afa4>

Enzymes

Reactions