ContaminantDB: Tartaric acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:20:13 UTC

Update Date

2016-10-28 10:03:21 UTC

Accession Number

CHEM003828

Identification

Common Name

Tartaric acid

Class

Small Molecule

Description

Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine. It is added to other foods to give a sour taste, and is used as an antioxidant. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death. The minimum recorded fatal dose for a human is about 12 grams. In spite of that, it is included in many foods, especially sour-tasting sweets. As a food additive, tartaric acid is used as an antioxidant with E number E334, tartrates are other additives serving as antioxidants or emulsifiers. Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images. It is a useful raw material in organic chemistry for the synthesis of other chiral molecules. The naturally occurring form of the acid is L-(+)-tartaric acid or dextrotartaric acid. The mirror-image (enantiomeric) form, levotartaric acid or D-(-)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially. Tartarate is believed to play a role in inhibiting kidney stone formation. Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract -- primarily in the large instestine. Only about 15-20% of consumed tartaric acid is secreted in the urine unchanged.

Contaminant Sources

Cosmetic Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens General
IARC Carcinogens Group 1
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Food Additive
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-(R,R)-Tartaric acid	ChEBI
(+)-L-Tartaric acid	ChEBI
(+)-Tartaric acid	ChEBI
(+)-Weinsaeure	ChEBI
(2R,3R)-2,3-Dihydroxybernsteinsaeure	ChEBI
(2R,3R)-2,3-Dihydroxysuccinic acid	ChEBI
(2R,3R)-Tartaric acid	ChEBI
(R,R)-(+)-Tartaric acid	ChEBI
(R,R)-Tartaric acid	ChEBI
L(+)-TARTARIC ACID	ChEBI
L-Threaric acid	ChEBI
Rechtsweinsaeure	ChEBI
Weinsteinsaeure	ChEBI
(R,R)-Tartrate	Kegg
L-Tartaric acid	Kegg
Tartrate	Kegg
2,3-Dihydroxybutanedioic acid	Kegg
(+)-(R,R)-Tartarate	Generator
(+)-L-Tartarate	Generator
(+)-Tartarate	Generator
(2R,3R)-2,3-Dihydroxysuccinate	Generator
(2R,3R)-Tartarate	Generator
(R,R)-(+)-Tartarate	Generator
(R,R)-Tartarate	Generator
L(+)-TARTARate	Generator
L-Threarate	Generator
(R,R)-Tartric acid	Generator
L-Tartarate	Generator
Tartric acid	Generator
2,3-Dihydroxybutanedioate	Generator
Tartarate	Generator
Aluminum tartrate	HMDB
Ammonium tartrate	HMDB
Potassium tartrate	HMDB
Seignette salt	HMDB
Sodium ammonium tartrate	HMDB
Stannous tartrate	HMDB
Tartaric acid, calcium salt, (R-r,r)-isomer	HMDB
Calcium tartrate tetrahydrate	HMDB
Sodium tartrate	HMDB
Tartaric acid, ((r,r)-(+-))-isomer	HMDB
Tartaric acid, monoammonium salt, (R-(r,r))-isomer	HMDB
(R,r)-(+-)-2,3-dihydroxybutanedioic acid, monoammonium monosodium salt	HMDB
MN(III) tartrate	HMDB
Calcium tartrate	HMDB
Tartaric acid, (R-(r,r))-isomer	HMDB
Sodium potassium tartrate	HMDB
Tartaric acid, (r,s)-isomer	HMDB
Tartaric acid, (S-(r,r))-isomer	HMDB
Tartaric acid, ammonium sodium salt, (1:1:1) salt, (r,r)-(+-)-isomer	HMDB
(+)-(2R,3R)-Tartaric acid	HMDB
(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid	HMDB
(2R,3R)-2,3-Dihydroxybutanedioate	HMDB
(2R,3R)-2,3-Dihydroxybutanedioic acid	HMDB
(2R,3R)-2,3-Tartaric acid	HMDB
1,2-Dihydroxyethane-1,2-dicarboxylic acid	HMDB
2,3-Dihydroxy-succinate	HMDB
2,3-Dihydroxy-succinic acid	HMDB
2,3-Dihydroxysuccinic acid	HMDB
D-a,b-Dihydroxysuccinic acid	HMDB
D-Tartaric acid	HMDB
Dextrotartaric acid	HMDB
L-(+)-Tartaric acid	HMDB
Natural tartaric acid	HMDB
TAR	HMDB
Threaric acid	HMDB
TLA	HMDB
Weinsaeure	HMDB
(2R,3R)-(+)-Tartaric acid	HMDB
Dihydroxysuccinic acid	HMDB
Tartaric acid	HMDB

Chemical Formula

C₄H₆O₆

Average Molecular Mass

150.087 g/mol

Monoisotopic Mass

150.016 g/mol

CAS Registry Number

87-69-4

IUPAC Name

(2R,3R)-2,3-dihydroxybutanedioic acid

Traditional Name

L(+)-tartaric acid

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1

InChI Key

FEWJPZIEWOKRBE-JCYAYHJZSA-N

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

tartaric acid (CHEBI:15671 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Platelet
Prostate

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	169 °C
Boiling Point	Not Available
Solubility	582 mg/mL at 20 °C

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	11.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0930000000-19235937e21066a9c484	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-000f-0961000000-559c31b016f4fb3700d2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-0961000000-1b17d674621eb9d88c3c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0930000000-19235937e21066a9c484	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000f-0961000000-559c31b016f4fb3700d2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9200000000-df0ce9fba754b55674b1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000b-7900000000-d247ec12b77f427e9a76	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-05fu-9000000000-4bf01ad116d24a453817	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-4da65da10f3a34f77688	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-ecb902731b9f6eb3764d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0072-9700000000-1e8e6f410c1d71af856e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-f13ad2560d3e6818db9c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-05fu-9000000000-f46a01eb933ba6fbceac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-08dec35ca6a80add253a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-ecb902731b9f6eb3764d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0072-9700000000-1e8e6f410c1d71af856e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-f13ad2560d3e6818db9c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-05fu-9000000000-f46a01eb933ba6fbceac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-08dec35ca6a80add253a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-05fu-9000000000-2bc9b64b80733677dbe6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e65d82322cd0037aa733	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0072-9600000000-0276f4093011ce886f64	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-007a-9300000000-5ad0de9efcf7b25ff3dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-1900000000-6a73140cfa5a0c0234e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9600000000-ca8758d1e65f5dbe35d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a70-9100000000-1630b812321816f95d11	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05bb-7900000000-146a1c7b189a7bbacda0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9500000000-f7af07684007cf14bdce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a8f5502da9e4d13e4144	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4s-4900000000-4b81a8a41abed679d134	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9200000000-b73e0df104053da76268	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9000000000-16517a02beb9427ceaff	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum