Tartaric acid

Identification

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Name
L-tartaric acid
Commonly known or available as Tartaric acid
Accession Number
DB09459
Type
Small Molecule
Groups
Experimental
Description

Tartaric acid is a white crystalline organic acid that occurs naturally in many plants, most notably in grapes.Tartaric is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

Structure
Thumb
Synonyms
  • (+)-(R,R)-tartaric acid
  • (+)-L-tartaric acid
  • (+)-Tartaric acid
  • (+)-Weinsäure
  • (2R,3R)-2,3-Dihydroxybernsteinsäure
  • (2R,3R)-2,3-dihydroxysuccinic acid
  • (2R,3R)-Tartaric acid
  • (R,R)-(+)-tartaric acid
  • (R,R)-Tartaric acid
  • ácido tartárico
  • L-threaric acid
  • Rechtsweinsäure
  • Tartaric acid
  • Weinsteinsäure
External IDs
E 334 / E-334 / FEMA NO. 3044 / INS NO.334 / INS-334 / NSC-62778
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Baros Effervescent GranulesL-tartaric acid (420 mg) + Sodium bicarbonate (460 mg)Granule, effervescentOralTyco Healthcare1988-12-312010-01-07Canada
BicaruvasL-tartaric acid (2 g/944mL) + Calcium carbonate (1 g/944mL) + Citric acid monohydrate (15 g/944mL) + Sodium bicarbonate (19 g/944mL)Powder, for solutionOralProsana Distribuciones, S.A. De C.V.2013-04-23Not applicableUs
BicaruvasL-tartaric acid (2 g/944mL) + Calcium carbonate (1 g/944mL) + Citric acid monohydrate (15 g/944mL) + Sodium bicarbonate (19 g/944mL)Powder, for solutionOralProsana Distribuciones, S.A. De C.V.2013-04-23Not applicableUs
BicaruvasL-tartaric acid (220 mg/118mL) + Calcium carbonate (50 mg/118mL) + Citric acid monohydrate (1827 mg/118mL) + Sodium bicarbonate (2452 mg/118mL)Powder, for solutionOralProsana Distribuciones, S.A. De C.V.2013-04-23Not applicableUs
Brioschi Childrens Effervescent AntacidL-tartaric acid (1.05 g/4g) + Sodium bicarbonate (1.17 g/4g)Granule, effervescentOralBrioschi, Inc.2011-04-272016-03-25Us
Brioschi Effervescent AntacidL-tartaric acid (1.63 g/6g) + Sodium bicarbonate (1.8 g/6g)Granule, effervescentOralBrioschi, Inc.2010-09-202016-03-25Us
E-Z-gas 2 GranulesL-tartaric acid (1.648 g) + Sodium bicarbonate (1.808 g)PowderOralTherapex Division De E Z Em Canada Inc1985-12-312000-04-13Canada
Gingera Effervescent AntacidL-tartaric acid (1.62 g/6g) + Sodium bicarbonate (1.8 g/6g)Granule, effervescentOralBrioschi, Inc.2011-04-292016-03-25Us
Unik Zoru PwrL-tartaric acid (1.05 g) + Sodium bicarbonate (1.05 g)PowderOralTherapex Division De E Z Em Canada Inc1981-12-312000-08-01Canada
Unik Zoru TabL-tartaric acid (52.5 mg) + Sodium bicarbonate (52.5 mg)TabletOralTherapex Division De E Z Em Canada Inc1981-12-312004-06-10Canada
Categories
UNII
W4888I119H
CAS number
87-69-4
Weight
Average: 150.0868
Monoisotopic: 150.016437924
Chemical Formula
C4H6O6
InChI Key
FEWJPZIEWOKRBE-JCYAYHJZSA-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)/t1-,2-/m1/s1
IUPAC Name
(2R,3R)-2,3-dihydroxybutanedioic acid
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O

Pharmacology

Indication

Tartaric Acid is primarily indicated in conditions like Antiscorbutic, Antiseptic.

Associated Conditions
Pharmacodynamics

Tartaric acid is used to generate carbon dioxide through interaction with sodium bicarbonate following oral administration. Carbon dioxide extends the stomach and provides a negative contrast medium during double contrast radiography. In high doses, this agent acts as a muscle toxin by inhibiting the production of malic acid, which could cause paralysis and maybe death.

Mechanism of action
Not Available
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Oral or parenteral doses of monosodium 14C-L(+)-tartrate (400 mg/kg) are rapidly excreted by rats and a proportion completely metabolized to CO2. The oral dose was well-absorbed.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract , primarily in the large instestine.

Route of elimination

Only about 15-20% of consumed tartaric acid is secreted in the urine unchanged.

Half life
Not Available
Clearance
Not Available
Toxicity

Routes of Entry: Inhalation. Ingestion.

Toxicity to Animals: Lowest Published Lethal Dose: LDL [Rat - Route: oral; Dose: 7500 mg/kg LDL Rabbit - Route: Oral; Dose: 5000 mg/kg LDL [Dog] - Rout: Oral; Dose: 5000 mg/kg Lethal Dose/Conc 50% kill: LD50 [Mouse] - Route: Intravenous; Dose: 485 mg/kg

Other Toxic Effects on Humans: Acute Potential Health Effects: Skin: Causes skin irritation Eyes: Causes eye irritation Inhalation: Causes respiratory tract irritation Ingestion: Causes gastrointestinal tract irritation with nausea, vomiting and diarrhea. May affect kidneys (kidney damage), blood, and behavior (convulsions, somnolence), and respiration. Chronic Potential Health Effects: Ingestion: Repeated or prolonged ingestion may cause lesions of the mouth, gastric ulcers, gastrointestinal hyperacidity, and symptoms similar to those of metal fume fever - flu-like condition with fever, chills, sweats, nausea, vomiting, muscle aches, pains, and weakness. Skin: Repeated or prolonged skin contact may cause skin ulcerations or lesions.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe excretion of 2,5-Dimethoxy-4-ethylamphetamine can be decreased when combined with L-tartaric acid.
2,5-Dimethoxy-4-ethylthioamphetamineThe excretion of 2,5-Dimethoxy-4-ethylthioamphetamine can be decreased when combined with L-tartaric acid.
4-Bromo-2,5-dimethoxyamphetamineThe excretion of 4-Bromo-2,5-dimethoxyamphetamine can be decreased when combined with L-tartaric acid.
AmphetamineThe excretion of Amphetamine can be decreased when combined with L-tartaric acid.
BenzphetamineThe excretion of Benzphetamine can be decreased when combined with L-tartaric acid.
ChlorphentermineThe excretion of Chlorphentermine can be decreased when combined with L-tartaric acid.
ClomocyclineThe therapeutic efficacy of Clomocycline can be decreased when used in combination with L-tartaric acid.
DemeclocyclineThe therapeutic efficacy of Demeclocycline can be decreased when used in combination with L-tartaric acid.
DextroamphetamineThe excretion of Dextroamphetamine can be decreased when combined with L-tartaric acid.
DiethylpropionThe excretion of Diethylpropion can be decreased when combined with L-tartaric acid.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
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Food Interactions
Not Available

References

General References
  1. Chasseaud LF, Down WH, Kirkpatrick D: Absorption and biotransformation of L(+)-tartaric acid in rats. Experientia. 1977 Aug 15;33(8):998-9. [PubMed:891842]
  2. Pubchem [Link]
  3. Wikipedia [Link]
External Links
Human Metabolome Database
HMDB00956
PubChem Compound
444305
PubChem Substance
347827854
ChemSpider
392277
ChEBI
15671
ChEMBL
CHEMBL1236315
HET
TLA
Wikipedia
Tartaric_acid
PDB Entries
1alu / 1d5r / 1d6j / 1ei6 / 1eks / 1fs5 / 1gu1 / 1h3d / 1j2z / 1k2y
show 403 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Granule, effervescentOral
Powder, for solutionOral
PowderOral
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility161.0 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.8ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.21 m3·mol-1ChemAxon
Polarizability11.33 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0930000000-19235937e21066a9c484
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-000f-0961000000-559c31b016f4fb3700d2
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0007-0961000000-1b17d674621eb9d88c3c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0930000000-19235937e21066a9c484
GC-MS Spectrum - GC-MSGC-MSsplash10-000f-0961000000-559c31b016f4fb3700d2
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-000b-7900000000-d247ec12b77f427e9a76
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-05fu-9000000000-4bf01ad116d24a453817
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0006-9000000000-4da65da10f3a34f77688
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0002-0900000000-ecb902731b9f6eb3764d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0072-9700000000-1e8e6f410c1d71af856e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00di-9000000000-f13ad2560d3e6818db9c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-05fu-9000000000-f46a01eb933ba6fbceac
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-08dec35ca6a80add253a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-ecb902731b9f6eb3764d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0072-9700000000-1e8e6f410c1d71af856e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-f13ad2560d3e6818db9c
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-05fu-9000000000-f46a01eb933ba6fbceac
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-08dec35ca6a80add253a
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as sugar acids and derivatives. These 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
Short-chain hydroxy acids and derivatives / Beta hydroxy acids and derivatives / Monosaccharides / Fatty acids and conjugates / Dicarboxylic acids and derivatives / Alpha hydroxy acids and derivatives / Secondary alcohols / 1,2-diols / Carboxylic acids / Organic oxides
show 2 more
Substituents
Beta-hydroxy acid / Short-chain hydroxy acid / Sugar acid / Monosaccharide / Hydroxy acid / Dicarboxylic acid or derivatives / Alpha-hydroxy acid / Fatty acid / Secondary alcohol / 1,2-diol
show 7 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
tartaric acid (CHEBI:15671)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Catalytic activity
General Function
Udp-galactose:beta-n-acetylglucosamine beta-1,3-galactosyltransferase activity
Specific Function
Involved in the biosynthesis of L2/HNK-1 carbohydrate epitope on glycoproteins. Can also play a role in glycosaminoglycan biosynthesis. Substrates include asialo-orosomucoid (ASOR), asialo-fetuin, ...
Gene Name
B3GAT1
Uniprot ID
Q9P2W7
Uniprot Name
Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1
Molecular Weight
38255.675 Da
References
  1. UniProt [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Catalytic activity
General Function
Zinc ion binding
Specific Function
Hydroxylates HIF-1 alpha at 'Asp-803' in the C-terminal transactivation domain (CAD). Functions as an oxygen sensor and, under normoxic conditions, the hydroxylation prevents interaction of HIF-1 w...
Gene Name
HIF1AN
Uniprot ID
Q9NWT6
Uniprot Name
Hypoxia-inducible factor 1-alpha inhibitor
Molecular Weight
40285.25 Da
References
  1. UniProt [Link]
  2. HMDB [Link]

Drug created on November 30, 2015 12:10 / Updated on August 02, 2019 08:43