Basic information
- Standard SMILES
O=C(O)[C@@H](O)[C@@H](O)C(=O)O- InChIKey
FEWJPZIEWOKRBE-XIXRPRMCSA-N- Molecular formula
- C4H6O6
- Average molar mass
- 150.09 g/mol
- Monoisotopic mass
- 150.01643791
Overview
Meso-tartaric acid is a 2,3-dihydroxybutanedioic acid that has meso configuration. It is a conjugate acid of a meso-tartrate(1-).
Names & identifiers
- Preferred name
- Meso-Tartaric acid
- IUPAC
- (2R,3S)-2,3-dihydroxybutanedioic acid
- English name
- DL-Tartaric acid
- Molecular formula
- C4H6O6
- Molecular weight
- 150.09
Names & synonyms
mesotartaric acidmeso-tartaric acid147-73-9erythraric acid(2R,3S)-2,3-dihydroxybutanedioic acidi-Tartaric acid(r,s)-tartaric acid(2R,3S)-tartaric acidm-tartaric acid(2R,3S)-2,3-dihydroxysuccinic acidTartaric acid, meso-(R*,S*)-2,3-Dihydroxybutanedioic acid
Show more names
TARTARIC ACIDRACEMIC ACIDdl-Tartaric acid anhydrousDL-TARTRATEDL-TartaricClopidogrel Impurity 45DL-Tartaric acid concentrateButanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-DL-Tartaric acid 133-37-9 pure 99% food additives Paratartaric acid kf-wang(at)kf-chem.comUvic acid
JQO211TF1ACHEBI:15673DTXSID60883336RefChem:156674GlyTouCan:G12655FYDTXCID501774085G12655FY205-696-1
Database identifiers
- CAS
133-37-9、147-73-9、5990-63-6- PubChem CID
- 447315
- DTXSID
DTXSID60883336- ChEMBL
CHEMBL225983- ChEBI
CHEBI:15673- UNII
- JQO211TF1A
- EC Number
- 205-105-7、205-696-1、629-249-9
- Nikkaji
- J134.706C
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 115 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 134
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Organic Acids
SpringerMaterials PropertiesCrystal structure
FragrancesFragrance Ingredient (Tartaric acid (d-, l-, dl-, meso-)) -> IFRA transparency List
LogP-0.76 (calculated)
DensityRelative density (water = 1): 1.79
Flavoring AgentsEU Flavoring substances
SolubilitySolubility in water, g/l at 20 °C: 1400 (very soluble)
Flash Point210 °C c.c.
Melting Point206 °C
Physical Description
Dry Powder
White solid; [ICSC] Colorless or white odorless solid; [JECFA] White odorless crystalline powder; [Acros Organics MSDS]
WHITE CRYSTALLINE POWDER.
Collision Cross Section
120.87 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
118.4 Ų [M-H]-
Autoignition Temperature425 °C
Physicochemical properties
- Melting point
- 210 · 210-212 °C(lit.)
- Boiling point
- 191.59 °C · 191.59°C (rough estimate)
- alpha
- 20 · [α]D20 -0.2～+0.2° (c=20, H2O)
- Density
- 1.788 · 1.788
- vapor pressure
- 0.1 hPa · <0.1 hPa (20 °C)
- FEMA
- 3044 · 3044 | TARTARIC ACID (D-, L-, DL-, MESO-)
- refractive index
- 1.586 · 1.5860 (estimate)
- FLAVIS Number
- 8.018 · 08.018 | Tartaric acid
- Flash point
- 210 °C · 210 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 2 O: · H2O: 0.1 g/mL, clear
- form
- Liquid
- pka
- 3.03 · 3.03, 4.37(at 25℃)
- color
- White
- PH
- 3.19 · 3.19(1 mM solution);2.58(10 mM solution);2.03(100 mM solution);
- Odor
- 100 % · at 100.00 %. very mild caramellic
- Odor Type
- odorless
- biological source
- synthetic
- Water Solubility
- soluble
- Merck
- 14 · 14,9069
- JECFA Number
- 621 · 621
- BRN
- 1725148 · 1725148
- Dielectric constant
- 35.9 · 35.9(-10℃)
- Stability
- Stable. Incompatible with bases, oxidizing agents, reducing agents, silver.
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- BUFFERINGFRAGRANCE
- 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-/m0/s1
- InChIKey
- FEWJPZIEWOKRBE-UHFFFAOYSA-N
- SMILES
- O[C@@H]([C@H](O)C(O)=O)C(O)=O
- LogP
- -1.43 · -1.43
- CAS DataBase Reference
- 133 · 133-37-9(CAS DataBase Reference)
- FDA UNII
- 4 J4Z8788N8 · 4J4Z8788N8
- NIST Chemistry Reference
- Tartaric acid(133-37-9)
- EPA Substance Registry System
- 2 · Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel- (133-37-9)
- UNSPSC Code
- 41116105 · 41116105
- NACRES
- 21 · NB.21
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 318 · H318
- Precautionary statements
- 280 · P280-P305+P351+P338+P310
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-41
- Safety Statements
- 26 · 26-37/39-36
- WGK Germany
- 3 · 3
- Autoignition Temperature
- 425 °C · 425 °C
- TSCA
- TSCA listed
- HS Code
- 29181200 · 29181200
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 · Eye Dam. 1
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 5.1% (26 of 506) of reports.
Danger
H315 (22.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 506 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Hazard information
Regulatory Information
Chemical: Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(.+-.)-
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 03-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34095
DL-Tartaric acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(.+-.)-: Human health tier I assessment
Fire HazardsCombustible.
Hazards SummaryCauses burns; Inhalation of aerosol may cause pulmonary edema; [ICSC] An irritant; [Acros Organics MSDS]
Chemical DangersThe solution in water is a medium strong acid. Reacts with fluorine, strong oxidants, hydrogen peroxide, alkaline compounds and silver. This produces toxic fumes.
Physical DangersThe vapour is heavier than air.
Hazard Classes and Categories
Skin Irrit. 2 (22.1%)
Skin Irrit. 2 (50%)
Skin Irrit. 2 (100%)
Safety & protection
Fire FightingUse water spray, powder, foam, carbon dioxide.
First Aid Measures
Fresh air, rest. Seek medical attention if you feel unwell.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.
Rinse mouth. Give one or two glasses of water to drink. Seek medical attention if you feel unwell.
Safe StorageStore only in original packaging.
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Store and dispose of according to local regulations.
Eye PreventionWear safety goggles.
Fire PreventionNO open flames.
Inhalation RiskA harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT DISPERSION OF DUST! STRICT HYGIENE!
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse local exhaust, ventilation or breathing protection.
Effects of Short Term ExposureThe substance is corrosive to the eyes. The substance is irritating to the skin and upper respiratory tract.
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms
Cough. Sore throat. Burning sensation.
Redness.
Redness. Pain. Severe burns.
Cough. Sore throat. Burning sensation. Nausea. Vomiting.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29181200
- risk_code
- 36/37/38-41
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- safety_code
- 26-37/39-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H318
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1
- Autoignition Temperature
- 425 °C
- Precautionary statements
- P280-P305+P351+P338+P310
Chemistry & industry
Uses & manufacturing
UsesUsed as a synergist for antioxidants, acid, emulsifier, sequestrant, and flavoring agent; [JECFA]
U.S. Production2023: 43,652 lb
Industry UsesNot Known or Reasonably Ascertainable
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENTFood Additives -> ACID; ANTIOXIDANT_SYNERGIST; EMULSIFIER; SEQUESTRANT; SYNERGIST -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENTFood Additives -> ACID; ANTIOXIDANT_SYNERGIST; EMULSIFIER; SEQUESTRANT; SYNERGIST -> JECFA Functional Classes
General Manufacturing Information
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-: ACTIVE
Butanedioic acid, 2,3-dihydroxy-, (2R,3S)-rel-: ACTIVE
Applications
Occurrenced-Tartaric acid occurs in many fruits or other parts of the plant, free or combined with potassium, calcium or magnesium. It is also reported found in raw, lean fish, white wine, red wine and port wine.
UsesDL-Tartaric acid is used as a synergist for antioxidants, emulsifier, sequestrant and flavoring agent. It is also added with citric acid to prepare effervescent salts, thereby enhancing the taste of oral medications. It is also utilized in pigments, processing aids, ink, toner and colorant products. It acts as a chelating agent in metal and farming industries. Further, it is used as lubricant and grease. It is mixed with sodium bicarbonate and used as a leavening agent in food preparation. In the pharmaceutical industry, it is utilized in the preparation of tartar emetic, which is used in cough syrup as an expectorant.
Preparation methods
PreparationThe tartrates used in commerce are obtained as a by-product of wine manufacture and have the L(+) configuration. Produced from argols or wine lees, which are formed in the manufacture of wine by extracting the potassium acid tartrate, transforming this into the calcium salt and then acidifying with dilute sulfuric acid; also by oxidation of d-glucose with nitric acid. The dl-tartaric acid is obtained by boiling the d-tartaric acid with an aqueous solution of NaOH or by oxidation of fumaric acid. The l- and the meso-tartaric acid are also known, but are less important.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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Additional notes
DefinitionChEBI: DL-Tartaric acid is a tetraric acid that is butanedioic acid substituted by hydroxy groups at positions 2 and 3. It has a role as a human xenobiotic metabolite and a plant metabolite. It is a conjugate acid of a 3-carboxy-2,3-dihydroxypropanoate.
Related reactions
12 records
Linked notes
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