L-Tartaric acid

HCID 178538632CAS 144814-09-5

Basic information

Standard SMILES
O=C(O)[C@H](O)[C@@H](O)C(=O)O
InChIKey
FEWJPZIEWOKRBE-JCYAYHJZSA-N
Molecular formula
C4H6O6
Average molar mass
150.09 g/mol

Overview

L-tartaric acid is the L-enantiomer of tartaric acid. It is a conjugate acid of a L-tartrate(1-). It is an enantiomer of a D-tartaric acid.

Names & identifiers

Preferred name
L-Tartaric acid
IUPAC
(2R,3R)-2,3-dihydroxybutanedioic acid
English name
lamB protein (fungal)
Molecular formula
C4H6O6
Molecular weight
150.08684

Names & synonyms

L-tartaric acid87-69-4L-(+)-Tartaric acidL(+)-Tartaric acidtartaric acid(2R,3R)-2,3-dihydroxysuccinic acid(2R,3R)-2,3-dihydroxybutanedioic acid(+)-Tartaric acid(+)-L-Tartaric acid(R,R)-Tartaric acidThrearic acidDextrotartaric acid
Show more names
lamB protein (fungal)
L-threaric acidNatural tartaric acid(+)-(R,R)-Tartaric acid(2R,3R)-Tartaric acidRechtsweinsaeureKyselina vinna(R,R)-(+)-Tartaric acidFEMA No. 3044

Database identifiers

CAS
144814-09-5
ChEMBL
CHEMBL1236315
ChEBI
CHEBI:15671
UNII
4J4Z8788N8、W4888I119H
EC Number
201-766-0、205-105-7
Nikkaji
J31.839F

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

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Organic Acids

Other Classes -> Organic Acids

CosmeticsBuffering
Fragrances · 2 items

Fragrance Ingredient ((+)-Tartaric acid) -> IFRA transparency List

Fragrance Ingredient (Tartaric acid (d-, l-, dl-, meso-)) -> IFRA transparency List

LogP · 2 items

-0.76 (calculated)

-1.2

Food AdditivesANTICAKING AGENT OR FREE-FLOW AGENT, DRYING AGENT, FIRMING AGENT, FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, HUMECTANT, LEAVENING AGENT, PH CONTROL AGENT -> FDA Substance added to food
Density · 2 items

Relative density (water = 1): 1.79

1.76 @25 °C

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.9% (44 of 4731) of reports.

Danger

H302 (42.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4731 reports by companies from 33 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 5.1% (26 of 506) of reports.

Hazard information

Regulatory Information · 6 items

Chemical: Butanedioic acid, 2,3-dihydroxy- (2R,3R)-

Chemical: Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(.+-.)-

Regulation (EC) No 1333/2008 (amended)

Butanedioic acid, 2,3-dihydroxy- (2R,3R)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanedioic acid, 2,3-dihydroxy- (2R,3R)- 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: 04-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15126

Status: Active Update: 03-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34095

Other Safety Information · 2 items

IMAP assessments - Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(.+-.)-: Human health tier I assessment

IMAP assessments - Butanedioic acid, 2,3-dihydroxy- [R-(R*,R*)]-: Human health tier I assessment

Fire HazardsCombustible.
Hazards Summary · 2 items

Causes burns; Inhalation of aerosol may cause pulmonary edema; [ICSC] An irritant; [Acros Organics MSDS]

A local irritant; [Merck Index] May cause serious eye injury; [ECHA REACH Registrations] Maximum total daily intake of tartrate of 0-6 mg/kg (unconditional acceptance) and 6-20 mg/kg (conditional acceptance); [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS]

EPA Safer ChemicalChemical: Tartaric acid
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.

Safety & protection

Fire FightingUse water spray, powder, foam, carbon dioxide.
First Aid Measures · 4 items

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.
Exposure Control and Personal Protection2.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Spillage Disposal · 1 item

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.

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms · 4 items

Cough. Sore throat. Burning sensation.

Redness.

Redness. Pain. Severe burns.

Cough. Sore throat. Burning sensation. Nausea. Vomiting.

Human Toxicity ExcerptsA fatal tubular nephropathy occurred in an adult male who accidentally ingested about 30 grams of tartaric acid.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 1 item

The authors of this 2022 publication looked at ASPCA Animal Poison Control Center electronic database reports of dogs that developed acute kidney injury following ingestion of cream of tartar (potassium bitartrate) or tamarinds. They noted that the clinical signs, laboratory findings, and histopathologic lesions were similar to those reported in the grape and raisin toxicosis found in dogs. Given the sensitivity of dogs to tartaric acid, the authors proposed that tartaric acid is the likely toxic component associated with both grape and tamarind acute kidney injury. These authors also noted that detartration (removal of tartrates) of processed products could explain the lack of reported toxicosis following exposure to agents such as grape juice, jam, and wine. Further, the authors noted that thermal decomposition of tartaric acid may explain the anecdotal observation that cooked grapes and raisins

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

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.

Metabolism/MetabolitesMost tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract , primarily in the large instestine.
Absorption, Distribution and Excretion · 2 items

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.

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

Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 4 items

Used as a synergist for antioxidants, acid, emulsifier, sequestrant, and flavoring agent; [JECFA]

Levo form of dextrorotatory tartaric acid; Found throughout nature and classified as a fruit acid; Used in soft drinks and foods, as an acidulant, complexing agent, pharmaceutic aid (buffering agent), in photography, tanning, ceramics, and to make tartrates; Diethyl and dibutyl ester derivatives are commercially significant for use in lacquers and in textile printing; [Merck Index] Used as an intermediate, in construction and ceramics applications, in cleaning products, cosmetics/personal care products, and metal surface treatments (including galvanic and electroplating products); [ECHA REACH Registrations] Used as a flavoring agent, anticaking agent, drying agent, firming agent, humectant, leavening agent, and pH control agent for foods; [FDA] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Electroplating [Category: Plate]

Use (kg; approx.) in Germany (2009): >1000

U.S. Production2023: 100,000 - <250,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry Uses · 2 items

Other

The authors report that the electrowinning of ternary lithium-ion battery leachates using tartaric acid achieves 99.1% cobalt purity in a batch mode, and high puriity and high recovery of metallic cobalt, nickel , and manganese dioxide in a scalable flow system.

Household ProductsInformation on 7 consumer products that contain Tartaric acid in the following categories is provided:
Use Classification · 6 items

EPA Safer Chemical Functional Use Classes -> Processing Aids and Additives

Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern

Food additives

Fragrance Ingredients

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENTFood Additives -> ACID; ANTIOXIDANT_SYNERGIST; EMULSIFIER; SEQUESTRANT; SYNERGIST -> JECFA Functional Classes

Additional notes

DefinitionChEBI: L-tartaric acid is a tartaric acid. It is a conjugate acid of a L-tartrate(1-). It is an enantiomer of a D-tartaric acid.

Related reactions

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