2,3-Dihydroxybutanedioic Acid (Tartaric Acid): A Comprehensive Reference
1. Identity, Nomenclature, and Chemical Character
Tartaric acid (2,3-dihydroxybutanedioic acid) is a naturally occurring dicarboxylic acid containing two stereocenters. Also known as acidum tartaricum, it is a white crystalline organic acid found naturally in many fruits, with the molecular formula C₄H₆O₆. The structure of tartaric acid includes two carboxyl groups (–COOH) and two hydroxyl groups (–OH), which make it a chemically active and versatile substance. This alpha-hydroxy-carboxylic acid has a molecular weight of 150.087 g/mol.
The compound is recognized under numerous synonyms in the scientific and regulatory literature. Other documented names include: L-(+)-tartaric acid, natural tartaric acid, threaric acid, dextrotartaric acid, 2,3-dihydroxysuccinic acid, winestone, uvic acid, and racemic acid (the last referring specifically to the racemic mixture). The European food additive code is E334.
1.1 Stereoisomers
Tartaric acid exists as a pair of enantiomers and an achiral meso compound. The dextrorotatory enantiomer of (R,R)-L-(+)-tartaric acid is the form widely distributed in nature. L(+)-Tartaric acid and D(–)-tartaric acid are optically active isomers, rotating the plane of polarized light; these mirror-image molecules (enantiomers) share identical physical and chemical properties except for opposite optical rotations. DL-Tartaric acid (the racemic mixture) is a synthetic equimolar combination of L(+) and D(–) forms, and is optically inactive due to internal compensation. Pure levorotatory (S,S)-D-(−)-tartaric acid is rare in nature.
1.2 Physical Properties
Tartaric acid exists in a white granular to crystalline form. It is an odourless compound with a pleasant acidulous taste. Its melting point is 173.625 °C. This compound is highly soluble in water, primarily due to its ability to form hydrogen bonds with water molecules; the presence of two carboxylic acid groups (–COOH) and hydroxyl groups (–OH) contributes to its high polarity, enhancing its solubility in aqueous solutions.
2. Natural Sources and Botanical Occurrence
Tartaric acid is a naturally occurring organic acid found most abundantly in grapes, where it reaches concentrations of 4 to 8 grams per liter of juice. It is found naturally in many plants, especially in fruits. The highest concentration is seen in grapes, tamarinds, and bananas. It is also present in apricots, oranges, and avocados. Many sour vegetables, including tomatoes, also contain tartaric acid.
Tartaric acid is present in many fruits (as a fruit acid), and its monopotassium salt is found as a deposit during the fermentation of grape juice. Tartaric acid helps to give wine its characteristic 'tartiness,' although the concentration may vary in different grape varieties. The grapes used to make sherry (palomino) have high concentrations of tartaric acid, whereas pinot noir grapes contain little tartrate.
Tartaric acid is a naturally abundant organic acid found mainly in fruits such as grapes, and has known antioxidant and antibacterial properties.
3. Production, Commercial Forms, and Preparations
The exclusive commercial source material comes from natural residues generated during winemaking. These residues primarily contain tartaric acid in the form of potassium bitartrate (cream of tartar) and, to a lesser extent, calcium tartrate.
The L-(+)-tartaric acid isomer is industrially produced in the largest amounts. It is obtained from lees, a solid by-product of fermentations. These by-products mostly consist of potassium bitartrate (KHC₄H₄O₆). Racemic tartaric acid can also be prepared in a multistep reaction from maleic acid.
The compound appears in commerce in several forms:
- Free acid (L-tartaric acid / E334): For food industry purposes, additive E334 is produced from winemaking by-products (such as wine lees and potassium bitartrate), dissolved, purified, and crystallized to yield pure tartaric acid in white powder form.
- Potassium bitartrate (cream of tartar): An important salt of tartaric acid, potassium hydrogen tartarate (cream of tartar), has applications as an acidulant for baking powder and sugar confectionery.
- Rochelle salt (potassium sodium tartrate): This salt has been used as a mild laxative.
- Antimony potassium tartrate (tartar emetic): Some derivatives of tartaric acid, like antimony potassium tartrate, can be found in cough syrups and expectorants.
- Topical cosmetic preparations: In cosmetic products, a recommended dosage of between 5 and 10% is reported, functioning as a pH regulator and masking agent.
4. Historical and Traditional Use
4.1 Ancient and Medieval Use
Historically, the use of tartaric acid dates back to ancient Egyptians, who incorporated it into their food processing techniques. Its role in creating stable wine has been recognized for centuries.
L(+)-tartaric acid derives its name from the medieval, alchemical term tartarus. The process of winemaking — a tradition as old as civilization itself — holds within its folds a series of chemical marvels, one of which is the role of tartaric acid, often referred to as the 'diamonds of wine.'
4.2 Isolation and Early Scientific History
In the 18th century, tartaric acid was first isolated from grapes by Carl Wilhelm Scheele, a Swedish apothecary. Subsequent developments included synthetic production in the late 19th century via maleic anhydride oxidation, and industrial extraction from wine lees, scaling its use in food and textiles.
4.3 Pasteur's Landmark Discovery
Tartaric acid is a historical compound, dating back to when Louis Pasteur separated it into two enantiomers more than 160 years ago. In 1848, Louis Pasteur, a young Agrégé Préparateur at Ecole Normale Supérieure in Paris, was observing crystals of the double sodium–ammonium salt of tartaric acid under a microscope. Pasteur's meticulous examination under a microscope revealed two types of crystals forming from a tartaric acid salt, each being a mirror image of the other. When he separated these crystals and dissolved them in water, he observed that they rotated polarized light in opposite directions. This led to the discovery of enantiomers — molecules that are mirror images of each other but cannot be superimposed.
In 1857, reportedly as a result of a laboratory mishap, Pasteur found that in incubations of ammonium (±)-tartrate with unidentified microorganisms, (+)-tartaric acid was consumed with considerable preference over (–)-tartaric acid. Pasteur's milestone discovery of biological enantioselectivity began the process that in the long run established the fundamental importance of molecular chirality in biology.
4.4 Traditional Persian Medicine
The keyword indexing of the 2024 animal study by Vakili et al. explicitly places tartaric acid research within the context of integrative medicine and traditional Persian medicine, suggesting historical knowledge of the compound's biological properties in that tradition, though detailed historical textual documentation was not located in available peer-reviewed sources and is therefore not elaborated here.
5. Key Constituents and Active Compounds
Tartaric acid itself is the primary bioactive molecule of interest. Its activity is understood primarily through three structural and chemical characteristics:
- Alpha-hydroxy acid (AHA) character: Tartaric acid is an alpha-hydroxy-carboxylic acid. As an AHA, it shares class properties — including keratolytic activity and interaction with skin surface cellular adhesion — with glycolic acid and lactic acid, though tartaric acid is "larger" than glycolic acid and therefore penetrates the skin less deeply.
- Antioxidant properties: Tartaric acid is a naturally abundant organic acid found mainly in fruits such as grapes and has established antioxidant and antibacterial properties.
- Chelating capacity: Tartaric acid in Fehling's solution binds to copper(II) ions, preventing the formation of insoluble hydroxide salts. This chelating action is also recognized in food technology where tartaric acid acts as a metal-ion sequestrant.
6. Established Mechanisms of Action
6.1 AMPK Pathway Activation (Metabolic/Hepatic)
In preclinical research, tartaric acid was found to attenuate oleic acid-stimulated lipid accumulation in HepG2 cells, mainly by activating the AMPK-ACC signaling pathway and suppressing processes such as fatty acid synthesis. The findings demonstrated that tartaric acid could improve body weight gain, fat weight gain, and insulin resistance. The study concluded by identifying tartaric acid as a natural activator of AMPK, which alleviates non-alcoholic fatty liver disease (NAFLD) by attenuating hepatic steatosis, inflammation, and fibrosis.
6.2 eNOS/NO/cGMP Pathway (Cardiovascular)
An important drop in blood pressure was recorded in L-NAME-induced hypertensive rats treated with L-tartaric acid. This molecule also produced a dose-dependent relaxation of the aorta precontracted with norepinephrine and KCl. The study demonstrated that the vasorelaxant capacity of L-tartaric acid appears to be exerted through the activation of eNOS/NO/cGMP pathways.
6.3 Alpha-Hydroxy Acid Keratolytic Action (Dermatological)
Being an alpha-hydroxy acid (AHA), tartaric acid is water-soluble and acts on the skin's surface, primarily targeting signs of aging, spots, acne, and damage caused to the skin by the sun. It breaks down the bonds holding old damaged skin together, causing it to slough off and expose the healthy skin beneath.
6.4 Colonic Transit (Gastrointestinal)
Research found that tartaric acid, either from raisins or as cream of tartar, acted as a good stool softener and shortened intestinal transit time. The mechanism is attributed to the compound's hygroscopic and osmotic properties in the lower gastrointestinal tract, though specific mechanistic studies in humans are limited.
7. Scientific Evidence by Area of Application
7.1 Gastrointestinal and Colonic Health
Human/Clinical Evidence (moderate quality, small scale):
Spiller et al. (published in the British Journal of Nutrition, 2003) studied the effects of tartaric acid on colonic function, noting that the effects on colon function had not been the focus of extensive research. The study evaluated effects of dietary fibre and tartaric acid from sun-dried raisins on colon function and on faecal bile acid and short-chain fatty acid (SCFA) excretion in healthy adults.
Thirteen healthy subjects (seven males and six females; 27–65 years of age) were fed 5 g cream of tartar (monopotassium tartrate) or 120 g sun-dried raisins — both equal to approximately 2 g tartaric acid — per day for 9 weeks, divided into 3-week cycles.
Key outcomes reported:
- Both sun-dried raisins and cream of tartar appeared to be good stool softeners and to shorten intestinal transit time, although the fibre in sun-dried raisins had the added benefit of increasing faecal weight.
- For nine weeks, intestinal transit time was 42 hours on the baseline diet, 31 hours on the cream of tartar arm.
- Sun-dried raisins caused significant reductions in total bile acid concentration (from 1.42 to 1.09 mg/g, P<0.05), whereas cream of tartar did not achieve a statistically significant reduction. Sun-dried raisins also significantly reduced the lithocholic-to-deoxylithocholic acid (LC:DC) ratio (P<0.02), whereas cream of tartar reduced the ratio only to a lesser, non-significant extent.
- Sun-dried raisins increased total SCFA excretion (from 5.6 to 7.6 g/4 d, P<0.05), which remained unchanged with cream of tartar.
Evidence assessment: This is a single small crossover study (n=13) in healthy adults. It provides direct human evidence that a dose of approximately 2 g/day of tartaric acid as cream of tartar shortens intestinal transit time and softens stool. The bile acid–modulating and SCFA effects seen with raisins appear primarily attributable to the dietary fibre component rather than to tartaric acid alone. The evidence base is preliminary and has not been replicated in larger, controlled trials.
7.2 Hepatic and Metabolic Health (NAFLD / Obesity / Insulin Resistance)
Preclinical Evidence Only:
In a study published in the European Journal of Pharmacology (2024), tartaric acid was found to alleviate obesity, insulin resistance, hepatic steatosis, inflammation, and fibrosis in a Western diet-induced mouse model of NAFLD. Furthermore, tartaric acid attenuated oleic acid-stimulated lipid accumulation in HepG2 cells, mainly by activating the AMPK-ACC signaling pathway and suppressing processes such as fatty acid synthesis. The authors concluded that tartaric acid may be a potential therapeutic agent for improving the disease progression of NAFLD.
Evidence assessment: This evidence is restricted to animal (mouse) and cell culture (HepG2) models. No human clinical trials on tartaric acid for NAFLD have been identified in the available literature. The findings are mechanistically plausible given the centrality of the AMPK pathway in lipid metabolism but should be regarded as preliminary hypothesis-generating data only.
7.3 Cardiovascular Health (Hypertension and Vasorelaxation)
Preclinical Evidence Only:
A study published in Cardiovascular & Hematological Agents in Medicinal Chemistry (2023) aimed to assess the effect of acute and subchronic administration of L-tartaric acid on blood pressure parameters in normotensive and hypertensive rats as well as its vasorelaxant potency. L-NAME-induced hypertensive and normotensive rats received L-tartaric acid (80 and 240 mg/kg) orally over six hours for the acute experiment and seven days for the subchronic treatment; thereafter systolic, diastolic, mean arterial blood pressure, pulse pressure, and heart rate were evaluated. An important drop in blood pressure was recorded in L-NAME-induced hypertensives treated with L-tartaric acid. The molecule also produced a dose-dependent relaxation of the aorta precontracted with norepinephrine and KCl.
Tartaric acid was described as capable of balancing blood pressure and noted as the main constituent of classically recognized antihypertensive agents (grapes and wine), while also being identified as not yet having been fully scientifically explored as an antihypertensive remedy.
Evidence assessment: All cardiovascular evidence is from rodent in vivo and ex vivo aortic ring preparations. No human interventional data are available. The studies identify biologically plausible mechanisms but findings in animal hypertension models do not translate directly to human cardiovascular benefit.
7.4 Reproductive Health / Polycystic Ovary Syndrome (PCOS)
Preclinical Evidence Only:
Polycystic ovary syndrome (PCOS) is the most common endocrine-related reproductive disorder in women of reproductive age, accompanied by impairment of female fecundity and a risk of metabolic disorders. A 2024 study aimed to evaluate the effects of L-tartaric acid, an abundantly occurring compound in fruits, on the histostereological and hormonal changes caused by PCOS.
Forty adult Sprague-Dawley rats were randomly divided into four groups including controls (no intervention), tartaric acid (40 mg/kg/day from day 21 onwards for 39 days), PCOS (induced by letrozole), and PCOS + tartaric acid. After treatments, ovarian histostereological analysis as well as reproductive hormones — including LH, FSH, estradiol, progesterone, and testosterone — were measured.
The administration of tartaric acid restored the pathological effects of PCOS on the ovarian histostructure. Furthermore, tartaric acid improved the serum levels of LH, estradiol, progesterone, and testosterone (p-value < 0.05). The obtained findings may suggest tartaric acid as a novel strategy for PCOS management, although further studies are necessary.
Evidence assessment: Entirely preclinical (animal model only). No human data exist. The study used a letrozole-induced PCOS rat model, which, while widely used, has acknowledged limitations in translating to human PCOS. These findings are exploratory.
7.5 Inflammatory Bowel Disease / Colitis
Preclinical evidence — with an important cautionary finding:
A 2025 study published in Pathogens (MDPI) investigated the effects of tartaric acid on eosinophil activation in a dextran sulfate sodium (DSS)-induced colitis model. Dietary factors, including certain organic acids, can influence ulcerative colitis progression by modulating gut immune responses. This research was the first to explore the dose-dependent effects of tartaric acid (TA), a naturally occurring organic acid widely used in the food industry, on eosinophil activation and Th2 cytokine response in both normal mice and a DSS-induced colitis model.
Normal mice were treated with TA at varying doses (5 µg, 25 µg, and 50 µg/mouse/day), while colitis mice received 50 µg TA. Eosinophil activation markers (CD11b+, SiglecF+, and CCR3+), Th2 cytokines (IL-4, IL-13, and IL-31), and IL-17 were assessed in peripheral blood leukocytes, lymph nodes, and splenocytes using flow cytometry. Results demonstrated a dose-dependent effect of TA, with the highest dose significantly increasing eosinophil activation markers, Th2 cytokines, IL-17, and mRNA expression of SiglecF, CCL11, and toll-like receptor-related genes.
Evidence assessment: This preclinical finding suggests that at high doses, tartaric acid may exacerbate eosinophilic inflammation in experimental colitis — a safety-relevant cautionary signal that runs counter to a simple pro-health narrative. This finding requires further study and has not been examined in humans.
7.6 Dermatological / Topical Applications
Mechanistic and class-level evidence; limited direct clinical trial data for tartaric acid specifically:
Tartaric acid has antioxidant properties and is classified as an alpha-hydroxy acid (AHA). AHAs are widely used acids in skincare products such as serums and masks. Due to its antioxidant and exfoliation properties, it is most often used for reducing fine lines and wrinkles, hyperpigmentation, acne, large pores, and dull or uneven skin tone. It acts as a natural exfoliator because it encourages the shedding of the outer layer of skin cells.
Beyond its industrial uses, tartaric acid has become a common ingredient in skincare products due to its keratolytic and astringent properties. Generally, tartaric acid is used in topical preparations at concentrations ranging from 1 to 10%.
Evidence assessment: The topical use of AHAs is supported by a substantial body of dermatological evidence at the class level. However, high-quality, randomized controlled trials examining tartaric acid specifically as a stand-alone topical therapeutic ingredient are sparse in the peer-reviewed literature. Most available evidence concerns AHAs as a class or formulations combining multiple AHAs. Tartaric acid's larger molecular size relative to glycolic acid is documented, but the clinical significance of differential skin penetration depth has not been well-characterized in trials specific to this compound.
7.7 Respiratory / Cough Research
Tartaric acid has been employed experimentally as a cough stimulus in clinical research. Fujimura et al. (1992) investigated the cough threshold to inhaled tartaric acid and bronchial responsiveness to methacholine in patients with asthma and sino-bronchial syndrome, published in Internal Medicine. In this context tartaric acid serves as a pharmacological research probe rather than a therapeutic agent. People use tartaric acid for asthma and swallowing problems, but there is no good scientific evidence to support these uses.
8. Body Systems and Health Areas of Association
- Gastrointestinal tract: Laxative effect (stool softening, transit-time reduction), bile acid modulation. Supported by one small human crossover study.
- Liver and metabolic function: AMPK activation, anti-steatotic, anti-inflammatory, and anti-fibrotic effects in animal/cell models of NAFLD.
- Cardiovascular system: Antihypertensive and vasorelaxant activity via the eNOS/NO/cGMP pathway in rodent models.
- Endocrine/reproductive system: Ovarian histostructure and hormone normalization in an animal model of PCOS.
- Integument (skin): Exfoliation, keratolysis, pH regulation, and antioxidant activity in topical formulations.
- Immune system (colonic, with caution): May upregulate eosinophilic inflammation at high doses in colitis animal models.
9. Dosage Forms and Reported Dosages
The following dosages have been reported in the scientific literature reviewed; they are reproduced descriptively and not as recommendations:
- Human gastrointestinal study: 5 g cream of tartar (monopotassium tartrate) per day — equivalent to approximately 2 g tartaric acid — administered daily for 9 weeks in 13 healthy adults (crossover design).
- Rat antihypertensive study: L-tartaric acid was administered at doses of 80 and 240 mg/kg orally to L-NAME-induced hypertensive and normotensive rats over six hours for the acute experiment and seven days for the subchronic treatment.
- Rat PCOS study: Tartaric acid was administered at 40 mg/kg/day from day 21 onwards for 39 days to Sprague-Dawley rats.
- Mouse colitis study: Mice were treated with TA at varying doses of 5 µg, 25 µg, and 50 µg/mouse/day; colitis mice received 50 µg TA.
- Cosmetic/topical use: Tartaric acid is used in topical preparations at concentrations generally ranging from 1 to 10%.
- As a medicine: There is not enough reliable information to know what an appropriate dose of tartaric acid might be for therapeutic purposes.
10. Safety, Toxicology, and Regulatory Status
10.1 Regulatory Classifications
Tartaric acid has been approved as a safe ingredient by the U.S. Food and Drug Administration (FDA), the European Food Safety Authority (EFSA), and the Joint FAO/WHO Expert Committee on Food Additives (JECFA). L-(+)-tartaric acid obtained from winemaking is generally recognized as safe (GRAS) as a direct human food ingredient and can be used as a firming agent, flavor enhancer, flavoring agent, pH control agent, and humectant in food with no limitation other than current good manufacturing practice.
L-tartaric acid (E334) is listed in Commission Regulation (EU) No 231/2012 as an authorised food additive and categorised in "Additives other than colours and sweeteners."
10.2 Acceptable Daily Intake (ADI)
A group ADI of 240 mg/kg body weight per day, expressed as tartaric acid, for L(+)-tartaric acid–tartrates (E334–337, 354) has been established by the EFSA FAF Panel in 2020.
10.3 Preclinical Toxicological Data
The EFSA Panel on Food Additives and Flavourings (FAF) assessed the impact of tartaric acid on human health. It reported that doses up to 3,100 mg/kg body weight per day in rat studies caused no toxic effects, including no nephrotoxicity and no carcinogenicity. It also noted that humans absorb less tartaric acid than rats. Genotoxicity and reproductive toxicity were not observed in the studies.
10.4 Stereoisomer-Specific Safety
The EFSA Panel noted that only L(+)-tartaric acid is authorised for use as food additive E334. Given the adverse effects reported for DL-tartaric acid (EFSA FAF Panel, 2020), only L(+)-tartaric acid should be used for the manufacturing process of food additives containing tartaric acid. Based on toxicological data and regulatory standards, L(+)-tartaric acid is preferred in winemaking due to its natural origin and metabolic compatibility.
10.5 High-Dose and Concentrated Exposure Risks
When consumed in overwhelming amounts, the acid can act as a direct corrosive irritant to the gastrointestinal lining. Systemically, large doses of tartaric acid can disrupt the body's electrolyte balance and impair kidney function. The kidneys may struggle to process and excrete the acid load, which can lead to severe metabolic acidosis. These risks are associated with concentrated or massive ingestion well beyond dietary exposure levels and are not representative of typical food or supplement use.
10.6 Topical Use Considerations
Excessive use of alpha-hydroxy acid treatments including tartaric acid can cause local irritations, pain, a sensation of itching, oedema, and redness in the treated area. It is advisable to use it during the evening daily routine to minimize any risk of photosensitivity. Tartaric acid increases the skin's sensitivity to the sun, and thus the risk of sunburn.
10.7 Inflammatory Bowel Disease Signal
As noted in Section 7.5, the 2025 preclinical study indicated that the highest dose tested significantly increased eosinophil activation markers, Th2 cytokines, IL-17, and mRNA expression of SiglecF, CCL11, and toll-like receptor-related genes in a mouse model of colitis. While this was an animal study using doses not directly translatable to human supplemental doses, it represents a biologically relevant caution for individuals with or at risk for eosinophil-mediated gastrointestinal conditions.
10.8 Known Drug Interactions
Specific well-characterized pharmacokinetic or pharmacodynamic drug–drug interactions for tartaric acid consumed as a dietary supplement are not documented in the peer-reviewed sources accessed. Tartaric acid functions as an excipient in many pharmaceutical preparations (e.g., effervescent tablets, oral solutions) where it acts as an acidulant; in this context it may affect the rate of dissolution and absorption of co-formulated drugs through pH modification, but this is a formulation-level consideration rather than a systemic interaction.
11. Overall Evidence Summary
Tartaric acid (2,3-dihydroxybutanedioic acid) has a well-established role as a food acidulant, winemaking stabilizer, and AHA-class cosmetic ingredient, each supported by regulatory approvals and mechanistic evidence. However, people's uses of tartaric acid as a medicine for conditions such as asthma and swallowing problems are not supported by good scientific evidence. The most credible human-level clinical evidence supports its acute laxative/transit-shortening effect at approximately 2 g/day, derived from a single small crossover study. All evidence for hepatic, cardiovascular, and reproductive applications remains at the preclinical (animal or cell culture) stage. The available preclinical data — including the AMPK activation pathway for NAFLD, eNOS/NO/cGMP-mediated antihypertensive effects, and ovarian hormone normalization in PCOS — represents mechanistically coherent but not yet clinically validated findings. A cautionary preclinical signal regarding exacerbation of eosinophilic colonic inflammation at high doses warrants continued investigation. Regulatory bodies in the US (FDA), EU (EFSA), and internationally (JECFA) have established the safety of L(+)-tartaric acid as a food additive within approved use levels.
References
- ScienceDirect Topics — Tartaric Acid: An Overview
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