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Caproic acid
Caproic acid
Caproic acid
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Caproic acid
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Hexanoic acid
Other names
Hexoic acid; Hexylic acid; Butylacetic acid; Pentylformic acid; 1-Pentanecarboxylic acid; C6:0 (Lipid numbers)
Identifiers
3D model (JSmol)
773837
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.046 Edit this at Wikidata
EC Number
  • 205-550-7
185066
KEGG
UNII
  • InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) checkY
    Key: FUZZWVXGSFPDMH-UHFFFAOYSA-N checkY
  • InChI=1/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
    Key: FUZZWVXGSFPDMH-UHFFFAOYAY
  • CCCCCC(=O)O
Properties
C6H12O2
Molar mass 116.160 g·mol−1
Appearance Oily liquid[1]
Odor goat-like
Density 0.929 g/cm3[2]
Melting point −3.4 °C (25.9 °F; 269.8 K)[1]
Boiling point 205.8 °C (402.4 °F; 478.9 K)[1]
1.082 g/100 mL[1]
Solubility soluble in ethanol, ether
Acidity (pKa) 4.88
−78.55·10−6 cm3/mol
1.4170
Viscosity 3.1 mP
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P260, P264, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P361, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 103 °C (217 °F; 376 K)[2]
380 °C (716 °F; 653 K)
Explosive limits 1.3-9.3%
Lethal dose or concentration (LD, LC):
3000 mg/kg (rat, oral)
Related compounds
Related compounds
 Pentanoic acid, Heptanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Caproic acid, also known as hexanoic acid, is the carboxylic acid derived from hexane with the chemical formula CH3(CH2)4COOH. It is a colorless oily liquid with a fatty, cheesy, waxy odor resembling that of goats[1] or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor.[3] It is also one of the components of vanilla and cheese. The primary use of caproic acid is in the manufacture of its esters for use as artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols.[1] Salts and esters of caproic acid are known as caproates or hexanoates. Several progestin medications are caproate esters, such as hydroxyprogesterone caproate and gestonorone caproate.

Two other acids are named after goats: caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15% of the fat in goat's milk.

Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other two are mobile liquids) are not only used for the formation of esters, but also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.

See also

[edit]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Caproic acid

View on Grokipedia
from Grokipedia
Caproic acid, also known as hexanoic acid, is a straight-chain saturated with the molecular formula C₆H₁₂O₂ and a molecular weight of 116.16 g/mol. It appears as a colorless to light yellow liquid or white crystalline solid with a pungent, unpleasant reminiscent of rancid , and it has a of approximately -3.4 °C and a of 205 °C. Slightly soluble in (about 10.6 g/L at 20 °C), it is miscible with ethanol and , and its ranges from 0.923 to 0.929 g/cm³. Naturally occurring in various animal fats and vegetable oils, caproic acid constitutes around 2% of bovine milk fat and is present in smaller amounts in , , and fruits like . As a medium-chain , it plays a role in and is a . In biological systems, it serves as a conjugate acid of hexanoate and is involved in pathways. Industrially, caproic acid is valued for its versatility as a precursor in synthesizing esters for flavors and fragrances, lubricants, additives, and pharmaceuticals, and it is also used as a agent in products, baked goods, and to impart creamy or fruity notes. It finds applications in rubber chemicals, , and as an additive in or antibacterial formulations, with production often derived from organic waste or of natural fats. Safety-wise, caproic acid is corrosive, causing severe burns, eye , and respiratory upon exposure, and it is classified under GHS as or inhaled, necessitating protective handling in occupational settings.

Properties

Physical properties

Caproic acid, also known as hexanoic acid, has the C₆H₁₂O₂, often written as CH₃(CH₂)₄COOH, and a molecular weight of 116.16 g/mol. It appears as a colorless oily at but forms a white crystalline solid at low temperatures. The compound emits a pungent, goat-like or rancid odor, which contributes to its characteristic smell in natural sources such as certain cheeses. Caproic acid melts at -3.4 °C and boils at 205.8 °C under standard atmospheric pressure. Its is 0.927–0.929 g/cm³ at 20 °C. The acid exhibits limited in at 1.03 g/100 mL (25 °C) but is miscible with and . Its measures 0.0435 mmHg at 25 °C, with a of 102–103 °C. The octanol-water partition coefficient (log P) is 1.92, reflecting its moderate hydrophobicity.

Chemical properties

Caproic acid, also known as hexanoic acid, exhibits typical reactivity as a straight-chain carboxylic acid, characterized by its ability to donate a proton in aqueous solutions, resulting in the formation of the conjugate base hexanoate ion. The acid dissociation constant (pKa) for caproic acid is 4.88 at 25 °C, indicating moderate acidity typical of aliphatic carboxylic acids, where it exists predominantly in its anionic form under neutral to basic environmental conditions. This proton donation enables caproic acid to react with bases, forming water-soluble salts; for example, neutralization with yields sodium caproate (CH₃(CH₂)₄COONa), a that evolves and is representative of carboxylic acid-base interactions. In esterification reactions, caproic acid condenses with alcohols in the presence of an acid catalyst to produce esters and , as shown in the general equilibrium: RCOOH+R’OH⇌RCOOR’+H2O\text{RCOOH} + \text{R'OH} \rightleftharpoons \text{RCOOR'} + \text{H}_2\text{O} A common example is the formation of ethyl hexanoate from caproic acid and ethanol, which is utilized in flavor synthesis. Caproic acid demonstrates stability under normal ambient conditions but can undergo oxidation when exposed to strong oxidizing agents, potentially yielding dicarboxylic acids such as adipic acid through ω-oxidation pathways under vigorous conditions.

Occurrence

In nature

Caproic acid is found in various animal fats and oils, notably comprising 2–3% of the total fatty acids in , from which it derives its name (from the Latin , meaning ). In plant sources, caproic acid occurs at low levels, such as less than 1% in (approximately 0.5%) and (approximately 0.3%). It is also present in the seed coats of , where it contributes to the foul odor released during decomposition, alongside other like . Additionally, caproic acid appears in cured beans in trace amounts, typically ranging from 0.05 to 0.38 mg/kg depending on the variety. Dairy products derived from these fats, such as , contain caproic acid, with levels up to 1–2% of total fatty acids in varieties like , where it imparts characteristic flavors. Caproic acid exists in trace amounts in certain fruits and wines; for example, concentrations range from less than 10 to 982 µg/kg in fruit, and 1.2–12.3 mg/L in fruit wines like wine. In the environment, caproic acid has been detected at low levels, such as 0.063 in automotive exhaust from vehicles, and it occurs naturally in some essential oils, including those from lavender and palmarosa. Its accumulation in decaying matter often results from brief microbial action on organic substrates.

In biological systems

Caproic acid, a short-chain (SCFA), is produced in the human gut by anaerobic bacteria through the of dietary fibers, although it constitutes a minor fraction compared to , propionate, and butyrate. Specific members, such as species, directly generate caproic acid during this process, contributing to the overall SCFA pool that supports intestinal . In ruminant animals, caproic acid is generated in the via chain elongation by bacteria including Clostridium kluyveri, which elongates shorter chain fatty acids derived from plant material fermentation. This process occurs through reverse β-oxidation, where or butyrate serves as the carbon backbone, elongated using electron donors like or lactate. Physiologically, caproic acid serves as an energy source for colonocytes, similar to other SCFAs, by providing for cellular metabolism in the . It also influences the composition and helps maintain an acidic pH in the colon, which inhibits and promotes microbial diversity. In mammalian fats, caproic acid is present at approximately 2% of total fatty acids, varying slightly by species such as 2.4% in bovine . Once absorbed, caproic acid is metabolized in mitochondria via β-oxidation to , entering the for energy production.

Production

Biosynthesis

Caproic acid is primarily biosynthesized through the reverse β-oxidation pathway in anaerobic bacteria, such as Clostridium kluyveri, where like and serve as substrates for chain elongation. This pathway involves key enzymes including for the condensation of with to form β-ketoacyl-CoA, 3-hydroxyacyl-CoA dehydrogenase for reduction to β-hydroxyacyl-CoA, enoyl-CoA hydratase for dehydration, and enoyl-CoA reductase for the final reduction to elongated , with facilitating the initial oxidation of to . The process iteratively adds two-carbon units, starting typically from or butyryl-CoA derived from or metabolism. In the chain elongation mechanism, acts as an while provides the carbon backbone, leading to the net reaction: 2CH3CH2OH+2CH3COOH→CH3(CH2)4COOH+2CO2+4H22 \text{CH}_3\text{CH}_2\text{OH} + 2 \text{CH}_3\text{COOH} \rightarrow \text{CH}_3(\text{CH}_2)_4\text{COOH} + 2 \text{CO}_2 + 4 \text{H}_2 This thermodynamically favorable process under anaerobic conditions extends the chain to produce caproic acid (C6) from shorter precursors. The pathway is coupled with ATP generation via proton-translocating enzymes, enhancing energy efficiency in these microbes. Biosynthesis occurs via anaerobic fermentation of organic wastes, such as food scraps or , using mixed microbial cultures enriched for chain-elongating in bioreactors. Optimal conditions include a of 5–6 and temperatures of 30–37 °C, which favor the activity of species and maintain process stability. Laboratory-scale yields demonstrate conversion efficiency from lignocellulosic or carbohydrate-rich feedstocks, with reported values up to 0.3 g/g in optimized systems. Emerging biotechnological approaches involve to enhance production, such as modifying by introducing reverse β-oxidation modules to achieve titers over 1 g/L of medium-chain fatty acids like caproic acid under aerobic conditions. Similarly, of yeasts and strains optimizes enzyme expression and reduces byproducts, improving scalability for industrial applications.

Industrial production

Caproic acid is produced industrially as a during the of and oils, where it comprises approximately 0.5 wt% of the resulting mixture from splitting processes conducted at high temperatures (240–260°C) and pressures (45–50 bar). This method leverages the natural occurrence of caproic acid in these oils, followed by for purification to achieve grades such as 98% minimum purity. The global caproic acid market reached approximately USD 520 million in 2025, driven by demand in flavors, pharmaceuticals, and bio-based chemicals, with an expected (CAGR) of 6–8% through 2035 due to the shift toward sustainable production routes. routes involve the oxidation of n-hexanol to caproic acid using air or as oxidants, represented by the reaction CH3(CH2)4CH2OH+O2→CH3(CH2)4COOH+H2O\mathrm{CH_3(CH_2)_4CH_2OH + O_2 \rightarrow CH_3(CH_2)_4COOH + H_2O} This process converts the to the corresponding under controlled conditions to minimize over-oxidation. Hydrogenation methods include the catalytic reduction of (2,4-hexadienoic acid) to caproic acid using catalysts like (Pd/C) under pressure, achieving full saturation of the double bonds to yield hexanoic acid as the product. Similar reductions can employ as a precursor, though less commonly scaled due to the need for steps. Catalytic processes encompass the reduction of the corresponding β-lactone intermediate using heterogeneous catalysts, as patented for efficient conversion to caproic acid, and of to hexanal followed by oxidation to yield the C6 carboxylic acid. Fermentation-based industrial production relies on anaerobic elongation in , utilizing feedstocks such as , , or agricultural wastes to extend short-chain acids like or butyrate into caproic acid via reverse β-oxidation pathways. Pilot-scale operations have demonstrated titers of 10–50 g/L, with examples reaching 23.4 g/L from lactate substrates using isolated strains like Ruminococcaceae bacterium CPB6, and broader mixed-culture systems processing food waste or thin stillage at rates suitable for . As of 2025, advancements in design have improved yields to up to 50 g/L in continuous systems. These semi-biological approaches adapt biosynthetic mechanisms for enhanced scalability and .

Uses

Flavor and fragrance applications

Caproic acid, also known as hexanoic acid, plays a key role in the flavor and fragrance industries due to its pungent, rancid odor reminiscent of cheese, sweat, and fatty notes, which is harnessed in synthetic formulations. It is primarily utilized in the production of esters, such as methyl hexanoate and ethyl hexanoate, which impart fruity profiles like pineapple, apple, and apricot to various products. These esters are incorporated into beverages, candies, and baked goods to enhance sweet, tropical, or creamy flavors, with ethyl hexanoate specifically contributing to apple-like aromas in food applications. In fragrance applications, caproic acid contributes goaty and fatty undertones to perfumes and , often blended to create complex, animalic scents in lavender-based compositions or as a base note in . A significant portion of caproic acid production is directed toward flavor and fragrance esters, underscoring its importance in these sectors. The U.S. recognizes caproic acid as (GRAS) for use as a synthetic substance and adjuvant in food, permitting addition at low levels typically up to 0.05% in finished products to avoid . Specific examples include its role in enhancing rancid or sweaty notes for artificial cheese flavors, where it mimics the sharp tang of aged dairy. Caproic acid is also detected in natural vanilla extracts, contributing subtle fatty and sour undertones that support the overall aromatic profile. Its natural occurrence in dairy products further informs these synthetic applications, providing a basis for authentic flavor replication.

Pharmaceutical applications

Caproic acid plays a key role in pharmaceutical applications primarily through its derivatives as ester prodrugs, where the caproate group enhances by increasing and enabling sustained release of the active moiety. This modification allows for improved and reduced dosing frequency compared to the parent compounds. A key example is , a synthetic progestin that was approved by the FDA in for administration via to prevent in women with a singleton pregnancy and a history of preterm delivery. However, the FDA withdrew approval in April 2023 after confirmatory trials failed to demonstrate a clinical benefit. The caproate chain in this derivative prolongs the of the progesterone analog, facilitating slow release and maintaining therapeutic levels over time. Its is C27H40O4C_{27}H_{40}O_4. Gestonorone caproate represents another important caproate , functioning as a potent progestin for treating and related gynecological conditions by stabilizing the and exerting anti-estrogenic effects. Beyond human , caproic acid finds use in veterinary applications, where it is added to animal feeds to promote growth in such as piglets and calves, primarily through its activity that supports gut health and nutrient utilization. It also contributes to pharmaceutical formulations, inhibiting bacterial proliferation in targeted therapies. Pharmaceutical demand drives a notable portion of caproic acid usage, with reproductive drugs like gestonorone caproate being contributors.

Other industrial applications

Caproic acid serves as a component in the formulation of lubricants and greases, where it functions as an additive to modify in metalworking fluids, enhancing their performance in industrial operations. Its incorporation helps improve and stability under high-temperature and high-pressure conditions typical of environments. In the rubber and plastics sector, caproic acid is utilized in the synthesis of plasticizers for synthetic rubbers, including rubber, to enhance flexibility, durability, and processing characteristics of the materials. such as hexyl esters of caproic acid may also contribute to formulations in production, aiding in compatibility and performance optimization. As a chemical intermediate, caproic acid supports the production of various esters and derivatives used in industrial syntheses, though it is not a direct precursor in standard routes to for nylon-6 manufacturing. Caproic acid functions as an agent in preservatives for and textiles, leveraging its antibacterial properties effective at low concentrations to inhibit microbial growth and extend product . In , it is particularly valued for its ability to disrupt bacterial cell membranes without compromising formulation integrity. Emerging applications of caproic acid include its role in biofuels and bioplastics, produced as a high-value medium-chain through microbial chain elongation processes that convert organic waste streams into renewable chemicals. This approach utilizes reverse β-oxidation pathways in anaerobic microbiomes to elongate short-chain acids like into caproic acid, which can serve as a feedstock for esters or monomers.

Safety and toxicology

Health hazards

Caproic acid, also known as hexanoic acid, presents health hazards mainly due to its corrosive nature and irritant effects on human tissues, with low overall systemic toxicity. It is classified under the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) as causing skin corrosion (Category 1C) and serious eye damage (Category 1), leading to severe burns upon direct contact. Acute toxicity is relatively low, with an oral LD50 of 3,000 mg/kg in rats, indicating minimal risk of systemic poisoning from ingestion alone, though local effects remain significant. Dermal exposure results in severe burns and rapid absorption, exacerbating irritation. Inhalation irritates the , with an LC50 of 2.05 mg/L (4 hours) in mice, and can cause coughing, , or at high concentrations. Ingestion leads to gastrointestinal irritation, including , , and potential burns to the digestive tract. Chronic exposure may result in persistent irritation or from repeated contact, though it is not considered a strong skin sensitizer based on available data. The National Institute for Occupational Safety and Health (NIOSH) estimated approximately 10,000 U.S. workers exposed annually between and 1983, a figure still referenced for occupational . Immediate for exposure involves flushing affected skin or eyes with copious amounts of water for at least to minimize damage; medical attention is essential for or cases to monitor for delayed effects like . Handling requires , including chemical-resistant gloves, safety goggles, and protective clothing, to prevent contact. No specific OSHA (PEL) is established for caproic acid, but general controls for corrosive irritants apply, emphasizing ventilation and skin protection. It is not classified as carcinogenic by the International Agency for Research on Cancer (IARC Group 3: not classifiable as to its carcinogenicity to humans).

Environmental impact

Caproic acid, also known as hexanoic acid, enters the environment primarily through industrial effluents from processes and oil processing activities. It has been detected in from organic waste treatment and , with concentrations reaching up to 12.6 g/L in fermentation broths before treatment, though environmental releases are typically lower, on the order of micrograms per liter in receiving waters. Caproic acid is readily biodegradable under aerobic conditions, achieving 87% degradation in 20 days in screening tests with , meeting the criteria for ready biodegradability (e.g., >60% in 28 days per 301 guidelines). Its in and is estimated at 1–4 weeks, driven by microbial degradation, with high mobility in (Koc 24–37) and minimal adsorption to sediments. Under anaerobic conditions, it is also metabolized, supporting its fate in digesters and sediments. Ecotoxicity of caproic acid to aquatic life is low, with LC50 values for fish (e.g., bluegill sunfish) ranging from 88 to >150 mg/L (96 h) and EC50 for invertebrates (e.g., ) at 22–72 mg/L (48 h); data for indicate similar low acute effects, with no growth inhibition below 100 mg/L in related studies. It shows no significant potential, with an estimated factor (BCF) of 3. Caproic acid is registered under the REACH regulation and is not classified as persistent, bioaccumulative, or toxic (PBT), nor is it listed as a under the Stockholm Convention, due to its rapid degradation and low bioaccumulation. Environmental releases can be mitigated through treatment in anaerobic digesters, where caproic acid is effectively degraded or even produced as part of chain elongation processes from organic waste. Emerging biotechnological production methods via from renewable feedstocks further reduce the petrochemical-derived environmental footprint compared to traditional synthesis.

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