Butyric acid (CED0001166)

Record Information
Version1.0
Creation Date2014-09-05 17:11:48 UTC
Update Date2026-05-14 17:50:40 UTC
Accession NumberCHEM003552
Identification
Common NameButyric acid
ClassSmall Molecule
Description
Butyric acid (C4H8O2) is an endogenous liquid with an average molecular weight of 88.11 g/mol. Butyric acid belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. This compound is detected in various tissues, including the intestine, large intestine, kidney, muscle, neuron, prostate, and fibroblasts. It interacts with ten recorded protein targets, including cholinesterase (BCHE), histone deacetylase 1 (HDAC1), histone deacetylase 3 (HDAC3), and histone deacetylase 4 (HDAC4). Regarding health effects, butyric acid is associated with a decrease in inflammation (PMC11643819) and has a therapeutic effect on inflammation (PMC8145417). Industrially, butyric acid is utilized as a pH regulating agent, deodorizer, fragrance, and flavouring and nutrient. It also serves as an antioxidant in both biological and industrial contexts (PMC10778838). The compound is used in low-density polyethylene and high-density polyethylene plastics, and it is released from poly(methyl methacrylate), ethylene-vinyl acetate, and polypropylene. Its presence in ethylene vinyl alcohol remains inconclusive. Butyric acid is found in 46 recorded sources, including food contact materials, fermentation processes for beer, food preservation, and the preparation of malt, as well as household cleaning and consumer products such as bleaching agents, perfumes within detergents and soaps, and smoking requisites. It is also found in building and construction materials, including floors, ceilings, stairs, and ramps, and in electrical and electronic equipment such as communication cables, antennas, and conductive bodies. Recorded exposure routes include oral, inhalation, and touch.
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
SynonymsNot Available
Chemical FormulaC4H8O2
Average Molecular Mass88.105 g/mol
Monoisotopic Mass88.052 g/mol
CAS Registry Number107-92-6
IUPAC Namebutanoic acid
Traditional Namebutyric acid
SMILESCCCC(O)=O
InChI IdentifierInChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
InChI KeyFERIUCNNQQJTOY-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Intestine
  • Kidney
  • Large Intestine
  • Muscle
  • Neuron
  • Prostate
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-5.7°C
Boiling Point163.7°C
Solubility6E+004 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility239 g/LALOGPS
logP0.78ALOGPS
logP0.92ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity21.87 m³·mol⁻¹ChemAxon
Polarizability9.22 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-03dl-9000000000-032fc35b394786b5896aNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-03dl-9000000000-032fc35b394786b5896aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-002f-9000000000-a7792b54320e7c859731Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00fr-9100000000-d125b331c4a6d37648a1Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-7f461db56bfd8568ec71Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-66f857fa612f773837bcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-e6689b2e6bf21570b934Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-9000000000-b2ffa7d67b2466dea94fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-9000000000-7467bf19c64fd3f51105Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-9ae015043b014b3c93d9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-e30b3c6bd6218b9b49e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-efbb0e35a19a1713240bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-9ae015043b014b3c93d9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-e30b3c6bd6218b9b49e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-9000000000-efbb0e35a19a1713240bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-acb5cf0017a9ee680dd8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-9000000000-812e24462a71dccb0fecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-f9d30338ca1ee9409964Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9000000000-9d749b6b6cf2f93a8f85Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ku-9000000000-ee742730266fb4997777Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-88fc445cddcb726e93d8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9000000000-4b3590a18d40d4d58a01Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-9000000000-140190568a3f2b3c6f01Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9000000000-1f7dab1fbd0179ef6d17Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-9000000000-020fcfb652dc5a6f3036Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-3e4b1bc1291a3fbf86c9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-1f57e9adb6de1499caf5Not AvailableView Spectrum
MSMS Spectrumsplash10-03di-9000000000-5338ff8a9c4e59150abaNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityButyric acid is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsSymptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.
TreatmentIf the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2575.0Log mg/kg[1400:4600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationhas_therapeutic_effect_onNot AvailablePMC8145417
inflammationassociated_withdecreasePMC11643819
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
543Cellar ToolsFood, food processing & cookwareNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
639Degreasing LeatherTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
648Nitro DyesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)4.5931
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)5.91654
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)6.53933
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)3.81461
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)13.5458
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)12.4559
G-protein coupled receptor 84 structureClick to view 3D structureG-protein coupled receptor 84Q9NQS5HumansPredicted (SEA)2.41333
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)0.389246
Fatty acid-binding protein, adipocyte structureClick to view 3D structureFatty acid-binding protein, adipocyteP15090HumansPredicted (SEA)2.17978
Lysine-specific demethylase 2A structureClick to view 3D structureLysine-specific demethylase 2AQ9Y2K7HumansPredicted (SEA)1.94623
Histone lysine demethylase PHF8 structureClick to view 3D structureHistone lysine demethylase PHF8Q9UPP1HumansPredicted (SEA)0.155698
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)15.6477
Egl nine homolog 1 structureClick to view 3D structureEgl nine homolog 1Q9GZT9HumansPredicted (SEA)7.70707
Free fatty acid receptor 4 structureClick to view 3D structureFree fatty acid receptor 4Q5NUL3HumansPredicted (SEA)12.1445
Olfactory receptor 51E2 structureClick to view 3D structureOlfactory receptor 51E2Q9H255HumansPredicted (SEA)0.233548
Click to view 3D structureSuccinate receptor 1Q99MT6Mus musculusPredicted (SEA)0.155698
Click to view 3D structureOxoeicosanoid receptor 1Q8TDS5HumansPredicted (SEA)2.02408
Lysine-specific demethylase 5C structureClick to view 3D structureLysine-specific demethylase 5CP41229HumansPredicted (SEA)4.7488
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)75.358
Toll-like receptor 2 structureClick to view 3D structureToll-like receptor 2O60603HumansPredicted (SEA)2.02408
Click to view 3D structureN-acetylaspartylglutamate synthase AQ8IXN7HumansPredicted (SEA)4.51525
Gamma-glutamyl hydrolase structureClick to view 3D structureGamma-glutamyl hydrolaseQ92820HumansPredicted (SEA)2.33548
Click to view 3D structurePutative inactive group IIC secretory phospholipase A2Q5R387HumansPredicted (SEA)3.50322
Click to view 3D structureCAI-1 autoinducer sensor kinase/phosphatase CqsSQ9KM66Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)Predicted (SEA)4.28171
Fatty acid-binding protein 5 structureClick to view 3D structureFatty acid-binding protein 5Q01469HumansPredicted (SEA)1.63483
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansKnownNot Available
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansKnownNot Available
Histone deacetylase 3 structureClick to view 3D structureHistone deacetylase 3O15379HumansKnownNot Available
Histone deacetylase 4 structureClick to view 3D structureHistone deacetylase 4P56524HumansKnownNot Available
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansKnownNot Available
Histone deacetylase 7 structureClick to view 3D structureHistone deacetylase 7Q8WUI4HumansKnownNot Available
Histone deacetylase 9 structureClick to view 3D structureHistone deacetylase 9Q9UKV0HumansKnownNot Available
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansKnownNot Available
Concentrations
Not Available
External Links
IdentifiersNot Available
References
Synthesis Reference

Haruhiko Kikuchi, “Process for preparing 4-(4-biphenylyl)-4-oxo-butanoic acid.” U.S. Patent US4621154, issued November, 1977.

MSDSLink
General ReferencesNot Available