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Record Information
Creation Date2009-07-30 17:56:54 UTC
Update Date2014-12-24 20:26:01 UTC
Accession NumberT3D3268
Common NameAcetic acid
ClassSmall Molecule
DescriptionAcetic acid is one of the simplest carboxylic acids. It is an important chemical reagent and industrial chemical that is used in the production of plastic soft drink bottles, photographic film; and polyvinyl acetate for wood glue, as well as many synthetic fibres and fabrics. Acetic acid can be very corrosive, depending on the concentration. It is one ingredient of cigarette. In households diluted acetic acid is often used as a cleaning agent. In the food industry acetic acid is used as an acidity regulator. The acetyl group, derived from acetic acid, is fundamental to the biochemistry of virtually all forms of life. When bound to coenzyme A it is central to the metabolism of carbohydrates and fats. However, the concentration of free acetic acid in cells is kept at a low level to avoid disrupting the control of the pH of the cell contents. Acetic acid is produced and excreted by certain bacteria, notably the Acetobacter genus and Clostridium acetobutylicum. These bacteria are found universally in foodstuffs, water, and soil, and acetic acid is produced naturally as fruits and some other foods spoil. Acetic acid is also a component of the vaginal lubrication of humans and other primates, where it appears to serve as a mild antibacterial agent.
Compound Type
  • Anti-Bacterial Agent
  • Bacterial Toxin
  • Cigarette Toxin
  • Cosmetic Toxin
  • Drug
  • Food Toxin
  • Fragrance Toxin
  • Household Toxin
  • Indicator and Reagent
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pesticide
Chemical Structure
Acetic acid, ion(1-)
Ethanoic acid
Ethylic acid
Glacial acetate
Glacial acetic acid
Kyselina octova
MeCO2 anion
Methanecarboxylic acid
Vinegar acid
Chemical FormulaC2H3O2
Average Molecular Mass59.045 g/mol
Monoisotopic Mass59.014 g/mol
CAS Registry Number64-19-7
IUPAC Nameacetate
Traditional Nameacetate
InChI IdentifierInChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)/p-1
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Golgi apparatus
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
  • Most Tissues
Amino Sugar MetabolismSMP00045 map00520
Ethanol DegradationSMP00449 Not Available
Fatty Acid BiosynthesisSMP00456 map00061
Pyruvate MetabolismSMP00060 map00620
Biological Roles
Chemical Roles
Physical Properties
AppearanceColorless liquid.
Experimental Properties
Melting Point16.6°C
Boiling Point117.9°C
Solubility1E+006 mg/L (at 25°C)
Predicted Properties
Water Solubility490 g/LALOGPS
pKa (Strongest Acidic)4.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.48 m³·mol⁻¹ChemAxon
Polarizability4.96 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-f5685ebb25f1bef6afeaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-f6251d3582ace30e2babJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-9000000000-7848c7adcde448d800acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-0828d9d6bd37d8a55106JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-97ec887bce4752e1c84dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-22e58030e49b08ff4d50JSpectraViewer
Toxicity Profile
Route of ExposureOral (21) ; ihalation (21) ; ingestion (21)
Mechanism of ToxicityAcetic acid is toxic due to its corrosive nature. In addition to causing skin burns and irritation to the mucous membranes, ingestion can result in severe damage to the digestive system and a potentially lethal change in the acidity of the blood. (20)
MetabolismAcetic acid is is absorbed from the gastrointestinal tract and through the lungs. It is completely oxidized by the tissues, with metabolism involving the formation of ketone bodies. The products of acetic acid are used in the formation of glycogen, as intermediates of carbohydrates and fatty acid synthesis, and in cholesterol synthesis. In addition, acetic acid participates in the acetylation of amines and formation of proteins of plasma, liver, kidney, gut mucosa, muscle, and brain. (21)
Toxicity ValuesLD50: 3.53 g/kg (Oral, Rat) (17) LD50: 525 mg/kg (Intravenous, Mouse) (16) LD50: 1060 mg/kg (Dermal, Rabbit) (16) LC50: 5620 ppm over 1 hour (Inhalation, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAcetic acid gives vinegar its sour taste and pungent smell. It is an important chemical reagent and industrial chemical, used in the plastic, pharmaceutical, dye, insecticide, textile, rubber, and photographic industries. Water-free acetic acid (glacial acetic acid) is used in the production of certain fragrances. (20) Used to treat infections in the ear canal.
Minimum Risk LevelNot Available
Health EffectsConcentrated acetic acid is corrosive and can cause skin burns, permanent eye damage, and irritation to the mucous membranes. Ingestion can cause severe damage to the digestive system and a potentially lethal change in the acidity of the blood. (20)
SymptomsAcetic acid is corrosive and can cause skin burns and irritation to the mucous membranes. These burns or blisters may not appear until hours after exposure. (20)
TreatmentIn cases of skin or eye exposure, the area should be flushed with water and burns covered with dry, sterile dressings after decontamination. If ingested, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution. Watch for signs of respiratory insufficiency and assist respiration if necessary. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03166
PubChem Compound ID176
ChemSpider ID171
UniProt IDNot Available
OMIM ID276100 , 601705
ChEBI ID30089
CTD IDNot Available
Stitch IDAcetic acid
ACToR ID3254
Wikipedia LinkAcetic_acid
Synthesis Reference

Earl M. Chamberlin, Warren K. Russ, Jr., George G. Hazen, “Process for preparing [1-oxo-2-cyclopentyl (or 2-isopropyl)-2-methyl-6,7-dichloro-5-indanyloxy] acetic acid.” U.S. Patent US3950408, issued April, 1928.

General References
  1. Skouby AP, Hippe E, Olesen H: Antibody to transcobalamin II and B12 binding capacity in patients treated with hydroxocobalamin. Blood. 1971 Dec;38(6):769-74. [5126165 ]
  2. Gidlof AC, Ocaya P, Olofsson PS, Torma H, Sirsjo A: Differences in retinol metabolism and proliferative response between neointimal and medial smooth muscle cells. J Vasc Res. 2006;43(4):392-8. Epub 2006 Jul 6. [16837774 ]
  3. Muniz-Junqueira MI, Braga Lopes C, Magalhaes CA, Schleicher CC, Veiga JP: Acute and chronic influence of hemodialysis according to the membrane used on phagocytic function of neutrophils and monocytes and pro-inflammatory cytokines production in chronic renal failure patients. Life Sci. 2005 Nov 4;77(25):3141-55. Epub 2005 Jul 11. [16005905 ]
  4. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [12097436 ]
  5. Sugawara G, Nagino M, Nishio H, Ebata T, Takagi K, Asahara T, Nomoto K, Nimura Y: Perioperative synbiotic treatment to prevent postoperative infectious complications in biliary cancer surgery: a randomized controlled trial. Ann Surg. 2006 Nov;244(5):706-14. [17060763 ]
  6. Camoutsis C, Trafalis D, Pairas G, Papageorgiou A: On the formation of 4-[N,N-bis(2-chloroethyl)amino]phenyl acetic acid esters of hecogenin and aza-homo-hecogenin and their antileukemic activity. Farmaco. 2005 Oct;60(10):826-9. Epub 2005 Aug 31. [16139280 ]
  7. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. [15627241 ]
  8. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [7762816 ]
  9. Li M, Pan XL, Wang LL, Feng Y, Huang N, Wu Q, Li X, Wang BY: [Study of antmicrobial mechanisms of human cervical mucus: isolation and characterization of antibacterial polypeptides]. Zhonghua Yi Xue Za Zhi. 2005 Apr 27;85(16):1109-12. [16029568 ]
  10. Vaca G, Hernandez A, Ibarra B, Velazquez A, Olivares N, Sanchez-Corona J, Medina C, Cantu JM: Detection of inborn errors of metabolism in 1,117 patients studied because of suspected inherited disease. Arch Invest Med (Mex). 1981;12(3):341-8. [7294941 ]
  11. Commodari F, Arnold DL, Sanctuary BC, Shoubridge EA: 1H NMR characterization of normal human cerebrospinal fluid and the detection of methylmalonic acid in a vitamin B12 deficient patient. NMR Biomed. 1991 Aug;4(4):192-200. [1931558 ]
  12. Yagi K, Nakamura A, Sekine A: [Magnification endoscopy diagnosis of Barrett's esophagus with methylene blue and acetic acid]. Nihon Rinsho. 2005 Aug;63(8):1411-5. [16101231 ]
  13. Fan DD, Luo Y, Mi Y, Ma XX, Shang L: Characteristics of fed-batch cultures of recombinant Escherichia coli containing human-like collagen cDNA at different specific growth rates. Biotechnol Lett. 2005 Jun;27(12):865-70. [16086249 ]
  14. Syrjanen K, Naud P, Derchain S, Roteli-Martins C, Longatto-Filho A, Tatti S, Branca M, Erzen M, Hammes LS, Matos J, Gontijo R, Sarian L, Braganca J, Arlindo FC, Maeda MY, Lorincz A, Dores GB, Costa S, Syrjanen S: Comparing PAP smear cytology, aided visual inspection, screening colposcopy, cervicography and HPV testing as optional screening tools in Latin America. Study design and baseline data of the LAMS study. Anticancer Res. 2005 Sep-Oct;25(5):3469-80. [16101165 ]
  15. Yri OE, Bjoro T, Fossa SD: Failure to achieve castration levels in patients using leuprolide acetate in locally advanced prostate cancer. Eur Urol. 2006 Jan;49(1):54-8; discussion 58. Epub 2005 Nov 15. [16314038 ]
  16. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  17. O'Neil MJ (ed) (2001). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc.
  18. Bronstein, AC, Currance PL (1994). Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994.
  19. EPA/Office of Pollution Prevention and Toxics (2003). High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans.
  20. Wikipedia. Acetic Acid. Last Updated 14 November 2009. [Link]
  21. Food and Agriculture Organization of the United Nations/World Health Organization (1967).Tenth Report of the Joint FAO/WHO Expert Committee on Food Additives, FAO Nutrition Meetings Report Series. [Link]
  22. eMedicine [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available


General Function:
Lipid binding
Specific Function:
G protein-coupled receptor that is activated by a major product of dietary fiber digestion, the short chain fatty acids (SCFAs), and that plays a role in the regulation of whole-body energy homeostasis and in intestinal immunity. In omnivorous mammals, the short chain fatty acids acetate, propionate and butyrate are produced primarily by the gut microbiome that metabolizes dietary fibers. SCFAs serve as a source of energy but also act as signaling molecules. That G protein-coupled receptor is probably coupled to the pertussis toxin-sensitive, G(i/o)-alpha family of G proteins but also to the Gq family (PubMed:12496283, PubMed:12711604, PubMed:23589301). Its activation results in the formation of inositol 1,4,5-trisphosphate, the mobilization of intracellular calcium, the phosphorylation of the MAPK3/ERK1 and MAPK1/ERK2 kinases and the inhibition of intracellular cAMP accumulation. May play a role in glucose homeostasis by regulating the secretion of GLP-1, in response to short-chain fatty acids accumulating in the intestine. May also regulate the production of LEP/Leptin, a hormone acting on the central nervous system to inhibit food intake. Finally, may also regulate whole-body energy homeostasis through adipogenesis regulating both differentiation and lipid storage of adipocytes. In parallel to its role in energy homeostasis, may also mediate the activation of the inflammatory and immune responses by SCFA in the intestine, regulating the rapid production of chemokines and cytokines. May also play a role in the resolution of the inflammatory response and control chemotaxis in neutrophils. In addition to SCFAs, may also be activated by the extracellular lectin FCN1 in a process leading to activation of monocytes and inducing the secretion of interleukin-8/IL-8 in response to the presence of microbes (PubMed:21037097). Among SCFAs, the fatty acids containing less than 6 carbons, the most potent activators are probably acetate, propionate and butyrate (PubMed:12496283, PubMed:12711604). Exhibits a SCFA-independent constitutive G protein-coupled receptor activity (PubMed:23066016).
Gene Name:
Uniprot ID:
Molecular Weight:
37143.375 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50120 uMNot AvailableBindingDB 50074329
  1. Wang Y, Jiao X, Kayser F, Liu J, Wang Z, Wanska M, Greenberg J, Weiszmann J, Ge H, Tian H, Wong S, Schwandner R, Lee T, Li Y: The first synthetic agonists of FFA2: Discovery and SAR of phenylacetamides as allosteric modulators. Bioorg Med Chem Lett. 2010 Jan 15;20(2):493-8. doi: 10.1016/j.bmcl.2009.11.112. Epub 2009 Nov 26. [20005104 ]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
Uniprot ID:
Molecular Weight:
127499.88 Da
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
General Function:
Protein tyrosine kinase activity
Specific Function:
Non-receptor tyrosine-protein kinase that plays a role in many biological processes including regulation of cell growth and survival, cell adhesion, integrin-mediated signaling, cytoskeletal remodeling, cell motility, immune response and axon guidance. Inactive FYN is phosphorylated on its C-terminal tail within the catalytic domain. Following activation by PKA, the protein subsequently associates with PTK2/FAK1, allowing PTK2/FAK1 phosphorylation, activation and targeting to focal adhesions. Involved in the regulation of cell adhesion and motility through phosphorylation of CTNNB1 (beta-catenin) and CTNND1 (delta-catenin). Regulates cytoskeletal remodeling by phosphorylating several proteins including the actin regulator WAS and the microtubule-associated proteins MAP2 and MAPT. Promotes cell survival by phosphorylating AGAP2/PIKE-A and preventing its apoptotic cleavage. Participates in signal transduction pathways that regulate the integrity of the glomerular slit diaphragm (an essential part of the glomerular filter of the kidney) by phosphorylating several slit diaphragm components including NPHS1, KIRREL and TRPC6. Plays a role in neural processes by phosphorylating DPYSL2, a multifunctional adapter protein within the central nervous system, ARHGAP32, a regulator for Rho family GTPases implicated in various neural functions, and SNCA, a small pre-synaptic protein. Participates in the downstream signaling pathways that lead to T-cell differentiation and proliferation following T-cell receptor (TCR) stimulation. Also participates in negative feedback regulation of TCR signaling through phosphorylation of PAG1, thereby promoting interaction between PAG1 and CSK and recruitment of CSK to lipid rafts. CSK maintains LCK and FYN in an inactive form. Promotes CD28-induced phosphorylation of VAV1.
Gene Name:
Uniprot ID:
Molecular Weight:
60761.49 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Dissociation0.9 uMNot AvailableBindingDB 50074329
  1. Lee TR, Lawrence DS: Acquisition of high-affinity, SH2-targeted ligands via a spatially focused library. J Med Chem. 1999 Mar 11;42(5):784-7. [10072676 ]
General Function:
Sh2 domain binding
Specific Function:
Non-receptor tyrosine-protein kinase that plays an essential role in the selection and maturation of developing T-cells in the thymus and in the function of mature T-cells. Plays a key role in T-cell antigen receptor (TCR)-linked signal transduction pathways. Constitutively associated with the cytoplasmic portions of the CD4 and CD8 surface receptors. Association of the TCR with a peptide antigen-bound MHC complex facilitates the interaction of CD4 and CD8 with MHC class II and class I molecules, respectively, thereby recruiting the associated LCK protein to the vicinity of the TCR/CD3 complex. LCK then phosphorylates tyrosines residues within the immunoreceptor tyrosine-based activation motifs (ITAM) of the cytoplasmic tails of the TCR-gamma chains and CD3 subunits, initiating the TCR/CD3 signaling pathway. Once stimulated, the TCR recruits the tyrosine kinase ZAP70, that becomes phosphorylated and activated by LCK. Following this, a large number of signaling molecules are recruited, ultimately leading to lymphokine production. LCK also contributes to signaling by other receptor molecules. Associates directly with the cytoplasmic tail of CD2, which leads to hyperphosphorylation and activation of LCK. Also plays a role in the IL2 receptor-linked signaling pathway that controls the T-cell proliferative response. Binding of IL2 to its receptor results in increased activity of LCK. Is expressed at all stages of thymocyte development and is required for the regulation of maturation events that are governed by both pre-TCR and mature alpha beta TCR. Phosphorylates other substrates including RUNX3, PTK2B/PYK2, the microtubule-associated protein MAPT, RHOH or TYROBP.
Gene Name:
Uniprot ID:
Molecular Weight:
58000.15 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Dissociation0.64 uMNot AvailableBindingDB 50074329
Dissociation1.3 uMNot AvailableBindingDB 50074329
  1. Lee TR, Lawrence DS: Acquisition of high-affinity, SH2-targeted ligands via a spatially focused library. J Med Chem. 1999 Mar 11;42(5):784-7. [10072676 ]