Acetic acid

Relevant Data

Food Additives Approved in the United States:

Food Additives Approved by WHO:

Food Additives Approved by European Union:

  • Acetic acid [show]

General Information

Chemical nameAcetic acid
CAS number64-19-7
COE number2
JECFA number81
Flavouring typesubstances
FL No.08.002
MixtureNo
Purity of the named substance at least 95% unless otherwise specified
Reference bodyJECFA

From webgate.ec.europa.eu

Computed Descriptors

Download SDF
2D Structure
CID176
IUPAC Nameacetic acid
InChIInChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
InChI KeyQTBSBXVTEAMEQO-UHFFFAOYSA-N
Canonical SMILESCC(=O)O
Molecular FormulaC2H4O2
Wikipediaacetic acid

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight60.052
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Complexity31.0
CACTVS Substructure Key Fingerprint A A A D c Y B A M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A A A C A g A A C C A A A A g A I A A C Q C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area37.3
Monoisotopic Mass60.021
Exact Mass60.021
XLogP3None
XLogP3-AA-0.2
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count4
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9639
Human Intestinal AbsorptionHIA+0.9841
Caco-2 PermeabilityCaco2+0.5644
P-glycoprotein SubstrateNon-substrate0.8563
P-glycoprotein InhibitorNon-inhibitor0.9888
Non-inhibitor0.9904
Renal Organic Cation TransporterNon-inhibitor0.9472
Distribution
Subcellular localizationMitochondria0.6703
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7598
CYP450 2D6 SubstrateNon-substrate0.9517
CYP450 3A4 SubstrateNon-substrate0.8093
CYP450 1A2 InhibitorNon-inhibitor0.9406
CYP450 2C9 InhibitorNon-inhibitor0.9695
CYP450 2D6 InhibitorNon-inhibitor0.9729
CYP450 2C19 InhibitorNon-inhibitor0.9907
CYP450 3A4 InhibitorNon-inhibitor0.9827
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9930
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9770
Non-inhibitor0.9876
AMES ToxicityNon AMES toxic0.9815
CarcinogensCarcinogens 0.6452
Fish ToxicityLow FHMT0.6462
Tetrahymena Pyriformis ToxicityLow TPT0.9428
Honey Bee ToxicityHigh HBT0.7866
BiodegradationReady biodegradable0.9069
Acute Oral ToxicityIII0.7890
Carcinogenicity (Three-class)Non-required0.7376

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility0.5496LogS
Caco-2 Permeability1.2846LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5735LD50, mol/kg
Fish Toxicity3.1825pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.3761pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureOral ; ihalation ; ingestion
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.
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.
Toxicity ValuesLD50: 3.53 g/kg (Oral, Rat) LD50: 525 mg/kg (Intravenous, Mouse) LD50: 1060 mg/kg (Dermal, Rabbit) LC50: 5620 ppm over 1 hour (Inhalation, Mouse)
Lethal Dose
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level
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. (L1885)
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.
Reference
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  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 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassCarboxylic acids
Intermediate Tree NodesNot available
Direct ParentCarboxylic acids
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsMonocarboxylic acid or derivatives - Carboxylic acid - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.

From ClassyFire

Targets

Target Details

Tyrosine-protein kinase Fyn

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:
FYN
Uniprot ID:
P06241
Molecular Weight:
60761.49 Da
References
  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 ]
Target Details

Free fatty acid receptor 2

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:
FFAR2
Uniprot ID:
O15552
Molecular Weight:
37143.375 Da
References
  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 ]
Target Details

Transient receptor potential cation channel subfamily A member 1

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:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  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 ]
Target Details

Tyrosine-protein kinase Lck

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:
LCK
Uniprot ID:
P06239
Molecular Weight:
58000.15 Da
References
  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 ]

From T3DB