| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-05-15 12:56:53 -0600 |
| HMDB ID |
HMDB00042 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Acetic acid |
| Description |
Acetic 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. 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Acetate
- Ethanoate
- Ethanoic acid
- Ethylate
- Ethylic acid
- Glacial acetate
- Glacial acetic acid
- Kyselina octova
- Methanecarboxylate
- Methanecarboxylic acid
- Vinegar
- Vinegar acid
|
| Chemical Formula |
C2H4O2 |
| Average Molecular Weight |
60.052 |
| Monoisotopic Molecular Weight |
60.021129372 |
| IUPAC Name |
acetic acid |
| Traditional IUPAC Name |
acetic acid |
| CAS Registry Number |
64-19-7 |
| SMILES |
CC(O)=O |
| InChI Identifier |
InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4) |
| InChI Key |
QTBSBXVTEAMEQO-UHFFFAOYSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Organic Acids and Derivatives |
| Class |
Carboxylic Acids and Derivatives |
| Sub Class |
Carboxylic Acid Derivatives |
| Other Descriptors |
- Aliphatic Acyclic Compounds
- Saturated fatty acids(KEGG)
- Straight chain fatty acids(KEGG)
- Straight chain fatty acids(Lipidmaps)
- monocarboxylic acid(ChEBI)
|
| Substituents |
|
| Direct Parent |
Carboxylic Acids |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Glycerophospholipid metabolism
- Component of Propanoate metabolism
- Component of Pyruvate metabolism
|
| Application |
Not Available |
| Cellular locations |
- Extracellular
- Mitochondria
- Golgi apparatus
|
| Physical Properties |
| State |
Liquid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
16.6 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
1000.0 mg/mL |
Not Available |
| LogP |
-0.17 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|
|
| Biological Properties |
| Cellular Locations |
- Extracellular
- Mitochondria
- Golgi apparatus
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Saliva
- Urine
|
| Tissue Location |
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
30.4 (22.0-40.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
41.9 +/- 15.1 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
116.0 +/- 55.0 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
58.0 +/- 27.0 uM |
Not Specified |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
100.0 +/- 30.0 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
284.0 +/- 126.0 uM |
Children (1-13 year old) |
Both |
Normal |
Not Available |
| Saliva |
Detected and Quantified |
|
433 (19-2749) uM |
Adult (>18 years old) |
Male |
normal |
At rest without stimulation
|
| Saliva |
Detected and Quantified |
|
112 (5-726) uM |
Adult (>18 years old) |
Male |
normal |
Salivary induction with a citric acid solution...
|
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
13.0 (2.5-106.0) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
urine by NMR
|
| Urine |
Detected and Quantified |
|
3.31 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
45.33 +/- 53.33 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
42.2 +/- 17.3 uM |
Adult (>18 years old) |
Not Specified |
Heart Transplant |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
35.3 - 211.7 uM |
Adult (>18 years old) |
Not Specified |
Multiple sclerosis |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Breast cancer |
Not Available |
| Urine |
Detected and Quantified |
|
53.0 +/- 71.0 umol/mmol creatinine |
Not Specified |
Both |
Lung cancer |
Not Available |
| Urine |
Detected and Quantified |
|
23.7 +/- 4.5 umol/mmol creatinine |
Adult (>18 years old) |
Both |
3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency |
Not Available |
| Urine |
Detected and Quantified |
|
12.9 +/- 0 umol/mmol creatinine |
Adult (>18 years old) |
Both |
3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency |
Not Available |
| Urine |
Detected and Quantified |
|
54.1 +/- 23.8 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Arginosuccinic aciduria |
Not Available |
| Urine |
Detected and Quantified |
|
20.2 +/- 3.9 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Propionic acidemia |
Not Available |
| Urine |
Detected and Quantified |
|
20.8 +/- 3 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Propionic acidemia |
Not Available |
| Urine |
Detected and Quantified |
|
99.4 +/- 8.6 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Tyrosinemia I |
Not Available |
| Urine |
Detected and Quantified |
|
16.3 +/- 7.1 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Phenylketonuria |
Not Available |
| Urine |
Detected and Quantified |
|
375.3 +/- 6.3 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Phenylketonuria |
Not Available |
| Urine |
Detected and Quantified |
|
13.2 +/- 5.5 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Maple syrup urine disease |
Not Available |
| Urine |
Detected and Quantified |
|
21.8 +/- 0 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Aminoaciduria |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| Multiple sclerosis |
- Lutz NW, Viola A, Malikova I, Confort-Gouny S, Audoin B, Ranjeva JP, Pelletier J, Cozzone PJ: Inflammatory multiple-sclerosis plaques generate characteristic metabolic profiles in cerebrospinal fluid. PLoS ONE. 2007 Jul 4;2(7):e595.
Pubmed: 17611627
|
| Lung Cancer |
- Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25.
Pubmed: 18953024
|
|
| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
DB03166  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB008299 |
| KNApSAcK ID |
C00001176  |
| Chemspider ID |
171  |
| KEGG Compound ID |
C00033  |
| BioCyc ID |
ACET  |
| BiGG ID |
33590  |
| Wikipedia Link |
Acetic acid  |
| NuGOwiki Link |
HMDB00042  |
| Metagene Link |
HMDB00042  |
| METLIN ID |
3206  |
| PubChem Compound |
176  |
| PDB ID |
ACY  |
| ChEBI ID |
15366  |
| References |
| Synthesis Reference |
Law, David John. Process for the preparation of carboxylic acids and/or derivatives thereof. PCT Int. Appl. (2007), 14pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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.
Pubmed: 16005905
- 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.
Pubmed: 12097436
- 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.
Pubmed: 17060763
- 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.
Pubmed: 16139280
- 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.
Pubmed: 15627241
- 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.
Pubmed: 7762816
- 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.
Pubmed: 16029568
- 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.
Pubmed: 7294941
- 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.
Pubmed: 1931558
- Yagi K, Nakamura A, Sekine A: [Magnification endoscopy diagnosis of Barrett's esophagus with methylene blue and acetic acid] Nippon Rinsho. 2005 Aug;63(8):1411-5.
Pubmed: 16101231
- 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.
Pubmed: 16086249
- 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.
Pubmed: 16101165
- 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.
Pubmed: 16314038
|
| Enzymes |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
| Name: |
Sialate O-acetylesterase
|
| Reactions: |
- N-acetyl-O-acetylneuraminate + H2O = N-acetylneuraminate + acetate [RN:R01810]
|
| Gene Name: |
SIAE |
| Uniprot ID: |
Q9HAT2  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
| Name: |
Acylphosphatase-2
|
| Reactions: |
- an acylphosphate + H2O = a carboxylate + phosphate [RN:R00539]
|
| Gene Name: |
ACYP2 |
| Uniprot ID: |
P14621  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Acylphosphatase-1
|
| Reactions: |
- an acylphosphate + H2O = a carboxylate + phosphate [RN:R00539]
|
| Gene Name: |
ACYP1 |
| Uniprot ID: |
P07311  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Aminoacylase-1
|
| Reactions: |
- an N-acyl-L-amino acid + H2O = a carboxylate + an L-amino acid [RN:R01263]
|
| Gene Name: |
ACY1 |
| Uniprot ID: |
Q03154  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Aspartoacylase
|
| Reactions: |
- N-acyl-L-aspartate + H2O = a carboxylate + L-aspartate [RN:R00546]
|
| Gene Name: |
ASPA |
| Uniprot ID: |
P45381  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|