Record Information |
---|
Version | 2.0 |
---|
Created at | 2005-11-16 15:48:42 UTC |
---|
Updated at | 2021-08-19 23:58:49 UTC |
---|
NP-MRD ID | NP0001129 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Acetoacetic acid |
---|
Description | Acetoacetic acid (AcAc) is a weak organic acid that can be produced in the human liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis). It is then partially converted into acetone by decarboxylation and excreted either in urine or through respiration. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first two weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies are utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life (PMID: 3884391 ). The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected. |
---|
Structure | InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7) |
---|
Synonyms | Value | Source |
---|
3-Ketobutanoic acid | ChEBI | 3-Ketobutyric acid | ChEBI | 3-Oxobutanoic acid | ChEBI | 3-Oxobutyric acid | ChEBI | beta-Ketobutyric acid | ChEBI | 3-Ketobutanoate | Generator | 3-Ketobutyrate | Generator | 3-Oxobutanoate | Generator | 3-Oxobutyrate | Generator | b-Ketobutyrate | Generator | b-Ketobutyric acid | Generator | beta-Ketobutyrate | Generator | Β-ketobutyrate | Generator | Β-ketobutyric acid | Generator | Acetoacetate | Generator | 3-oxo-Butanoate | HMDB | 3-oxo-Butanoic acid | HMDB | Diacetate | HMDB | Diacetic acid | HMDB | Acetoacetic acid, sodium salt | HMDB | Acetoacetic acid, calcium salt | HMDB | Acetoacetic acid, lithium salt | HMDB | Oxobutyrate | HMDB | Sodium acetoacetate | HMDB |
|
---|
Chemical Formula | C4H6O3 |
---|
Average Mass | 102.0886 Da |
---|
Monoisotopic Mass | 102.03169 Da |
---|
IUPAC Name | 3-oxobutanoic acid |
---|
Traditional Name | acetoacetic acid |
---|
CAS Registry Number | 541-50-4 |
---|
SMILES | CC(=O)CC(O)=O |
---|
InChI Identifier | InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7) |
---|
InChI Key | WDJHALXBUFZDSR-UHFFFAOYSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-07-25 | View Spectrum |
| Species |
---|
Species of Origin | |
---|
Species Where Detected | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Keto acids and derivatives |
---|
Sub Class | Short-chain keto acids and derivatives |
---|
Direct Parent | Short-chain keto acids and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Short-chain keto acid
- Beta-keto acid
- 1,3-dicarbonyl compound
- Beta-hydroxy ketone
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | |
---|
Predicted Properties | |
---|
General References | - 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 ]
- Heller MJ, Adams PW, Orosz CG: Evaluation of an automated method of percent reactive antibody determination. Hum Immunol. 1992 Nov;35(3):179-87. [PubMed:1293081 ]
- Oligny LL, Lough J: Hepatic sinusoidal ectasia. Hum Pathol. 1992 Aug;23(8):953-6. [PubMed:1644440 ]
- Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. [PubMed:6696735 ]
- Galey JB, Destree O, Dumats J, Genard S, Tachon P: Protection against oxidative damage by iron chelators: effect of lipophilic analogues and prodrugs of N,N'-bis(3,4,5-trimethoxybenzyl)ethylenediamine- N,N'-diacetic acid (OR10141). J Med Chem. 2000 Apr 6;43(7):1418-21. [PubMed:10753479 ]
- Saibara T, Onishi S, Sone J, Yamamoto N, Shimahara Y, Mori K, Ozawa K, Yamamoto Y: Arterial ketone body ratio as a possible indicator for liver transplantation in fulminant hepatic failure. Transplantation. 1991 Apr;51(4):782-6. [PubMed:2014530 ]
- Mahowald ML, Handwerger BS, Capertone EM Jr, Douglas SD: A comparative study of procedures for sheep erythrocyte-human-T-lymphocyte rosette formation. J Immunol Methods. 1977;15(3):239-45. [PubMed:404361 ]
- Sato T, Oouchi M, Nagakubo H, Chiba T, Ogawa S, Sato C, Sugimura K, Fukuda M: Effect of pravastatin on plasma ketone bodies in diabetics with hypercholesterolemia. Tohoku J Exp Med. 1998 May;185(1):25-9. [PubMed:9710942 ]
- Krejsa CM, Schieven GL: Detection of oxidative stress in lymphocytes using dichlorodihydrofluorescein diacetate. Methods Mol Biol. 2000;99:35-47. [PubMed:10909075 ]
- Fritzsche I, Buhrdel P, Melcher R, Bohme HJ: Stability of ketone bodies in serum in dependence on storage time and storage temperature. Clin Lab. 2001;47(7-8):399-403. [PubMed:11499803 ]
- Polsky-Fisher SL, Cao H, Lu P, Gibson CR: Effect of cytochromes P450 chemical inhibitors and monoclonal antibodies on human liver microsomal esterase activity. Drug Metab Dispos. 2006 Aug;34(8):1361-6. Epub 2006 May 23. [PubMed:16720683 ]
- Fulop M, Murthy V, Michilli A, Nalamati J, Qian Q, Saitowitz A: Serum beta-hydroxybutyrate measurement in patients with uncontrolled diabetes mellitus. Arch Intern Med. 1999 Feb 22;159(4):381-4. [PubMed:10030312 ]
- Tanaka Y, Ohdan H, Onoe T, Mitsuta H, Tashiro H, Itamoto T, Asahara T: Low incidence of acute rejection after living-donor liver transplantation: immunologic analyses by mixed lymphocyte reaction using a carboxyfluorescein diacetate succinimidyl ester labeling technique. Transplantation. 2005 May 15;79(9):1262-7. [PubMed:15880082 ]
- de Araujo Burgos MG, Bion FM, Campos F: [Lactation and alcohol: clinical and nutritional effects]. Arch Latinoam Nutr. 2004 Mar;54(1):25-35. [PubMed:15332353 ]
- Walker V, Mills GA, Mellor JM, Langley GJ, Farrant RD: A novel pyrroline-5-carboxylic acid and acetoacetic acid adduct in hyperprolinaemia type II. Clin Chim Acta. 2003 May;331(1-2):7-17. [PubMed:12691858 ]
- Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. [PubMed:3884391 ]
|
---|