- 関
- acetoacetate
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/04/22 21:54:52」(JST)
[Wiki en表示]
| Acetoacetic acid |
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|
IUPAC name
3-oxobutanoic acid, diacetic acid
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| Identifiers |
| CAS number |
541-50-4 Y |
| PubChem |
96 |
| ChemSpider |
94 Y |
| DrugBank |
DB04025 |
| KEGG |
C00164 Y |
| ChEBI |
CHEBI:15344 Y |
| ChEMBL |
CHEMBL1230762 N |
| Jmol-3D images |
Image 1 |
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-
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7) Y
Key: WDJHALXBUFZDSR-UHFFFAOYSA-N Y
InChI=1/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
Key: WDJHALXBUFZDSR-UHFFFAOYAH
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| Properties |
| Molecular formula |
C4H6O3 |
| Molar mass |
102.09 g/mol |
| Melting point |
36.5 °C
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| Boiling point |
Decomposes
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| Acidity (pKa) |
3.58 [1] |
N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
Acetoacetic acid (also called diacetic acid) is the organic compound with the formula CH3COCH2COOH. It is the simplest beta-keto acid group and like other members of this class is unstable. The methyl and ethyl esters, which are quite stable, are produced on a large scale industrially as precursors to dyes.[2]
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Contents
- 1 Synthesis and properties
- 2 Detection
- 3 See also
- 4 References
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Synthesis and properties
In general, the esters are prepared by from diketene by treatment with alcohols.[2] Acetoacetic acid can be prepared by the hydrolysis of the ethyl acetoacetate followed by acidification of the anion.[3] In general, acetoacetic acid is generated at 0 °C and used in situ immediately.[4] It decomposes at a moderate rate to acetone and carbon dioxide:
- CH3C(O)CH2CO2H → CH3C(O)CH3 + CO2
The acid form has a half-life of 140 minutes at 37 °C in water, whereas the basic form (the anion) has a half-life of 130 hours. That is, it reacts about 50 times more slowly.[5]
It is a weak acid (like most alkyl carboxylic acids) with a pKa of 3.77.
Detection
When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid (BHB), and acetone, is what is detected. This is done using dipsticks coated in nitroprusside or similar reagents. Nitroprusside changes from pink to purple in the presence of acetoacetate, the conjugate base of acetoacetic acid, and the colour change is graded by eye. The popular dipstick used to detect ketone bodies in urine "Ketostix" by Bayer, only detects acetoacetate, not BHB or acetone.[citation needed]
See also
- 3-hydroxybutyrate dehydrogenase
References
- ^ Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
- ^ a b Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a18 313
- ^ Robert C. Krueger (1952). "Crystalline Acetoacetic Acid". Journal of the American Chemical Society 74 (21): 5536–5536. doi:10.1021/ja01141a521.
- ^ George A. Reynolds and J. A. VanAllan "Methylglyoxal-ω-Phenylhydrazone" Organic Syntheses, Collected Volume 4, p.633 (1963).http://www.orgsyn.org/orgsyn/pdfs/CV4P0633.pdf
- ^ Hay, R. W.; Bond, M. A. (1967). "Kinetics of decarboxilation of acetoacetic acid". Aust. J. Chem. 20 (9): 1823–8. doi:10.1071/CH9671823.
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Cholesterol and steroid metabolic intermediates
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|
| Mevalonate pathway |
| to HMG-CoA |
- Acetyl-CoA
- Acetoacetyl-CoA
- HMG-CoA
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|
| Ketone bodies |
- Acetone
- Acetoacetic acid
- beta-Hydroxybutyric acid
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|
| to DMAPP |
- Mevalonic acid
- Phosphomevalonic acid
- 5-Diphosphomevalonic acid
- Isopentenyl pyrophosphate
- Dimethylallyl pyrophosphate
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|
| Geranyl- |
- Geranyl pyrophosphate
- Geranylgeranyl pyrophosphate
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| Carotenoid |
- Prephytoene diphosphate
- Phytoene
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| Non-mevalonate pathway |
- DOXP
- MEP
- CDP-ME
- CDP-MEP
- MEcPP
- HMB-PP
- IPP
- DMAPP
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|
|
| To Cholesterol |
- Farnesyl pyrophosphate
- Squalene
- 2,3-Oxidosqualene
- Lanosterol
- Lanosterol
- Lathosterol
- 7-Dehydrocholesterol
- Cholesterol
- Lanosterol
- Zymosterol
- 7-Dehydrodesmosterol
- Desmosterol
- Cholesterol
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|
| From Cholesterol (to steroids) |
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
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| Steroid hormones |
Corticosteroids
(C21 pregnane) |
| Mineralocorticoids |
- Pregnenolone
- Progesterone
- Cortodoxone
- Corticosterone
- Aldosterone
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|
| Glucocorticoids |
- Pregnenolone
- 17-Hydroxypregnenolone
- 17-Hydroxyprogesterone
- Cortisol
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| Sex steroids |
Androgens
(C19 androstane) |
- DHEA
- Androstenedione/5-Androstenediol
- Testosterone
- Dihydrotestosterone
- DHEA sulfate
- Epitestosterone
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Estrogens
(C18 estrane) |
- Estetrol
- Estrone
- Estradiol
- Estriol
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| Nonhuman |
| Phytosterols |
- Stigmasterol
- Brassicasterol
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| Ergosterols |
- Ergosterol
- Ergocalciferol
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mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
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k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
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m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
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noco (d)/cong/tumr, sysi/epon
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proc, drug (A10/H1/H2/H3/H5)
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- biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- amino acids / intermediates
- tetrapyrroles / intermediates
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UpToDate Contents
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English Journal
- Effects of gender on ketamine-induced conditioned placed preference and urine metabonomics.
- Guo R1, Tang Q2, Ye Y1, Lu X2, Chen F1, Dai X1, Yan Y1, Liao L3.
- Regulatory toxicology and pharmacology : RTP.Regul Toxicol Pharmacol.2016 Jun;77:263-74. doi: 10.1016/j.yrtph.2016.03.007. Epub 2016 Mar 17.
- OBJECTIVE: The aim of this study was to examine whether or not there was a gender difference in CPP (conditioned placed preference) induced by ketamine and to further explore the effect of sex on metabolic responses to ketamine inducing in SD rats.METHODS: We measured ketamine-induced conditioned pl
- PMID 26995028
- Effects of Starvation on Lipid Metabolism and Gluconeogenesis in Yak.
- Yu X1, Peng Q1, Luo X2, An T2, Guan J2, Wang Z1.
- Asian-Australasian journal of animal sciences.Asian-Australas J Anim Sci.2016 Mar 4. doi: 10.5713/ajas.15.0868. [Epub ahead of print]
- This research was conducted to investigate the physiological consequences of yak undernourished. Twelve Maiwa yaks (110.3±5.85kg) were randomly divided into two groups (baseline and starvation group). The yaks of baseline group were slaughtered at day 0, while the other group of yaks were kept in s
- PMID 26954191
- Urine metabonomic study for blood-replenishing mechanism of Angelica sinensis in a blood-deficient mouse model.
- Wang T1, Sun HG1, Hua YL1, Li PL1, Wei YM2.
- Chinese journal of natural medicines.Chin J Nat Med.2016 Mar;14(3):210-9. doi: 10.1016/S1875-5364(16)30018-8.
- This study aimed at determining the effects of Angelica sinensis (AS) on urinary metabolites in blood deficiency mice and exploring its replenishing blood mechanism. Gas chromatography-mass spectrometry (GC-MS) was applied to detect metabolites in the urine samples in different collection periods. P
- PMID 27025368
Japanese Journal
- Alcoholic Ketoacidosis Associated with Multiple Complications : Report of 3 Cases
- TANAKA Masami,MIYAZAKI Yasushi,ISHIKAWA Shinsuke,MATSUYAMA Kimihiko
- Internal medicine 43(10), 955-959, 2004-10-01
- … One patient whose ratio of 3-hydroxybutyric acid to acetoacetic acid was 4.0 was associated with diabetic ketoacidosis. …
- NAID 10013733518
- 3 糸状菌ポリケタイド合成酵素の機能解析 : Aspergillus fumigatsuのテトラヒドロキシナフタレン合成酵素系(口頭発表の部)
- 藤井 勲,安岡 良訓,原田 繁春,海老塚 豊,Tsai Huei-Fung,Kwon-Chung K. J.
- 天然有機化合物討論会講演要旨集 (45), 13-18, 2003-09-01
- … The purified Ayglp converted the heptaketide naphthopyrone YWA1 to the pentaketide T4HN with a release of the diketide acetoacetic acid. …
- NAID 110006682262
Related Links
- acetoacetic acid [ah-se″to-ah-se´tik] one of the ketone bodies formed in the body in metabolism of certain substances, particularly in the liver in the combustion of fats. It is present in the body in increased amounts in abnormal ...
- acetoacetic acid ac·e·to·a·ce·tic acid (ās'ĭ-tō-ə-sē'tĭk, ə-sē'tō-) n. A ketone body that is formed in excessive amounts and excreted in the urine of individuals suffering from starvation or diabetes. Also called diacetic acid.
Related Pictures
★リンクテーブル★
[★]
- 英
- acetoacetic acid, acetoacetate
- 同
- 3-オキソ酪酸 3-oxobutyric acid、β-ケト酪酸 β-ketobutyric acid
- 関
- ケトン体
