β-ヒドロキシ酪酸
WordNet
- to remain unmolested, undisturbed, or uninterrupted -- used only in infinitive form; "let her be"
- work in a specific place, with a specific subject, or in a specific function; "He is a herpetologist"; "She is our resident philosopher" (同)follow
- have life, be alive; "Our great leader is no more"; "My grandfather lived until the end of war" (同)live
- be identical to; be someone or something; "The president of the company is John Smith"; "This is my house"
- happen, occur, take place; "I lost my wallet; this was during the visit to my parents house"; "There were two hundred people at his funeral"; "There was a lot of noise in the kitchen"
- have the quality of being; (copula, used with an adjective or a predicate noun); "John is rich"; "This is not a good answer"
- occupy a certain position or area; be somewhere; "Where is my umbrella?" "The toolshed is in the back"; "What is behind this behavior?"
- spend or use time; "I may be an hour"
- stake on the outcome of an issue; "I bet $100 on that new horse"; "She played all her money on the dark horse" (同)wager, play
- the act of gambling; "he did it on a bet" (同)wager
- maintain with or as if with a bet; "I bet she will be there!" (同)wager
- second in order of importance; "the candidate, considered a beta male, was perceived to be unable to lead his party to victory"
- the 2nd letter of the Greek alphabet
- preliminary or testing stage of a software or hardware product; "a beta version"; "beta software"
- beets (同)genus Beta
PrepTutorEJDIC
- 《連結語として補語を伴なって…『である』,…だ,…です / 《位置・場所を表す語句を伴って》(…に)『ある』,いる(occupy a place or situation) / 〈物事が〉『存在する』,ある(exist);〈生物が〉生存する,生きている(live) / 行われる,起こる,発生する(take place, occur) / 存続する,そのままでいる(remain as before) / 《『be to』 do》 / …する予定である,…することになっている / …すべきだ / 《受動態の不定詞を伴って》…できる / 《命令》…するのだ / 《条件節に》…する意図がある / 《『if…were to』 do》…するとしたなら / 《『be』 do『ing』》《進行形》 / 《進行中の動作》…している,しつつある / 《近い未来》…しようとしている,するつもり / 《動作の反復》(いつも)…している / 《『be』+『他動詞の過去分詞』》《受動態》…される,されている / 《『be』+『自動詞の過去分詞』》《完了形》…した[状態にある]
- 『かけ』・(…との)かけ《+『with』+『名』》 / かけた物(金) / かけの対象 / 〈金・物〉'を'『かける』 / (かけ事・ゲームなどで)〈人〉‘と'『かけをする』《+『名』〈人〉+『on』+『名』》 / (…に)『かける』《+『on』(『against』)+『名』(one's do『ing』)》
- ベータ(ギリシア語アルファベットの第2文字;B,β;英語のB,b に遭当)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/04/30 12:23:59」(JST)
[Wiki en表示]
beta-Hydroxybutyric acid
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Names |
IUPAC name
3-Hydroxybutanoic acid
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Identifiers |
CAS Registry Number
|
300-85-6 Y |
ChEBI |
CHEBI:20067 Y |
ChEMBL |
ChEMBL1162496 Y |
ChemSpider |
428 Y |
InChI
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InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) Y
Key: WHBMMWSBFZVSSR-UHFFFAOYSA-N Y
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InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
Key: WHBMMWSBFZVSSR-UHFFFAOYAO
|
IUPHAR ligand |
1593 |
Jmol-3D images |
Image
Image |
MeSH |
beta-Hydroxybutyrate |
PubChem |
441 |
SMILES
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O=C(O)CC(O)C
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CC(CC(=O)O)O
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Properties |
Molecular formula
|
C4H8O3 |
Molar mass |
104.10 g·mol−1 |
Appearance |
white solid |
Melting point |
44-46 |
Related compounds |
Other anions
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hydroxybutyrate |
Related carboxylic acids
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propionic acid
lactic acid
3-hydroxypropanoic acid
malonic acid
butyric acid
hydroxypentanoic acid |
Related compounds
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erythrose
threose
1,2-butanediol
1,3-butanediol
2,3-butanediol
1,4-butanediol |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|
Y verify (what is: Y/N?) |
Infobox references |
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beta-Hydroxybutyric acid (also known as beta-hydroxybutyrate, 3-hydroxybutyric acid or 3-hydroxybutyrate) is an organic compound with the formula CH3CH(OH)CH2CO2H. It is a beta hydroxy acid. It is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. Its oxidized and polymeric derivatives occur widely in nature.
Contents
- 1 Biosynthesis
- 2 Laboratory and industrial chemistry
- 3 See also
- 4 References
Biosynthesis
In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA in the fasting state. The biosynthesis is catalyzed by the enzyme beta-hydroxybutyrate dehydrogenase.
Although not a ketone itself, the concentration of beta-hydroxybutyrate, like that of other ketone bodies, is raised in ketosis. The compound can be used as an energy source by the brain when blood glucose is low.[1] Diabetic patients can have their ketone levels tested via urine or blood to indicate diabetic ketoacidosis. In alcoholic ketoacidosis, this ketone body is produced in greatest concentration. Both types of ketoacidosis result in an increase beta-hydroxybutyrate to oxaloacetate ratio, resulting in TCA cycle stalling and shifting of glucose towards ketone body production.[clarification needed]
Laboratory and industrial chemistry
beta-Hydroxybutyric acid is the precursor to polyesters, which are biodegradable plastics. Known as poly(3-hydroxybutyrate), this polymer is also produced biologically by the bacteria Alcaligenes eutrophus.[2]
beta-Hydroxybutyrate can be extracted from poly(3-hydroxybutyrate) by acid hydrolysis.[3]
See also
- Hydroxybutyric acid
- Ketogenesis
References
- ^ O. E. Owen et al. (1967). "Brain Metabolism during Fasting". The Journal of Clinical Investigation 46 (10): 1589–1595. doi:10.1172/JCI105650. PMC 292907. PMID 6061736.
- ^ Yoshiharu Doi, Masao Kunioka, Yoshiyuki Nakamura, Kazuo Soga (1988). "Nuclear magnetic resonance studies on unusual bacterial copolyesters of 3-hydroxybutyrate and 4-hydroxybutyrate". Macromolecules 21 (9): 2722–2727. doi:10.1021/ma00187a012.
- ^ Dieter Seebach, Albert K. Beck, Richard Breitschuh, and Kurt Job "Direct Degradation of the Biopolymer Poly[(R)-3-Hydroxybutrric Acid to (R)-3-Hydroxybutanoic Acid and Its Methyl Ester" Org. Synth. 1993, 71, 39. doi:10.15227/orgsyn.071.0039
UpToDate Contents
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English Journal
- Regulation of the cholesterol efflux transporters ABCA1 and ABCG1 in retina in hemochromatosis and by the endogenous siderophore 2,5-dihydroxybenzoic acid.
- Ananth S1, Gnana-Prakasam JP1, Bhutia YD1, Veeranan-Karmegam R1, Martin PM1, Smith SB2, Ganapathy V3.Author information 1Department of Biochemistry and Molecular Biology, Georgia Regents University, Augusta, GA 30912, USA.2Department of Cellular Biology and Anatomy, Georgia Regents University, Augusta, GA 30912, USA.3Department of Biochemistry and Molecular Biology, Georgia Regents University, Augusta, GA 30912, USA. Electronic address: vganapat@gru.edu.AbstractHypercholesterolemia and polymorphisms in the cholesterol exporter ABCA1 are linked to age-related macular degeneration (AMD). Excessive iron in retina also has a link to AMD pathogenesis. Whether these findings mean a biological/molecular connection between iron and cholesterol is not known. Here we examined the relationship between retinal iron and cholesterol using a mouse model (Hfe(-/-)) of hemochromatosis, a genetic disorder of iron overload. We compared the expression of the cholesterol efflux transporters ABCA1 and ABCG1 and cholesterol content in wild type and Hfe(-/-) mouse retinas. We also investigated the expression of Bdh2, the rate-limiting enzyme in the synthesis of the endogenous siderophore 2,5-dihydroxybenzoic acid (2,5-DHBA) in wild type and Hfe(-/-) mouse retinas, and the influence of this siderophore on ABCA1/ABCG1 expression in retinal pigment epithelium. We found that ABCA1 and ABCG1 were expressed in all retinal cell types, and that their expression was decreased in Hfe(-/-) retina. This was accompanied with an increase in retinal cholesterol content. Bdh2 was also expressed in all retinal cell types, and its expression was decreased in hemochromatosis. In ARPE-19 cells, 2,5-DHBA increased ABCA1/ABCG1 expression and decreased cholesterol content. This was not due to depletion of free iron because 2,5-DHBA (a siderophore) and deferiprone (an iron chelator) had opposite effects on transferrin receptor expression and ferritin levels. We conclude that iron is a regulator of cholesterol homeostasis in retina and that removal of cholesterol from retinal cells is impaired in hemochromatosis. Since excessive cholesterol is pro-inflammatory, hemochromatosis might promote retinal inflammation via cholesterol in AMD.
- Biochimica et biophysica acta.Biochim Biophys Acta.2014 Apr;1842(4):603-12. doi: 10.1016/j.bbadis.2014.01.010. Epub 2014 Jan 23.
- Hypercholesterolemia and polymorphisms in the cholesterol exporter ABCA1 are linked to age-related macular degeneration (AMD). Excessive iron in retina also has a link to AMD pathogenesis. Whether these findings mean a biological/molecular connection between iron and cholesterol is not known. Here w
- PMID 24462739
- Ketone body metabolism and sleep homeostasis in mice.
- Chikahisa S1, Shimizu N1, Shiuchi T1, Séi H2.Author information 1Department of Integrative Physiology, Institute of Health Biosciences, The University of Tokushima Graduate School, 3-18-15 Kuramoto-cho, Tokushima 770-8503, Japan.2Department of Integrative Physiology, Institute of Health Biosciences, The University of Tokushima Graduate School, 3-18-15 Kuramoto-cho, Tokushima 770-8503, Japan. Electronic address: sei@tokushima-u.ac.jp.AbstractA link has been established between energy metabolism and sleep homeostasis. The ketone bodies acetoacetate and β-hydroxybutyrate, generated from the breakdown of fatty acids, are major metabolic fuels for the brain under conditions of low glucose availability. Ketogenesis is modulated by the activity of peroxisome proliferator-activated receptor alpha (PPARα), and treatment with a PPAR activator has been shown to induce a marked increase in plasma acetoacetate and decreased β-hydroxybutyrate in mice, accompanied by increased slow-wave activity during non-rapid eye movement (NREM) sleep. The present study investigated the role of ketone bodies in sleep regulation. Six-hour sleep deprivation increased plasma ketone bodies and their ratio (acetoacetate/β-hydroxybutyrate) in 10-week-old male mice. Moreover, sleep deprivation increased mRNA expression of ketogenic genes such as PPARα and 3-hydroxy-3-methylglutarate-CoA synthase 2 in the brain and decreased ketolytic enzymes such as succinyl-CoA: 3-oxoacid CoA transferase. In addition, central injection of acetoacetate, but not β-hydroxybutyrate, markedly increased slow-wave activity during NREM sleep and suppressed glutamate release. Central metabolism of ketone bodies, especially acetoacetate, appears to play a role in the regulation of sleep homeostasis.
- Neuropharmacology.Neuropharmacology.2014 Apr;79:399-404. doi: 10.1016/j.neuropharm.2013.12.009. Epub 2013 Dec 17.
- A link has been established between energy metabolism and sleep homeostasis. The ketone bodies acetoacetate and β-hydroxybutyrate, generated from the breakdown of fatty acids, are major metabolic fuels for the brain under conditions of low glucose availability. Ketogenesis is modulated by the activ
- PMID 24361452
- L-Cysteine supplementation reduces high-glucose and ketone-induced adhesion of monocytes to endothelial cells by inhibiting ROS.
- Kanikarla-Marie P1, Jain SK.Author information 1Department of Pediatrics, Louisiana State University Health Sciences Center, 1501 Kings Highway, P.O. Box 33932, Shreveport, LA, 71130, USA.AbstractType 1 diabetic (T1D) patients are hyperglycemic and also show elevated blood levels of ketone bodies, particularly acetoacetate (AA) and β-hydroxybutyrate (BHB). T1D patients have a greater risk of developing endothelial dysfunction and cardiovascular disease (CVD). Supplementation with cysteine-rich milk proteins has been shown to be beneficial in improving various biomarkers of endothelial dysfunction and CVD. This study examines whether L-cysteine (LC) per se prevents monocyte adhesion to endothelial cells, a critical step in endothelial dysfunction. Human umbilical vein endothelial cells and THP-1 monocytes were pretreated with and without LC (500 μM) for 2 h and then exposed to ketones (AA or BHB, 0-4 mM) and/or high glucose (HG) (25 mM) for 24 h. This study shows that LC reduces HG and ketone-induced ROS production, ICAM-1 expression, and the adhesion of monocytes to endothelial cells. This study provides a biochemical mechanism by which milk protein supplementation can be beneficial in preventing the excess endothelial dysfunction and CVD seen in diabetic patients.
- Molecular and cellular biochemistry.Mol Cell Biochem.2014 Mar 14. [Epub ahead of print]
- Type 1 diabetic (T1D) patients are hyperglycemic and also show elevated blood levels of ketone bodies, particularly acetoacetate (AA) and β-hydroxybutyrate (BHB). T1D patients have a greater risk of developing endothelial dysfunction and cardiovascular disease (CVD). Supplementation with cysteine-r
- PMID 24627243
Japanese Journal
- Differential protein profiles of Bradyrhizobium japonicum USDA110 bacteroid during soybean nodule development(Soil Biology)
- Nomura Mika,Arunothayanan Hatthaya,Dao Tan Van [他],LE Hoa Thi-Phuong,KANEKO Takakazu,SATO Shusei,TABATA Satoshi,TAJIMA Shigeyuki
- Soil science and plant nutrition 56(4), 579-590, 2010-08
- … In addition, proteins related to the chaperonin and a synthetic enzyme of the poly-beta-hydroxybutyrate were expressed at high abundance. …
- NAID 110008144356
- Metabolic and Physical Predictors of Post-parturient Diseases in Dairy Cattle
- 渡邉 卓彌,安岡 幸,鈴木 隆秀,中田 健,及川 伸
- 獣医疫学雑誌 14(1), 17-18, 2010
- … Blood samples were once collected in 2 to 14 days before expected calving in order to determine serum concentrations of nonesterified fatty acids (NEFA), beta-hydroxybutyrate (BHB) and apolipoprotein B-100 (apoB). …
- NAID 130000438060
- Characterization of human DHRS6, an orphan short chain dehydrogenase/reductase enzyme : a novel, cytosolic type 2 R-beta-hydroxybutyrate dehydrogenase
Related Links
- beta-hydroxybutyrate A ketone body or salt of 3-hydroxybutyric acid involved in fatty acid metabolism, which is increased in diabetic ketoacidosis. Specimen Plasma from grey top tube. Ref range < 0.42 mmol/L. Method
- What Is Beta-Hydroxybutyrate?. Beta-hydroxybutyrate (BHB) is an acidic chemical produced in the body in response to a lowering of its ability to digest glucose for energy. The medical profession uses the measuring of ...
Related Pictures
★リンクテーブル★
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- 英
- β-hydroxybutyrate, β-hydroxybutyric acid, beta-hydroxybutyrate
- 同
- 3-ヒドロキシ酪酸 3-hydroxybutyrate 3-hydroxybutyric acid,D-3-ヒドロキシ酪酸 D-3-hydroxybutyrate,ヒドロキシ酪酸 hydroxybutyrate
- 関
- ケトン体、酪酸
- 3-hydroxybutyrate カルボキシ基の炭素が1位
- β-hydroxybutyrate カルボキシ基に隣接する炭素がα位
- 脂肪のβ酸化が亢進するときに生じる。
- 3分子のアセチルCoAでHMG-CoAを生じ、HMG-CoAリアーゼによりアセト酢酸が生じる
[★]
β、ベータ
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