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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/28 08:27:15」(JST)

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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 and a keto 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.

Biosynthesis

In humans, beta-hydroxybutyrate is synthesized in the liver from acetoacetate, the first ketone produced 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. This elevated beta-hydroxybutyrate level seen in ketosis is naturally expected due to the fact that, as mentioned above, it is formed from acetoacetate. The compound can be used as an energy source by the brain when blood glucose is low.^[1] Diabetic patients can have their keto acid 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]

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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1. 成人における糖尿病性ケトアシドーシスおよび高浸透圧性高血糖状態：臨床的特徴、評価、および診断 diabetic ketoacidosis and hyperosmolar hyperglycemic state in adults clinical features evaluation and diagnosis
2. ガンマヒドロキシブチレート（GHB）中毒 gamma hydroxybutyrate ghb intoxication
3. ガンマヒドロキシブチレート（GHB）への依存および離脱 gamma hydroxybutyrate ghb dependence and withdrawal
4. 空腹時ケトアシドーシスおよびアルコール性ケトアシドーシス fasting ketosis and alcoholic ketoacidosis
5. 小児における糖尿病性ケトアシドーシスの臨床的特徴、および診断 clinical features and diagnosis of diabetic ketoacidosis in children

English Journal

Surface grafting of cellulose nanocrystals with poly(3-hydroxybutyrate-co-3-hydroxyvalerate).

Yu HY, Qin ZY.SourceThe Key Laboratory of Advanced Textile Materials and Manufacturing Technology of Ministry of Education, College of Materials and Textile, Zhejiang Sci-Tech University, Hangzhou 310018, China; State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, China; National Engineering Lab of Textile Fiber Materials & Processing Technology, Zhejiang Sci-Tech University. Electronic address: phdyu@zstu.edu.cn.
Carbohydrate polymers.Carbohydr Polym.2014 Jan 30;101:471-8. doi: 10.1016/j.carbpol.2013.09.048. Epub 2013 Sep 23.
Chemically modified cellulose nanocrystals (CNCs) were synthesized by grafting poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV) onto CNCs via homogeneous acylation reaction between N,N-dimethyl formamide (DMF) by using toluene diisocyanate (TDI) as coupling agent and dibutyltin dilaurate as catal
PMID 24299800

The effect of bioartificial constructs that mimic myocardial structure and biomechanical properties on stem cell commitment towards cardiac lineage.

Cristallini C, Cibrario Rocchietti E, Accomasso L, Folino A, Gallina C, Muratori L, Pagliaro P, Rastaldo R, Raimondo S, Saviozzi S, Sprio AE, Gagliardi M, Barbani N, Giachino C.SourceInstitute for Composite and Biomedical Materials, C.N.R., o.u. Pisa, Pisa, Italy. Electronic address: caterina.cristallini@diccism.unipi.it.
Biomaterials.Biomaterials.2014 Jan;35(1):92-104. doi: 10.1016/j.biomaterials.2013.09.058. Epub 2013 Oct 4.
Despite the enormous progress in the treatment of coronary artery diseases, they remain the most common cause of heart failure in the Western countries. New translational therapeutic approaches explore cardiomyogenic differentiation of various types of stem cells in combination with tissue-engineere
PMID 24099712

The increase of apatite layer formation by the poly(3-hydroxybutyrate) surface modification of hydroxyapatite and β-tricalcium phosphate.

Szubert M, Adamska K, Szybowicz M, Jesionowski T, Buchwald T, Voelkel A.SourceFaculty of Chemical Technology, Poznan University of Technology, Poznan, Poland. Electronic address: mm.szubert@gmail.com.
Materials science & engineering. C, Materials for biological applications.Mater Sci Eng C Mater Biol Appl.2014 Jan 1;34:236-44. doi: 10.1016/j.msec.2013.09.023. Epub 2013 Sep 26.
The aim of this study was the surface modification of hydroxyapatite and β-tricalcium phosphate by poly(3-hydroxybutyrate) grafting and characterization of modificates. The bioactivity examination was carried out by the determination to grow an apatite layer on modified materials during incubation
PMID 24268255

Japanese Journal

Enhanced cellular content and lactate fraction of the poly(lactate-co-3-hydroxybutyrate) polyester produced in recombinant Escherichia coli by the deletion of σ factor RpoN

Kadoya Ryosuke,Kodama Yu,Matsumoto Ken'ichiro [他]
Journal of bioscience and bioengineering 119(4), 427-429, 2015-04
NAID 40020435229

Rapid and Direct Compositional Analysis of Poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in Whole Bacterial Cells by Thermally Assisted Hydrolysis and Methylation-Gas Chromatography

BAIDURAH Siti,KUBO Yasuko,KUNO Mitsuhiro [他]
Analytical Sciences 31(2), 79-83, 2015-02
NAID 40020357911

Age-related changes in the diurnal variation of ketogenesis in patients with type 2 diabetes and relevance to hypoglycemic medications

Nakayama Hitomi,Tokubuchi Ichiro,Wada Nobuhiko,Tsuruta Munehisa,Ohki Tsuyoshi,Oshige Tamami,Sasaki Yuko,Iwata Shinpei,Kato Naoka,Ohtsuka Yoshie,Matsuo Yuko,Tajiri Yuji,Yamada Kentaro
Endocrine Journal 62(3), 235-241, 2015
… The plasma levels of 3-hydroxybutyrate (3HB) and free fatty acid (FFA) were increased before breakfast and before dinner. … However, the 3HB levels were significantly decreased with age, which was most obvious before dinner. …
NAID 130005060853

Related Pictures

Image of ethyl 3-hydroxybutyrate Ethyl 3 hydroxybutyrate 99 100g Methyl (R)-3-hydroxybutyrate is a clear Figure 1] Hydroxybutyrates and poly 3 hydroxybutyrate co 3 Image | Ethyl 3-hydroxybutyrate | C6H12O3

★リンクテーブル★

リンク元	「β-ヒドロキシ酪酸」
拡張検索	「3-hydroxybutyrate dehydrogenase」

「β-ヒドロキシ酪酸」

*beta*-Hydroxybutyric acid
Names
	IUPAC name 3-Hydroxybutanoic acid
Identifiers
CAS Number	300-85-6
ChEBI	CHEBI:20067
ChEMBL	ChEMBL1162496
ChemSpider	428
IUPHAR/BPS	1593
Jmol 3D model	Interactive image; Interactive image
MeSH	beta-Hydroxybutyrate
PubChem	441
	InChI InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) Key: WHBMMWSBFZVSSR-UHFFFAOYSA-N ; InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7) Key: WHBMMWSBFZVSSR-UHFFFAOYAO ;
	SMILES O=C(O)CC(O)C ; CC(CC(=O)O)O ;
Properties
Chemical formula	C4H8O3
Molar mass	104.11 g·mol−1
Appearance	white solid
Melting point	44-46
Related compounds
Other anions	hydroxybutyrate
Related carboxylic acids	propionic acid; lactic acid; 3-hydroxypropanoic acid; malonic acid; butyric acid; hydroxypentanoic acid
Related compounds	erythrose; threose; 1,2-butanediol; 1,3-butanediol; 2,3-butanediol; 1,4-butanediol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references