β-ヒドロキシ酪酸
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）』「2014/05/02 14:12:13」(JST)
[Wiki en表示]
| beta-Hydroxybutyric acid |
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| Identifiers |
| CAS number |
300-85-6 Y |
| PubChem |
441 |
| ChemSpider |
428 Y |
| MeSH |
beta-Hydroxybutyrate |
| ChEBI |
CHEBI:20067 Y |
| ChEMBL |
CHEMBL1162496 Y |
| IUPHAR ligand |
1593 |
| Jmol-3D images |
Image 1
Image 2 |
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O=C(O)CC(O)C
CC(CC(=O)O)O
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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
InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
Key: WHBMMWSBFZVSSR-UHFFFAOYAO
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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 |
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 noted otherwise, data are 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. It, 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. The biosynthesis is catalyzed by the enzyme beta-hydroxybutyrate dehydrogenase.
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
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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
- glycerides
- 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
- Efficient production and secretion of pyruvate from Halomonas sp. KM-1 under aerobic conditions.
- Kawata Y1, Nishimura T2, Matsushita I2, Tsubota J2.
- AMB Express.AMB Express.2016 Dec;6(1):22. doi: 10.1186/s13568-016-0195-y. Epub 2016 Mar 18.
- The alkaliphilic, halophilic bacterium Halomonas sp. KM-1 can utilize both hexose and pentose sugars for the intracellular storage of bioplastic poly-(R)-3-hydroxybutyric acid (PHB) under aerobic conditions. In this study, we investigated the effects of the sodium nitrate concentration on PHB accumu
- PMID 26989057
- Curcumin Induces Apoptosis of Colorectal Cancer Stem Cells by Coupling with CD44 Marker.
- Huang YT1, Lin YW1, Chiu HM2, Chiang BH1.
- Journal of agricultural and food chemistry.J Agric Food Chem.2016 Mar 23;64(11):2247-53. doi: 10.1021/acs.jafc.5b05649. Epub 2016 Mar 7.
- This study investigated the effect of curcumin on colorectal cancer stem cells (CCSCs) and its possible mechanism. Comparison of the metabolic profiles of human adenomatous polyp (N = 61) and colorectal cancer (CRC) (N = 57) tissue found statistically significant differences (p < 0.05) in their c
- PMID 26906122
- Production of Poly (3-Hydroxybutyric Acid) by Ralstonia eutropha in a Biocalorimeter and its Thermokinetic Studies.
- Anusha SM1, Leelaram S1, Surianarayanan M2.
- Applied biochemistry and biotechnology.Appl Biochem Biotechnol.2016 Mar 22. [Epub ahead of print]
- Bioplastic production from microbial sources is an emerging area which provides opportunities even to convert the wastes into bioplastics. Poly (3-hydroxybutyric acid), commonly called as PHB, is a bioplastic, which is stored as intracellular cytoplasmic inclusions in microorganisms. The objectives
- PMID 27003281
Japanese Journal
- Fabrication and characterization of honeycomb-patterned film from poly(ε-caprolactone)/poly((R)-3-hydroxybutyric acid)/reduced graphene oxide composite
- THINH Phung Xuan,BASAVARAJA Chitragara,KIM Kang Il,HUH Do Sung
- Polymer journal 45(10), 1064-1071, 2013-10-15
- NAID 10031200085
- Fabrication and characterization of honeycomb-patterned film from poly(ε-caprolactone)/poly((R)-3-hydroxybutyric acid)/reduced graphene oxide composite
- Thinh Phung Xuan,Basavaraja Chitragara,Kim Kang Il [他]
- Polymer journal 45(10), 1064-1071, 2013-10
- NAID 40019809466
- 1P-220 沖縄で分離した好アルカリ性細菌による廃糖蜜からの(R)-3-ヒドロキシ酪酸生産(一般講演(バイオマス,資源,エネルギー工学),第65回日本生物工学会大会)
Related Links
- Record Information Version 3.5 Creation Date 2005-11-16 08:48:42 -0700 Update Date 2013-05-29 13:25:54 -0600 HMDB ID HMDB00357 Secondary Accession Numbers None Metabolite Identification Common Name 3-Hydroxybutyric ...
- Chemical Entities of Biological Interest (ChEBI) is a freely available dictionary of molecular entities focused on 'small' chemical compounds. ... ChEBI Name (R)-3-hydroxybutyric acid ChEBI ID CHEBI:17066 ChEBI ASCII Name (R)-3 ...
Related Pictures
![Poly[(R)-3-hydroxybutyric acid] natural](https://1mg.info/0/a/0/2747.jpg)
★リンクテーブル★
[★]
- 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
[★]
2-アミノ-3-ヒドロキシ酪酸
[★]
- 関
- hydroxybutyrate