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(Synonyms: DL-2-羟基丁酸,α-Hydroxybutyric acid) 目录号 : GC65518

2-Hydroxybutyric acid (α-hydroxybutyrate) is a chiral compound having two enantiomers, D-2-hydroxybutyric acid and L-2-hydroxybutyric acid. It is produced in mammalian tissues (principally hepatic) that catabolize L-threonine or synthesize glutathione.

2-Hydroxybutyric acid Chemical Structure

Cas No.:600-15-7

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10mM (in 1mL DMSO)
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100mg
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产品描述

2-Hydroxybutyric acid (α-hydroxybutyrate) is a chiral compound having two enantiomers, D-2-hydroxybutyric acid and L-2-hydroxybutyric acid. It is produced in mammalian tissues (principally hepatic) that catabolize L-threonine or synthesize glutathione.

Chemical Properties

Cas No. 600-15-7 SDF Download SDF
别名 DL-2-羟基丁酸,α-Hydroxybutyric acid
分子式 C4H8O3 分子量 104.1
溶解度 DMSO : 100 mg/mL (960.61 mM; Need ultrasonic) 储存条件 Store at -20°C
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1 mM 9.6061 mL 48.0307 mL 96.0615 mL
5 mM 1.9212 mL 9.6061 mL 19.2123 mL
10 mM 0.9606 mL 4.8031 mL 9.6061 mL
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Research Update

Which Role Plays 2-Hydroxybutyric acid on Insulin Resistance?

Metabolites 2021 Dec 3;11(12):835.PMID:34940595DOI:10.3390/metabo11120835.

Type 2 Diabetes Mellitus (T2D) is defined as a chronic condition caused by beta cell loss and/or dysfunction and insulin resistance (IR). The discovering of novel biomarkers capable of identifying T2D and other metabolic disorders associated with IR in a timely and accurate way is critical. In this review, 2-Hydroxybutyric acid (2HB) is presented as that upheaval biomarker with an unexplored potential ahead. Due to the activation of other metabolic pathways during IR, 2HB is synthesized as a coproduct of protein metabolism, being the progression of IR intrinsically related to the increasing of 2HB levels. Hence, the focus of this review will be on the 2HB metabolite and its involvement in glucose homeostasis. A literature review was conducted, which comprised an examination of publications from different databases that had been published over the previous ten years. A total of 19 articles fulfilled the intended set of criteria. The use of 2HB as an early indicator of IR was separated into subjects based on the number of analytes examined simultaneously. In terms of the association between 2HB and IR, it has been established that increasing 2HB levels can predict the development of IR. Thus, 2HB has demonstrated considerable promise as a clinical monitoring molecule, not only as an IR biomarker, but also for disease follow-up throughout IR treatment.

[Efficient cascade biosynthesis of (S)-2-hydroxybutyric acid]

Sheng Wu Gong Cheng Xue Bao 2021 Dec 25;37(12):4231-4242.PMID:34984870DOI:10.13345/j.cjb.210042.

2-Hydroxybutyric acid (2-HBA) is an important intermediate for synthesizing biodegradable materials and various medicines. Chemically synthesized racemized 2-HBA requires deracemization to obtain optically pure enantiomers for industrial application. In this study, we designed a cascade biosynthesis system in Escherichia coli BL21 by coexpressing L-threonine deaminase (TD), NAD-dependent L-lactate dehydrogenase (LDH) and formate dehydrogenase (FDH) for production of optically pure (S)-2-HBA from bulk chemical L-threonine (L-Thr). To coordinate the production rate and the consumption rate of the intermediate 2-oxobutyric acid in the multi-enzyme cascade catalytic reactions, we explored promoter engineering to regulate the expression levels of TD and FDH, and developed a recombinant strain P21285FDH-T7V7827 with a tunable system to achieve a coordinated multi-enzyme expression. The recombinant strain P21285FDH-T7V7827 was able to efficiently produce (S)-2-HBA with the highest titer of 143 g/L and a molar yield of 97% achieved within 16 hours. This titer was approximately 1.83 times than that of the highest yield reported to date, showing great potential for industrial application. Our results indicated that constructing a multi-enzyme-coordinated expression system in a single cell significantly contributed to the biosynthesis of hydroxyl acids.

Development of efficient microbial cell factory for whole-cell bioconversion of L-threonine to 2-Hydroxybutyric acid

Bioresour Technol 2022 Jan;344(Pt B):126090.PMID:34634464DOI:10.1016/j.biortech.2021.126090.

Production of 2-Hydroxybutyric acid (2-HBA) was attempted in recombinant Escherichia coli W3110 Δtdh ΔilvIH (over)expressing a homologous and mutated threonine dehydratase (ilvA*) and a heterologous 2-ketobutyric acid (2-KBA) reductase from Alcaligenes eutrophus H16 (Ae_ldh). To prevent the degradation of 2-KBA, the aceE, poxB and pflB genes were deleted, and for blocking the 2-HBA degradation, the lldD and dld genes were disrupted. In addition, for efficient NADH regeneration/supply, a heterologous formate dehydrogenase from Candida boidinii (Cb_fdh) was overexpressed. Under anaerobic condition, E. coli W3110 Δtdh ΔilvIH ΔaceE ΔpoxB ΔlldD Δdld ΔpflB could produce > 400 mM 2-HBA in 33 h with the yield of ∼ 0.95 mol/mol. Furthermore, by enhancing the expression of a mutant Cb_fdh, the titer could be increased to ∼ 650 mM in 33 h. This study provides an efficient microbial cell factory for the bioconversion of threonine to 2-HBA with a high yield.

Multi-omics analyses reveal relationships among dairy consumption, gut microbiota and cardiometabolic health

EBioMedicine 2021 Apr;66:103284.PMID:33752125DOI:10.1016/j.ebiom.2021.103284.

Background: Little is known about the interplay among dairy intake, gut microbiota and cardiometabolic health in human prospective cohort studies. Methods: The present study included 1780 participants from the Guangzhou Nutrition and Health Study. We examined the prospective association between habitual dairy consumption (total dairy, milk, yogurt) and gut microbial composition using linear regression after adjusting for socio-demographic, lifestyle and dietary factors. The cross-sectional association of dairy-associated microbial features with cardiometabolic risk factors was examined with a linear regression model, adjusting for potential confounders. Serum metabolomic profiles were analyzed by partial correlation analysis. Findings: There was a significant overall difference in gut microbial community structure (β-diversity) comparing the highest with the lowest category for each of total dairy, milk and yogurt (P < 0.05). We observed that dairy-associated microbes and α-diversity indices were inversely associated with blood triglycerides, while positively associated with high-density lipoprotein cholesterol. A follow-up metabolomics analysis revealed the association of targeted serum metabolites with dairy-microbial features and cardiometabolic traits. Specifically, 2-hydroxy-3-methylbutyric acid, 2-Hydroxybutyric acid and L-alanine were inversely associated with dairy-microbial score, while positively associated with triglycerides (FDR-corrected P < 0.1). Interpretation: Dairy consumption is associated with the gut microbial composition and a higher α-diversity, which provides new insights into the understanding of dairy-gut microbiota interactions and their relationship with cardiometabolic health. Funding: This work was supported by the National Natural Science Foundation of China, Zhejiang Ten-thousand Talents Program, Westlake University and the 5010 Program for Clinical Researches of the Sun Yat-sen University.

Vancomycin pretreatment attenuates acetaminophen-induced liver injury through 2-Hydroxybutyric acid

J Pharm Anal 2020 Dec;10(6):560-570.PMID:33425450DOI:10.1016/j.jpha.2019.11.003.

Liver injury caused by acetaminophen (AP) overdose is a leading public health problem. Although AP-induced liver injury is well recognized as the formation of N-acetyl-p-benzoquinone (NAPQI), a toxic metabolite of AP, resulting in cell damage, emerging evidence indicates that AP-induced liver injury is also associated with gut microbiota. However, the gut microbiota-involved mechanism remains largely unknown. In our study, we found that vancomycin (Vac) pretreatment (100 mg/kg, twice a day for 4 days) attenuated AP-induced liver injury, altered the composition of gut microbiota, and changed serum metabolic profile. Moreover, we identified Vac pretreatment elevated cecum and serum 2-Hydroxybutyric acid (2-HB), which ameliorated AP-induced cell damage and liver injury in mice by reducing AP bioavailability and elevating GSH levels. Our current results revealed the novel role of 2-HB in protecting AP-induced liver injury and add new evidence for gut microbiota in affecting AP toxicity.