2,3-Butanediol   中文名称: 2,3-丁二醇

Absorption, Distribution and Excretion
In a controlled experiment 15 (79%) of 19 severely alcoholic men but only 1 of 22 controls had a serum concentration of greater than or equal to 5 umol/l 2,3-butanediol after ingestion of distilled spirits.

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Metabolism / Metabolites
2-Butanol, 3-hydroxy-2-butanone, and 2,3-butanediol were identified as metabolies in the serum of guinea pigs injected ip with methyl ethyl ketone.
... Glucuronides of 2,3-butanediol /were found/ in the urine of rabbits equivalent to about 20% of the dose given.
In a controlled experiment 15 (79%) of 19 severely alcoholic men but only 1 of 22 controls had a serum concentration of greater than or equal to 5 umol/L 2,3-butanediol after ingestion of distilled spirits. Another diol, 1,2-propanediol, was found in a concentration of greater than or equal to 5 umol/L in all patients' specimens after drinking; but it was also present in lower concentrations in the reference specimens of most of the patients. These data are consistent with the experimental evidence that ethanol can be metabolized in rats to produce 2,3-butanediol and with the epidemiological hypothesis that severely alcoholic men metabolize ethanol by a different pathway than do control subjects.
Understanding the capacity of Paenibacillus polymyxa DSM 365 to tolerate increasing concentrations of 2,3-butanediol (2,3-BD) is critical to engineering a 2,3-BD-overproducing strain. Hence, we investigated the response of P. polymyxa to high 2,3-BD concentrations. In fed-batch cultures (6-L bioreactor) 2,3-BD was accumulated to a maximum concentration of 47 g/L despite the presence of residual 13 g/L glucose in the medium. Concomitantly, accumulation of acetoin, the precursor of 2,3-BD increased after maximum 2,3-BD concentration was reached, suggesting that 2,3-BD was reconverted to acetoin after the concentration tolerance threshold of 2,3-BD was exceeded. Cultures of P. polymyxa were then challenged with levo-2,3-BD (20, 40 and 60 g/L) at 0h in a glucose medium, and a concentration dependent growth inhibition response to levo-2,3-BD was observed. The growth of P. polymyxa was completely inhibited by 60 g/L levo-2,3-BD. Furthermore, P. polymyxa was challenged with incremental 2,3-BD concentrations (20, 40 and 60 g/L at 12, 24 and 36 hr, respectively) to mimic 2,3-BD accumulation during fermentation. Interestingly, 2,3-BD was reconverted to acetoin when its concentration reached 60 g/L, possibly to alleviate 2,3-BD toxicity. Collectively, our findings indicate that 2,3-BD-mediated toxicity is a major metabolic impediment to 2,3-BD overproduction, thus, making it an important metabolic engineering target towards rational design of a 2,3-BD-overproducing strain.
The metabolism of diacetyl (2,3-butanedione), acetoin (3-hydroxy-2-butanone), and 2,3-butanediol, which are metabolites of acetaldehyde, was quantitatively investigated using rat liver homogenate, liver perfusion, and in vivo experiments. Diacetyl and acetoin were reduced to 2,3-butanediol in these experiments, but acetoin and 2,3-butanediol were scarcely oxidized to diacetyl, indicating that the reduction reaction to 2,3-butanediol from diacetyl occurs actively in rat liver. The formation of acetoin from diacetyl required either NADH or NADPH as a reductant, while the reduction of acetoin to 2,3-butanediol required NADH. Acetoin and 2,3-butanediol were more readily accumulated than diacetyl in brain tissue.

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Biological Half-Life
...The clearance rate for ... 2,3-butanediol was independent of dose for the two doses used (0.4 and 0.8 g/kg) and ... the half-life ... /was/ 3.45 hr ... .

Toxicity Summary
IDENTIFICATION AND USE: 2,3-Butanediol is nearly colorless, crystalline solid or liquid. 2,3-Butanediol is used as a crosslinking agent for naphthalene-1,5-diisocyanate in the production of specific hard-rubber products. Derivatives of 2,3-butanediol are important as intermediates in the pharmaceutical industry. 2,3-Butanediols have some interest as humectants and in the synthesis of polymers and plasticizers. HUMAN STUDIES: For erythrocytes a solution of 30% 2,3-butanediol showed relatively low toxicity. Hemolysis was only 2% after 5 hr, but increased to 6% after 21 hr and reached 60% after 46 hr. ANIMAL STUDIES: Effects of 2,3-butanediol on the central nervous system (CNS) were investigated by using the analysis of EEG (electroencephalogram) spectral powers recorded at the frontal cortex in rats. It was found that 2,3-butanediol treatment led to increase in EEG spectral powers by oral and intravenous administrations at relatively low doses. From these findings it can be concluded that 2,3-butanediol has a potent CNS depressant effect. 2,3-Butanediol was not embryotoxic when examined in cultured 10-day rat embryo. 2,3-Butanediol has a negative regulatory effect on rats innate immunity response.

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Interactions
Erythrocytes were stored at 4 degrees C in solutions of phosphate-buffered saline containing 2,3-butanediol and 4% (w/w) trehalose, sucrose, sorbitol, or mannitol. The 2,3-butanediol contained 96.7% (w/w) racemic mixture of the levo and dextro isomers and only 3.1% (w/w) of the meso isomer (2,3-butanediol 97% dl). The concentrations of 2,3-butanediol were 30 and 35% (w/w). A solution of 30% 2,3-butanediol showed relatively low toxicity. Hemolysis was only 2% after 5 hr, but increased to 6% after 21 hr and reached 60% after 46 hr. Adding 4% (w/w) of one of the above compounds drastically decreased the toxicity. The two most efficient were the sugars trehalose and sucrose. With 30% 2,3-butanediol and 4% of any of the four compounds, hemolysis was about 0.6% after 2 days of storage. Furthermore, with trehalose or sucrose, hemolysis remained below 3% for 1 month. With sorbitol or mannitol, hemolysis slowly increased to 2% after 7 days and then increased rapidly. Even with 35% 2,3-butanediol, solutions containing trehalose or sucrose showed low toxicity. Hemolysis was also measured after redilution to buffered solution without 2,3-butanediol and without the additive, to mimic perfusion of organs with cryoprotectants and washing. Minima of hemolysis were observed after a few days of storage. The present solutions also have high glass-forming tendencies. They could be of great interest for organ vitrification.
... A 16 hr pretreatment with either 2-butanone (2.1 mL/kg, orally) or 2,3-butanediol (2.12 mL/kg, orally) markedly enhanced the hepatotoxic response to CCl4 (0.1 mL/kg, ip), as measured by serum glutamic pyruvic transaminase activity and hepatic triglyceride content. In vivo, limited formation of 3-hydroxy-2-butanone occurred after this dose of 2,3-butanediol.

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Non-Human Toxicity Values
LD50 Mouse oral 5462 mg/kg
LD50 Mouse oral 9.0 mL/kg

[1]. Mechanism of 2,3-butanediol stereoisomers formation in a newly isolated Serratia sp. T241. Sci Rep. 2016 Jan 12;6:19257.

Butane-2,3-diol is a butanediol in which hydroxylation is at C-2 and C-3. It is a butanediol, a glycol and a secondary alcohol.
2,3-Butanediol has been reported in Bacillus subtilis, Arabidopsis thaliana, and other organisms with data available.
2,3-butanediol is a metabolite found in or produced by Saccharomyces cerevisiae.

C4H10O2

90.1210

90.068

513-85-9

34439-75-3

262

Colorless to light yellow liquid

1.0±0.1 g/cm3

180.7±0.0 °C at 760 mmHg

25 °C(lit.)

85.0±0.0 °C

0.3±0.7 mmHg at 25°C

1.435

-0.99

40.46

2

2

1

6

30.5

0

O([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])O[H]

OWBTYPJTUOEWEK-UHFFFAOYSA-N

InChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3

butane-2,3-diol

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~1109.63 mM)
H2O : ~100 mg/mL (~1109.63 mM)

配方 1 中的溶解度: ≥ 2.5 mg/mL (27.74 mM) (饱和度未知) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将100 μL 25.0 mg/mL澄清DMSO储备液加入到400 μL PEG300中，混匀；然后向上述溶液中加入50 μL Tween-80，混匀；加入450 μL生理盐水定容至1 mL。
*生理盐水的制备：将 0.9 g 氯化钠溶解在 100 mL ddH₂O中，得到澄清溶液。

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配方 2 中的溶解度: 2.5 mg/mL (27.74 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (这些助溶剂从左到右依次添加，逐一添加), 悬浊液; 超声助溶。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL澄清DMSO储备液加入900 μL 20% SBE-β-CD生理盐水溶液中，混匀。
*20% SBE-β-CD 生理盐水溶液的制备（4°C，1 周）：将 2 g SBE-β-CD 溶解于 10 mL 生理盐水中，得到澄清溶液。

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配方 3 中的溶解度: ≥ 2.5 mg/mL (27.74 mM) (饱和度未知) in 10% DMSO + 90% Corn Oil (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL 澄清 DMSO 储备液加入到 900 μL 玉米油中并混合均匀。

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配方 4 中的溶解度: 140 mg/mL (1553.48 mM) in PBS (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液; 超声助溶.

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。