• Malonic and ?-keto esters can be conveniently decarboalkoxylated by heating in wet DMSO: J. Org. Chem., 43, 138 (1978), avoiding the need for separate hydrolysis and decarboxylation steps.
• Tosylates or activated halides can be oxidized with DMSO to aldehydes and ketones (Kornblum oxidation). ɑ-Bromo ketones are oxidized at room temperature to ɑ-keto aldehydes: J. Am .Chem. Soc., 79, 6562 (1957). Benzylic halides, on heating in the presence of NaHCO3, give benzaldehydes: J. Am. Chem. Soc., 114, 6227 (1992). Under similar conditions at 150oC, primary alkyl iodides: J. Chem. Soc., 520 (1964), and alkyl chlorides and bromides in the presence of NaI: Synth. Commun., 16, 1343 (1986), are oxidized to aldehydes. Unactivated bromides have also been oxidized to aldehydes in the presence of Ag salts: Tetrahedron Lett., 917 (1974). For oxidation of benzyl alcohols to benzaldehydes, catalyzed by HBr, see: Synlett, 2041 (2002). DMSO is more often used in combination with a variety of activating agents for selective oxidation of primary and secondary alcohols to carbonyl compounds under very mild conditions. For examples, see: Oxalyl chloride, A18012, or Trifluoroacetic anhydride, A13614 (Swern oxidation), Acetic anhydride, L04295 (Albright-Goldman), N,N'-Dicyclohexylcarbodiimide, A10973 (Pfitzner-Moffatt), Sulfur trioxide-pyridine complex, A12202 (Parikh-Doering), Triphosgene, A14932 and Phenyl phosphorodichloridate, A10479. Reviews: Synthesis, 70 (1971); 165 (1981); 857 (1990).
• DMSO is a very weak acid (pKa= 31) but can be deprotonated by NaH, giving "dimsyl sodium", which is a useful strong base e.g. for the Wittig reaction: J. Org. Chem., 28, 1128 (1963).
• Powerful solvent for many inorganic ions, primarily due to solvation of the cations with consequent enhanced reactivity of the counter anions both in increased nucleophilicity and base strength. In DMSO, the relative nucleophilicities of the halide ions are reversed (F- > I-). The rate of aromatic fluorodenitration in a range of polar aprotic solvents was highest for DMSO: J. Fluorine Chem., 35, 591 (1987); see Potassium fluoride, 14130. For enhanced base strength, see e.g.: cyclization of ω-bromo acids to lactones by K2CO3: Org. Synth. Coll., 6, 698 (1988); exhaustive alkylation of ketones with KOH: Tetrahedron Lett., 31, 859 (1990).
• Aromatic amines can be substituted in the para-position by reaction with DMSO in the presence of conc. HCl with or without CuCl to give 4-aminobenzaldehydes: J. Chem. Soc., Perkin 1, 2235 (1992). The intermediate species is thought to be chloromethyl methyl sulfoxide.
A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during cryopreservation. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation. [PubChem]
Indication
For the symptomatic relief of patients with interstitial cystitis.
Pharmacology
Dimethyl Sulfoxide may have anti-inflammatory, antioxidant and analgesic activities. Dimethyl Sulfoxide also readily penetrates cellular membranes. The membrane-penetrating ability of dimethyl sulfoxide may enhance diffusion of other substances through the skin. For this reason, mixtures of idoxuridine and dimethyl sulfoxide have been used for topical treatment of herpes zoster in the United Kingdom.
Toxicity
The oral LD50 of dimethyl sulfoxide in the dog is greater than 10 gm/kg. It is improbable that this dosage level could be obtained with intravesical instillation of dimethyl sulfoxide in the patient.
Affected Organisms
Humans and other mammals
Biotransformation
Dimethyl sulfoxide is metabolized in man by oxidation to dimethyl sulfone or by reduction in dimethyl sulfide. Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.
Absorption
Readily and rapidly absorbed following administration by all routes and distributed throughout the body.
Elimination
Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 1 gal in glass bottle 1, 6×1, 4 L in poly bottle 100, 500 mL in poly bottle 法律信息 ReagentPlus 注册商标 Sigma-Aldrich Co. LLC
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Application 一种用于聚合酶链式反应 (PCR) 的极性非质子溶剂，并可用作保存细胞、组织和器官的玻璃化抗冻剂。 Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 1 L in poly bottle 500 mL in poly bottle
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 1 L in glass bottle 5.5, 7.5, 50, 100, 250, 500 mL in glass bottle 1, 1.5 mL in poly bottle
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Application 已发现二甲基亚砜 (1-10%) 可加速链复性，据信，它还可赋予核酸热稳定性而避免发生脱嘌呤作用。作为 PCR 助溶剂，DMSO 可有助于提高产率，尤其是在长 PCR 技术中。 Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 1 vial in glass bottle 5 vials in glass bottle
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 1 L in glass bottle 100, 500 mL in glass bottle
Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 1, 4 L in poly bottle 18 L in VerSA-Flow™ Legal Information Arkema Inc. 产品 法律信息 ReagentPlus 注册商标 Sigma-Aldrich Co. LLC
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 Other Notes Polybrene / DMSO-assisted gene transfer1
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 18L、200L Pure-Pac® 不锈钢容器包装； 1L、2L Sure/Seal® 瓶包装 View returnable container options. 2 L in Sure/Seal™ 法律信息 Pure-Pac 注册商标 Sigma-Aldrich Co. LLC
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 1, 2, 4×2, 4×4 L in glass bottle 100 mL in glass bottle
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Application 适用于高效液相色谱法、分光光度法、环境检测 Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 1, 6×1, 2, 4×2, 2.5, 4×4 L in glass bottle 20 L in Nowpak™ 100, 12×100, 500 mL in glass bottle 50 L in comp drum 法律信息 CHROMASOLV 注册商标 Sigma-Aldrich Laborchemikalien GmbH
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 包装 1, 6×1, 2, 2.5, 4, 4×4 L in glass bottle 18 L in VerSA-Flow™ 200 L in poly drum 50 L in Pure-Pac™ 2 50 L in comp drum 100, 500, 6×500 mL in glass bottle 400 L in Pure-Pac™ 1
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 Other Notes Pure-Pac® II 容器需要 Micromatic MacroValve 连接器以分配溶剂 (Z560723)。 包装 1, 6×1, 2 L in Sure/Seal™ 18 L in Pure-Pac™ 1 20 L in Pure-Pac™ 2 View returnable container options. 100, 12×100 mL in Sure/Seal™ 200 L in Pure-Pac™ 1 法律信息 Pure-Pac 注册商标 Sigma-Aldrich Co. LLC
Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 General description Watch a 6-minute presentation that demonstrates the effective use of our High Purity Solvents for GC Headspace Analysis Suitability 针对 GC-HS 进行了测试 Protocols & Applications The Utility of Headspace Grade Solvents for the Analysis of Organic Volatile Impurities
Frequently Asked Questions Live Chat and Frequently Asked Questions are available for this Product. Application 培养基中生长的人和动物细胞系通常采用冷冻保存。冷冻可以避免细胞系因遗传漂变而发生改变，并且可以最大限度降低被污染的风险。液氮与冷冻保护剂（诸如 DMSO）结合使用，是广泛采用的细胞保存方法。如果不使用冷冻保护剂，大多数哺乳动物细胞都会冷冻致死。冰晶将对细胞产生机械性损伤，此外电解液浓度、pH 值变化以及蛋白质变性，都将对细胞产生损害。冷冻保护剂将降低凝固点并保持更低的冷却速率，可最大限度减小这些致命影响。经生物技术性能认证 (BPC) 测试的 DMSO 还符合生物技术和组织工程应用的要求。 Caution 容易过度冷却，并在室温下缓慢融化固化的产品放在室温下可以再次液化，对其本身无影响。 Features and Benefits 产品经过消毒和过滤，包装在带隔垫的螺纹盖棕色瓶中，可立即使用。符合·USP 和·EP 测试要求
刺激性 (Xi)