bis(propan-2-yl) fluorophosphonate

• ChemBase编号: 559
• 分子式: C6H14FO3P
• 平均质量: 184.1457242
• 单一同位素质量: 184.06645916
• SMILES: P(=O)(F)(OC(C)C)OC(C)C
• Canonical SMILES: CC(OP(=O)(OC(C)C)F)C
• InChI: InChI=1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3
• InChIKey: MUCZHBLJLSDCSD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: bis(propan-2-yl) fluorophosphonate
• IUPAC传统名: isoflurophate
• 商标名: Diisopropyl Fluoridophosphate; Diisopropyl Fluorophosphate; Diisopropyl Fluorophosphonate; Diisopropyl Phosphofluoridate; Diisopropyl Phosphorofluoridate; Diisopropylfluorfosfat; Disiopropyl Fluorophosphonate; Dyflos; Floropryl; Fluorodiisopropyl Phosphate; Fluoropryl; Fluostigmine; Fluropryl; Humorsol; Isofluorophate; Isofluorphate; Isoflurophosphate; Isopropyl Fluophosphate; Isopropyl Phosphorofluoridate; Neoglaucit; O,O-Diisopropyl Fluorophosphate; PF-3
• 别名: 二异丙基氟磷酸酯; 氟代磷酸二异丙酯; 氟磷酸二异丙酯; DFP; Diflupyl; Diflurophate; Diisopropoxyphosphoryl Fluoride; Isoflurophate; DIFP; Diisopropylfluorophosphate; Diisopropyl fluorophosphate; Phosphorofluoridic Acid Bis(1-methylethyl) Ester; Phosphorofluoridic Acid Diisopropyl Ester; Dyflos; Floropryl; Fluorodiisopropyl phosphate; Fluostigmine; Isoflurophate; Isopropyl Fluophosphate; Diisopropyl phosphorofluoridate; Phosphoric acid diisopropyl ester fluoride

登记号

• CAS号: 55-91-4
• EC号: 200-247-6
• MDL号: MFCD00008873
• Beilstein号: 1723307
• PubChem SID: 46504499; 160964022; 24893303; 24863641
• PubChem CID: 5936
• CHEBI ID: 17941
• ATC码: S01EB07
• CHEMBL: 1025
• Chemspider ID: 5723
• DrugBank ID: DB00677
• KEGG ID: D00043
• 美国药典/FDA物质标识码: 12UHW9R67N
• 维基百科标题: Diisopropyl_fluorophosphate

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 1.7603906
• LogD (pH = 7.4): 1.7603906
• Log P: 1.7603906
• 摩尔折射率: 40.888 cm^3
• 极化性: 16.348886 Å^3
• 极化表面积: 35.53 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.1
• LOG S: -1.43
• 溶解度: 6.78e+00 g/l

分子性质

理化性质

• 溶解度: 1.54E+004 mg/L; Acetone; anhydrous isopropanol: soluble0.1-0.5 M (stable for months if stored at -70 °C); Benzene; H2O: soluble1.5% at 25 °C (very unstable (at pH 7.5, half-life = 1 hr); decomposed by alkali.)
• 外观: Colourless Liquid
• 熔点: -82 °C(lit.); -82°C (-115.6°F)
• 沸点: 183°C (361.4°F) (1013 mbar); 46°C/5mm; 62 °C/9 mmHg(lit.)
• 密度: 1.06 g/mL at 25 °C(lit.)
• 折射率: n20/D 1.385(lit.)
• 蒸汽压: 0.58 mmHg ( 20 °C)
• 疏水性(logP): 1.4

安全信息

• 保存条件: Refrigerator
• RTECS编号: TE5075000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 3382
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 1
• 危险公开号: 26/27/28
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300 +H310 + H330
• GHS警示性声明: P260-P264-P280-P284-P301 + P310-P302 + P350
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3382 6.1/PG 1
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... PTGS1(5742), PTGS2(5743)

产品相关信息

• 纯度: ≥97.0% (GC)
• 线性分子式: [(CH3)2CHO]2POF

详细说明

DrugBank - DB00677

• Drug Groups: approved
• Description: An irreversible cholinesterase inhibitor with actions similar to those of echothiophate. It is a powerful miotic used mainly in the treatment of glaucoma. Its vapor is highly toxic and it is recommended that only solutions in arachis oil be used therapeutically. (From Martindale, The Extra Pharmacopoeia, 29th ed, p1330)
• Indication: For use in the eye to treat certain types of glaucoma and other eye conditions, such as accommodative esotropia.
• Pharmacology: Isoflurophate is used as ocular drops in the treatment of chronic glaucoma. Isoflurophate is an organophosphorus compound that acts as an irreversible cholinesterase inhibitor. As such, it displays parasympathomimetic effects. Isoflurophate is used in the eye to treat certain types of glaucoma and other eye conditions, such as accommodative esotropia. They may also be used in the diagnosis of certain eye conditions, such as accommodative esotropia. Isoflurophate damages the acetylcholinesterase enzyme and is therefore irreversible, however, pralidoxime can displace organophosphates such as isoflurophate from acetylcholinesterase, but only if administered before isoflurophate damages (alkylates) the enzyme.
• Toxicity: Signs of overdose include increased sweating, loss of bladder control, muscle weakness, nausea, vomiting, diarrhea, or stomach cramps or pain, shortness of breath, tightness in chest, or wheezing, slow or irregular heartbeat, unusual tiredness or weakness, watering of mouth.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Sigma Aldrich - D0879

Analysis Note
使用浓度通常为 0.10mM。苯甲基磺酰氟 (PMSF) 是一种更安全的丝氨酸蛋白酶替代抑制剂。
Other Notes
Stored properly at 2-8°C, in an unopened bottle, DIFP should be stable for a minimum of two years. DIFPis unstable when exposed to moisture. DIFP will develop a dark yellow color upon decomposition.
Biochem/physiol Actions
丝氨酸蛋白酶（如胰蛋白酶和胰凝乳蛋白酶）和乙酰胆碱酯酶的强效抑制剂；还抑制组织蛋白酶 G、胆碱脂酶、凝血因子 Xa、白细胞弹性蛋白酶、胰弹性蛋白酶、组织激肽释放酶、血纤维蛋白熔酶、枯草杆菌蛋白酶以及凝血酶。乙酰胆碱酯酶的抑制作用使该化合物具有特别强的毒性。抑制由篦麻毒素和细菌毒素诱导的细胞凋亡。

Sigma Aldrich - D126004

Analysis Note
使用浓度通常为 0.10mM。苯甲基磺酰氟 (PMSF) 是一种更安全的丝氨酸蛋白酶替代抑制剂。
Application
强效的乙酰胆碱酯酶抑制剂。1,2
Biochem/physiol Actions
丝氨酸蛋白酶（如胰蛋白酶和胰凝乳蛋白酶）和乙酰胆碱酯酶的强效抑制剂；还抑制组织蛋白酶 G、胆碱脂酶、凝血因子 Xa、白细胞弹性蛋白酶、胰弹性蛋白酶、组织激肽释放酶、血纤维蛋白熔酶、枯草杆菌蛋白酶以及凝血酶。乙酰胆碱酯酶的抑制作用使该化合物具有特别强的毒性。抑制由篦麻毒素和细菌毒素诱导的细胞凋亡。

Sigma Aldrich - 38399

Analysis Note
使用浓度通常为 0.10mM。苯甲基磺酰氟 (PMSF) 是一种更安全的丝氨酸蛋白酶替代抑制剂。
Other Notes
Potent inhibitor of chymotrypsin and other enzymes (e.g. serine hydrolases)1; Inhibition of carboxypeptidase but not DAP I2
Biochem/physiol Actions
丝氨酸蛋白酶（如胰蛋白酶和胰凝乳蛋白酶）和乙酰胆碱酯酶的强效抑制剂；还抑制组织蛋白酶 G、胆碱脂酶、凝血因子 Xa、白细胞弹性蛋白酶、胰弹性蛋白酶、组织激肽释放酶、血纤维蛋白熔酶、枯草杆菌蛋白酶以及凝血酶。乙酰胆碱酯酶的抑制作用使该化合物具有特别强的毒性。抑制由篦麻毒素和细菌毒素诱导的细胞凋亡。

Toronto Research Chemicals - D455300

A potent inhibitor of serine proteases such as trypsin and chymotrypsin, and of acetylcholinesterase.

参考文献

• Sarin, A., et al.: J. Exp. Med., 178, 1693 (1993)
• Takahashi, M., et al.: Mol. Reprod. Dev., 38, 310 (1994)