创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-10-13 04:27:58 UTC
描述
Tetrahydrofuran (THF) is a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity and a smell similar to diethyl ether. At low concentrations it has a faint, fruity aroma. It is one of the most polar ethers. THF is naturally present in coffee aroma, floured chickpeas, and cooked chicken. It is used in the manufacture of polymers as well as agricultural, pharmaceutical, and commodity chemicals. Because of its widespread use (industrially) and its presence in many foods, THF is a contaminant of exposure and can appear in human biofluids. THF oxidizes readily, which can lead to instability and result in cytotoxicity. In chemical synthesis applications, THF is often used for hydroborations used to synthesize primary alcohols. THF is frequently used as a solvent for Grignard reagents because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent (an organometallic chemical reaction involving alkyl- or aryl-magnesium halides). THF is often used in polymer science. For example, it can be used to dissolve rubber prior to determining its molecular mass using gel permeation chromatography. THF tends to form peroxides on storage in air. (PMID: 16999122, 12742700, 14619948). THF can be degraded by certain strains of Rhodococcus bacteria (PMID: 19230656).
同义词
1:1,4-Epoxybutane
2:Butane alpha,delta-oxide
3:Butylene oxide
4:Furanidine
5:Tetramethylene oxide
6:THF
7:Butane a,delta-oxide
8:Butane α,δ-oxide
9:Butane a,δ-oxide
10:1,4-Epoxy-butane
11:Butane a,D-oxide
12:Cyclotetramethylene
13:Cyclotetramethylene oxide
14:Diethylene oxide
15:Hydrofuran
16:Oxacyclopentane
17:Oxolane
18:Polytetrahydrofuran
19:Tetrahydrofuraan
20:Tetrahydrofurane
21:Tetrahydrofuranne
22:Tetraidrofurano
23:Tetrahydrofuran
inchi标识符
InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
印记键
WYURNTSHIVDZCO-UHFFFAOYSA-N
分类学
description: belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.
description:Tetrahydrofurans
kingdom:Organic compounds
super_class:Organoheterocyclic compounds
class:Tetrahydrofurans
sub_class:
molecular_framework:Aliphatic heteromonocyclic compounds
1:Dialkyl ethers
2:Hydrocarbon derivatives
3:Oxacyclic compounds
4:Aliphatic heteromonocyclic compound
5:Dialkyl ether
6:Ether
7:Hydrocarbon derivative
8:Organic oxygen compound
9:Organooxygen compound
10:Oxacycle
11:Tetrahydrofuran
12:cyclic ether
13:oxolanes
14:saturated organic heteromonocyclic parent
本体论
term:Physiological effect
definition:The effect on an organism physiology, resulting from its exposure to a chemical.
parent_id:
level:1
type:parent
term:Health effect
definition:A health condition or observation associated with a stimuli or with a biological activity of a chemical.
parent_id:7693
*level:2
type:parent
term:Health condition
definition:A health effect that consists on short or long-term disease, condition, disorder, syndrome or constant abnormality.
parent_id:7694
**level:3
type:parent
term:Tetrahydrofuran exposure
definition:
parent_id:7695
***level:4
type:child
term:Disposition
definition:A concept that describes the origin of a chemical, its location within an organism, or its route of exposure.
parent_id:
level:1
type:parent
term:Source
definition:Natural or synthetic origin of a chemical.
parent_id:7724
*level:2
type:parent
term:Endogenous
definition:
parent_id:7735
**level:3
type:child
term:Biological location
definition:The physiological origin within an organism, including anatomical compnents, biofluids and excreta.
parent_id:7724
*level:2
type:parent
term:Subcellular
definition:An anatomical organizational level including a component within a biological cell .
parent_id:7725
**level:3
type:parent
term:Cytoplasm
definition:The portion of the cell contained within the plasma membrane but excluding the nucleus.
parent_id:7730
***level:4
type:child
synonym:Cytoplasma
term:Biofluid and excreta
definition:A liquid, semi-solid or solid material originating in the body.
parent_id:7725
**level:3
type:parent
term:Feces
definition:The material discharged from the bowel during defecation. It consists of undigested food, intestinal mucus, epithelial cells, and bacteria.
parent_id:7731
***level:4
type:child
synonym:Fecal
synonym:Stool
synonym:Faecal
synonym:Faeces
term:Blood
definition:A liquid tissue with the primary function of transporting oxygen and carbon dioxide (nci). it supplies the tissues with nutrients, removes waste products, and contains various components of the immune system defending the body against infection.
parent_id:7731
***level:4
type:child
实验性质
1:
kind:water_solubility
value:1000.0 mg/mL
source:
2:
kind:logp
value:0.46
source:HANSCH,C ET AL. (1995)
3:
kind:melting_point
value:-108.3 °C
source:
4:
kind:boiling_point
value:65.00 °C. @ 760.00 mm Hg
source:The Good Scents Company Information System
预测性质
1:
kind:logp
value:0.35
source:ALOGPS
2:
kind:logs
value:-0.01
source:ALOGPS
3:
kind:solubility
value:69.7 g/L
source:ALOGPS
4:
kind:logp
value:0.53
source:ChemAxon
5:
kind:pka_strongest_basic
value:-4.1
source:ChemAxon
6:
kind:iupac
value:oxolane
source:ChemAxon
7:
kind:average_mass
value:72.1057
source:ChemAxon
8:
kind:mono_mass
value:72.057514878
source:ChemAxon
9:
kind:smiles
value:C1CCOC1
source:ChemAxon
10:
kind:formula
value:C4H8O
source:ChemAxon
11:
kind:inchi
value:InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2
source:ChemAxon
12:
kind:inchikey
value:WYURNTSHIVDZCO-UHFFFAOYSA-N
source:ChemAxon
13:
kind:polar_surface_area
value:9.23
source:ChemAxon
14:
kind:refractivity
value:20.55
source:ChemAxon
15:
kind:polarizability
value:8.14
source:ChemAxon
16:
kind:rotatable_bond_count
value:0
source:ChemAxon
17:
kind:acceptor_count
value:1
source:ChemAxon
18:
kind:donor_count
value:0
source:ChemAxon
19:
kind:physiological_charge
value:0
source:ChemAxon
20:
kind:formal_charge
value:0
source:ChemAxon
21:
kind:number_of_rings
value:1
source:ChemAxon
22:
kind:bioavailability
value:Yes
source:ChemAxon
23:
kind:rule_of_five
value:Yes
source:ChemAxon
24:
kind:ghose_filter
value:No
source:ChemAxon
25:
kind:veber_rule
value:Yes
source:ChemAxon
26:
kind:mddr_like_rule
value:No
source:ChemAxon
生物学性质
1:
cellular:(1):Cytoplasm
2:
biospecimen:(1):Blood
biospecimen:(2):Feces
3:
4:
正常浓度
1:
biospecimen:Feces
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
2:
biospecimen:Feces
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Not Specified
subject_condition:Normal
异常浓度
1:
biospecimen:Blood
concentration_value:6.3 (0.3-25.6)
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Both
patient_information:Tetrahydrofuran exposure
疾病参考
1:
name:Tetrahydrofuran exposure
omim_id:
[1]:
reference_text:Ong CN, Chia SE, Phoon WH, Tan KT: Biological monitoring of occupational exposure to tetrahydrofuran. Br J Ind Med. 1991 Sep;48(9):616-21.
pubmed_id:1911404
综合参考
Li, Haixia; Yin, Hengbo; Jiang, Tingshun; Hu, Tongjie; Wu, Jing; Wada, Yuji. Cyclodehydration of 1,4-butanediol to tetrahydrofuran catalyzed by supported silicotungstic acid. Catalysis Communications (2006), 7(10), 778-782.
蛋白质结合
1:
reference_text:Dietzen DJ, Wilhite TR, Kenagy DN, Milliner DS, Smith CH, Landt M: Extraction of glyceric and glycolic acids from urine with tetrahydrofuran: utility in detection of primary hyperoxaluria. Clin Chem. 1997 Aug;43(8 Pt 1):1315-20.
pubmed_id:9267307
2:
reference_text:Sadler BM, Chittick GE, Polk RE, Slain D, Kerkering TM, Studenberg SD, Lou Y, Moore KH, Woolley JL, Stein DS: Metabolic disposition and pharmacokinetics of [14C]-amprenavir, a human immunodeficiency virus type 1 (HIV-1) protease inhibitor, administered as a single oral dose to healthy male subjects. J Clin Pharmacol. 2001 Apr;41(4):386-96.
pubmed_id:11304895
3:
reference_text:Ilett KF, Ethell BT, Maggs JL, Davis TM, Batty KT, Burchell B, Binh TQ, Thu le TA, Hung NC, Pirmohamed M, Park BK, Edwards G: Glucuronidation of dihydroartemisinin in vivo and by human liver microsomes and expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2002 Sep;30(9):1005-12.
pubmed_id:12167566
4:
reference_text:Zhao B, Tham SY, Lu J, Lai MH, Lee LK, Moochhala SM: Simultaneous determination of vitamins C, E and beta-carotene in human plasma by high-performance liquid chromatography with photodiode-array detection. J Pharm Pharm Sci. 2004 Jun 30;7(2):200-4.
pubmed_id:15367376
5:
reference_text:Unni LK, Becker RE: Determination of heptylphysostigmine in plasma by high-performance liquid chromatography with electrochemical detection. J Chromatogr. 1992 Jan 17;573(2):275-81.
pubmed_id:1601960
6:
reference_text:Clayton PT, Leonard JV, Lawson AM, Setchell KD, Andersson S, Egestad B, Sjovall J: Familial giant cell hepatitis associated with synthesis of 3 beta, 7 alpha-dihydroxy-and 3 beta,7 alpha, 12 alpha-trihydroxy-5-cholenoic acids. J Clin Invest. 1987 Apr;79(4):1031-8.
pubmed_id:3470305
7:
reference_text:Breithaupt H, Wilfling M: Determination of mexiletine in biological fluids by high-performance liquid chromatography. J Chromatogr. 1982 Jun 11;230(1):97-105.
pubmed_id:7107772
8:
reference_text:Imbenotte M, Azaroual N, Cartigny B, Vermeersch G, Lhermitte M: Identification and quantitation of xenobiotics by 1H NMR spectroscopy in poisoning cases. Forensic Sci Int. 2003 Apr 23;133(1-2):132-5.
pubmed_id:12742700
9:
reference_text:Mahendra S, Alvarez-Cohen L: Kinetics of 1,4-dioxane biodegradation by monooxygenase-expressing bacteria. Environ Sci Technol. 2006 Sep 1;40(17):5435-42.
pubmed_id:16999122
10:
reference_text:Authors unspecified: International Conference on Harmonisation; final recommendations on the revision of the permitted daily exposures for two solvents, n-methylpyrrolidone and tetrahydrofuran, according to the maintenance procedures for the guidance Q3C Impurities: Residual Solvents; Availability. Notice. Fed Regist. 2003 Nov 13;68(219):64352-3.
pubmed_id:14619948
11:
reference_text:Yao Y, Lv Z, Min H, Lv Z, Jiao H: Isolation, identification and characterization of a novel Rhodococcus sp. strain in biodegradation of tetrahydrofuran and its medium optimization using sequential statistics-based experimental designs. Bioresour Technol. 2009 Jun;100(11):2762-9. doi: 10.1016/j.biortech.2009.01.006. Epub 2009 Feb 18.
pubmed_id:19230656