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the 20th letter of the Roman alphabet (同)t

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tritiumの化学記号

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/12/10 13:55:47」(JST)

Tetrahydrofuran (THF), whose preferred IUPAC name was changed in 2013 to oxolane,^[4] is an organic compound with the formula (CH₂)₄O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers.^[5] Being polar and having a wide liquid range, THF is a versatile solvent.

Production

About 200,000 tonnes of tetrahydrofuran are produced annually.^[6] The most widely used industrial process involves the acid-catalyzed dehydration of 1,4-butanediol. Ashland/ISP is one the biggest producers of this chemical route. The method is similar to the production of diethyl ether from ethanol. The butanediol is derived from condensation of acetylene with formaldehyde followed by hydrogenation.^[5] DuPont developed a process for producing THF by oxidizing n-butane to crude maleic anhydride, followed by catalytic hydrogenation.^[7] A third major industrial route entails hydroformylation of allyl alcohol followed by hydrogenation to the butanediol.

Other methods

THF can also be synthesized by catalytic hydrogenation of furan.^[8]^[9] Certain sugars can be converted to THF^{[citation needed]}, although this method is not widely practiced. Furan is thus derivable from renewable resources.

Applications

Polymerization

In the presence of strong acids, THF converts to a linear polymer called poly(tetramethylene ether) glycol (PTMEG), also known as polytetramethylene oxide (PTMO):

n C₄H₈O → −(CH₂CH₂CH₂CH₂O)_n−

This polymer is primarily used to make elastomeric polyurethane fibers like Spandex.^[10]

As a solvent

The other main application of THF is as an industrial solvent for polyvinyl chloride (PVC) and in varnishes.^[5] It is an aprotic solvent with a dielectric constant of 7.6. It is a moderately polar solvent and can dissolve a wide range of nonpolar and polar chemical compounds.^[11] THF is water-miscible and can form solid clathrate hydrate structures with water at low temperatures.^[12]

In the laboratory, THF is a popular solvent when its water miscibility is not an issue. It is more basic than diethyl ether and forms stronger complexes with Li⁺, Mg²⁺, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.^[13] Although similar to diethyl ether, THF is a stronger base.^[14] Thus, while diethyl ether remains the solvent of choice for some reactions (e.g., Grignard reactions), THF fills that role in many others, where strong coordination is desirable and the precise properties of ethereal solvents such as these (alone and in mixtures and at various temperatures) allows fine-tuning modern chemical reactions.

Purification

Commercial THF contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds. Although THF is traditionally dried by distillation from an aggressive desiccant, molecular sieves are far superior.^[15]

Drying of THF
Drying agent	Duration of drying	Water content
None	0 hours	108 ppm
Sodium/benzophenone	48 hours	43 ppm
3 Å molecular sieves (20% by volume)	72 hours	4 ppm

Potential uses and research

THF has been explored as a miscible co-solvent in aqueous solution to aid in the liquefaction and delignification of plant lignocellulosic biomass for production of renewable platform chemicals and sugars as potential precursors to biofuels.^[16] Aqueous THF augments the hydrolysis of glycans from biomass and dissolves the majority of biomass lignin making it a suitable solvent for biomass pretreatment.

THF is often used in polymer science. For example, it can be used to dissolve polymers prior to determining their molecular mass using gel permeation chromatography. THF dissolves PVC as well, and thus it is the main ingredient in PVC adhesives. It can be used to liquefy old PVC cement and is often used industrially to degrease metal parts.

THF is used as a component in mobile phases for reversed-phase liquid chromatography. It has a greater elution strength than methanol or acetonitrile, but is less commonly used than these solvents.

Other uses

THF is also a starting material for the preparation of tetrahydrothiophene. In the presence of a solid acid catalyst, it reacts with hydrogen sulfide.^[17]

THF is used as a solvent in 3D printing when using PLA plastics. It can be used to clean clogged 3D printer parts, as well as when finishing prints to remove extruder lines and add a shine to the finished product.

2-MethylTHF

2-Methyltetrahydrofuran (2-MeTHF) has been promoted as a more ecologically-friendly alternative to THF.^[18] Whereas 2-MeTHF is more expensive, it may provide for greater overall process economy. 2-MeTHF has solvating properties that are intermediate between diethyl ether and THF, has limited water miscibility, and forms an azeotrope with water on distillation. Its lower melting point makes it useful for lower temperature reactions, and its higher boiling point allows procedures under reflux at higher temperatures (relative to THF).

Precautions

THF is considered a relatively nontoxic solvent, with the median lethal dose (LD₅₀) comparable to that for acetone. Reflecting its remarkable solvent properties, it penetrates the skin, causing rapid dehydration. THF readily dissolves latex and is typically handled with nitrile or neoprene rubber gloves. It is highly flammable.

One danger posed by THF follows from its tendency to form highly explosive peroxides on storage in air.

To minimize this problem, commercial samples of THF are often inhibited with butylated hydroxytoluene (BHT). THF should not be distilled to dryness, because the explosive peroxides concentrate in the residue.

References

^ ^a ^b ^c ^d ^e ^f "NIOSH Pocket Guide to Chemical Hazards #0602". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "Tetrahydrofuran". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
^ "New Environment Inc. - NFPA Chemicals". Newenv.com. Retrieved 2016-07-16.
^ "New IUPAC Organic Nomenclature - Chemical Information BULLETIN" (PDF).
^ ^a ^b ^c Müller, Herbert (2005), "Tetrahydrofuran", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a26_221
^ Karas, Lawrence; Piel, W. J. (2004). "Ethers". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons.
^ Budavari, Susan, ed. (2001), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.), Merck, ISBN 0911910131
^ Morrison, Robert Thornton; Boyd, Robert Neilson (1972). Organic Chemistry (2nd ed.). Allyn and Bacon. p. 569.
^ Starr, Donald; Hixon, R. M. (1943). "Tetrahydrofuran". Organic Syntheses. ; Collective Volume, 2, p. 566
^ Pruckmayr, Gerfried; Dreyfuss, P.; Dreyfuss, M. P. (1996). "Polyethers, Tetrahydrofuran and Oxetane Polymers". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons.
^ "Chemical Reactivity". Michigan State University. Retrieved 2010-02-15.
^ "NMR–MRI study of clathrate hydrate mechanisms" (PDF). Fileave.com. Retrieved 2010-02-15.
^ Elschenbroich, C.; Salzer, A. (1992). Organometallics: A Concise Introduction (2nd ed.). Weinheim: Wiley-VCH. ISBN 3-527-28165-7.
^ Lucht, B. L.; Collum, D. B. (1999). "Lithium Hexamethyldisilazide: A View of Lithium Ion Solvation through a Glass-Bottom Boat". Accounts of Chemical Research. 32: 1035–1042. doi:10.1021/ar960300e.
^ Williams, D. B. G.; Lawton, M. (2010). "Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants". Journal of Organic Chemistry. 75: 8351. doi:10.1021/jo101589h. PMID 20945830.
^ Cai, Charles; Zhang, Taiying; Kumar, Rajeev; Wyman, Charles (13 August 2013). "THF co-solvent enhances hydrocarbon fuel precursor yields from lignocellulosic biomass". Green Chemistry. 15: 3140–3145. doi:10.1039/C3GC41214H.
^ Swanston, Jonathan (2005), "Thiophene", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a26_793.pub2
^ "Greener Solvent Alternatives – Brochure" (PDF). Sigmaaldrich.com. Retrieved 2010-02-15.

General reference

Loudon, G. Mark (2002). Organic Chemistry (4th ed.). New York: Oxford University Press. p. 318. ISBN 9780981519432.

External links

International Chemical Safety Card 0578
NIOSH Pocket Guide to Chemical Hazards
U.S. OSHA info on THF
"2-Methyltetrahydrofuran, An alternative to Tetrahydrofuran and Dichloromethane". Sigma-Aldrich. Retrieved 2007-05-23.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. ビタミンB12および葉酸欠乏症の生理学 physiology of vitamin b12 and folate deficiency
2. トリメトプリムスルファメトキサゾール：概要 trimethoprim sulfamethoxazole an overview
3. Uncommon congenital adrenal hyperplasias
4. 内因性および外因性ステロイドの尿中排泄の測定 measurement of urinary excretion of endogenous and exogenous glucocorticoids
5. X連鎖リンパ増殖性疾患 x linked lymphoproliferative disease

English Journal

Sonochemical effect on size reduction of CaCO3 nanoparticles derived from waste eggshells.

Hassan TA, Rangari VK, Rana RK, Jeelani S.SourceDepartment of Materials Science and Engineering, Tuskegee University, Tuskegee, AL 36088, USA. Electronic address: hassant@mytu.tuskegee.edu.
Ultrasonics sonochemistry.Ultrason Sonochem.2013 Sep;20(5):1308-15. doi: 10.1016/j.ultsonch.2013.01.016. Epub 2013 Feb 17.
A novel combination of mechanochemical and sonochemical techniques was developed to produce high-surface-area, bio-based calcium carbonate (CaCO3) nanoparticles from eggshells. Size reduction of eggshell achieved via mechanochemical and followed by sonochemical method. First, eggshells were cleaned
PMID 23473569

High diastereoselective vinylogous Mannich reaction induced by O-pivaloylated d-galactosylamine as the chiral auxiliary: stereoselective synthesis of 8-arylazocan-2-one.

Cui B, Hou G, Cai Y, Miao Z.SourceState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
Carbohydrate research.Carbohydr Res.2013 Jun 7;374:1-7. doi: 10.1016/j.carres.2013.03.020. Epub 2013 Mar 30.
The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-amino aldehyde derivatives has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using a O-pivaloylated galactosyl amine as a chiral template and AlCl3 as a promoter in THF
PMID 23603240

Photoinduced electron transfer of platinum(ii) bipyridine diacetylides linked by triphenylamine- and naphthaleneimide-derivatives and their application to photoelectric conversion systems.

Suzuki S, Matsumoto Y, Tsubamoto M, Sugimura R, Kozaki M, Kimoto K, Iwamura M, Nozaki K, Senju N, Uragami C, Hashimoto H, Muramatsu Y, Konno A, Okada K.SourceGraduate School of Science, Osaka City University, Sugimoto Sumiyoshi-ku, Osaka 558-8585, Japan. suzuki-s@sci.osaka-cu.ac.jp hassy@sci.osaka-cu.ac.jp okadak@sci.osaka-cu.ac.jp.
Physical chemistry chemical physics : PCCP.Phys Chem Chem Phys.2013 Jun 7;15(21):8088-94. doi: 10.1039/c3cp50182e. Epub 2013 Mar 26.
The recently reported efficient charge-separated system based on bipyridine-diacetylide platinum(ii) complexes was applied to photoelectric conversion systems herein, based on the design and synthesis of two triads: MTA-Pt-NDISAc (3, MTA: dimethoxytriphenylamine, Pt: platinum(ii) complex, NDISAc: th
PMID 23532104

Japanese Journal

Photochemical grafting of methyl groups on a Si(111) surface using a Grignard reagent.

Herrera Marvin Ustaris,Ichii Takashi,Murase Kuniaki,Sugimura Hiroyuki
Journal of colloid and interface science 411, 145-151, 2013-12-01
… The preparation involved illuminating a hydrogen-terminated Si(111) that was immersed in a CH3MgBr-THF solution. …
NAID 120005343916

Pd[II]触媒を用いる分子内不斉転写反応の立体化学と合成的応用

上西潤一,河井伸之
有機合成化学協会誌 71(9), 912-925, 2013-09
NAID 40019801754

28aPS-90 ラマン分光法によるTHFクラスレートハイドレートにおける格子振動モードの温度依存性の研究(領域12ポスターセッション,領域12(ソフトマター物理,化学物理,生物物理))

松本悟,藤井康裕,高須雄一,西尾泉
日本物理学会講演概要集 68(2-2), 327, 2013-08-26
NAID 110009755355

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★リンクテーブル★

リンク元	「葉酸」「ビタミンB12」「テトラヒドロ葉酸」
拡張検索	「MTHFR」「5,10-メチレン-THF」「THF類似体」「5dTHF」「MTHFR deficiency」
関連記事	「TH」「T」

「葉酸」

Tetrahydrofuran
Names
	Preferred IUPAC name Oxolane
	Systematic IUPAC name 1,4-Epoxybutane; Oxacyclopentane
	Other names Tetrahydrofuran; Butylene oxide; Cyclotetramethylene oxide; Diethylene oxide; Tetra-methylene oxide
Identifiers
CAS Number	109-99-9 ;
3D model (JSmol)	Interactive image;
Abbreviations	THF
ChEBI	CHEBI:26911 ;
ChemSpider	7737 ;
ECHA InfoCard	100.003.389
PubChem CID	8028;
RTECS number	LU5950000
	InChI InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2 Key: WYURNTSHIVDZCO-UHFFFAOYSA-N ; InChI=1/C4H8O/c1-2-4-5-3-1/h1-4H2 Key: WYURNTSHIVDZCO-UHFFFAOYAI ;
	SMILES C1CCOC1 ;
Properties
Chemical formula	C4H8O
Molar mass	72.11 g·mol−1
Appearance	colorless liquid
Odor	ether-like
Density	0.8892 g/cm3 at 20 °C, liquid
Melting point	−108.4 °C (−163.1 °F; 164.8 K)
Boiling point	66 °C (151 °F; 339 K)
Solubility in water	Miscible
Vapor pressure	132 mmHg (20 °C)
Viscosity	0.48 cP at 25 °C
Structure
Molecular shape	envelope
Dipole moment	1.63 D (gas)
Hazards
Safety data sheet	See: data page
EU classification (DSD) (outdated)	Flammable (F); Irritant (Xi)
R-phrases (outdated)	R11, R19, R20/21/22, R36/37
S-phrases (outdated)	S16, S29, S33
NFPA 704	3 2 1
Flash point	−14 °C (7 °F; 259 K)
Explosive limits	2%–11.8%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1650 mg/kg (rat, oral); 2300 mg/kg (mouse, oral); 2300 mg/kg (guinea pig, oral)
LC50 (median concentration)	21000 ppm (rat, 3 hr)
	US health exposure limits (NIOSH):
PEL (Permissible)	TWA 200 ppm (590 mg/m3)
REL (Recommended)	TWA 200 ppm (590 mg/m3) ST 250 ppm (735 mg/m3)
IDLH (Immediate danger)	2000 ppm
Related compounds
Related heterocycles	Furan; Pyrrolidine; Dioxane
Related compounds	Diethyl ether
Supplementary data page
Structure and; properties	Refractive index (n),; Dielectric constant (εr), etc.
Thermodynamic; data	Phase behaviour; solid–liquid–gas
Spectral data	UV, IR, NMR, MS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: folic acid folate FA
同: プテロイルグルタミン酸 pteroylglutamic acid PteGlu, PGA、フォラシン folacin
ラ: acidum folicum
商: Ｍ.Ｖ.Ｉ.-12、M.V.I.-3、アミノレバンEN配合、エルネオパ1号輸液、エレンタールP、エレンタール配合、エンシュア・リキッド、オーツカＭＶ、ダイメジン・マルチ、ツインラインNF配合、ツインライン配合、ネオパレン1号輸液、ネオラミン・マルチＶ、パンビタン末、ビタジェクト、フェニルアラニン除去ミルク配合、フォリアミン(単剤)、フルカリック１号輸液、ヘパンED配合、マルタミン、ラコールNF配合、ラコール配合、ロイシン・イソロイシン・バリン除去ミルク配合
関: テトラヒドロ葉酸(THF)。プテリン、パラアミノ安息香酸

図：GOO.1459(構造)

概念

PteGluとして摂取された後、速やかに還元(ジヒドロ葉酸還元酵素)されてH4PteGlu(=THF,テトラヒドロ葉酸)となる。
C₁キャリアー

様々な酸化状態のC₁基を転移する

吸収

食品中では9個以下のグルタミン酸が結合したプテロイルグルタミン酸(PteGlu)の形となっている。
小腸絨毛膜のプテロイルポリグルタミン酸加水分解酵素により1個のグルタミン酸のみが結合した形で吸収される。
小腸細胞内で還元され、メチルテトラヒドロ葉酸の形で門脈血に入る
十二指腸、空腸。×回腸

機能

C₁単位の調達

セリン→グリシン (FB.421)
グリシン開裂系 (FB.421)
ヒスチジン代謝 (FB.423)

THF=H4PteGlu

ヒスチジン→…→N-ホルムイミノグルタミン酸+THF→グルタミン酸+5-ホルムイミノ-THF

C₁単位の転移

ホモシステイン→メチオニン (FB.424)
チミジンの生合成 (FB.479)

5,10-CH2H4PteGlu

臨床検査

全血もしくは血清で定量する。
HPLC法により測定する
単位：ng/ml x 2.266 = nmol/L

基準範囲

年齢	平均(範囲)ng/mL
年齢	血清		全血
新生児	24.5	(3-59)	315	(100-960)
3-4月	12.2	(5-30)	99	(20-318)
6-8月	7.7	(3.5-16)	77	(32-176)
1歳	9.3	(3-35)	86	(31-400)
成人	13.1	(7-20)	195	(24-400)

臨床関連

葉酸欠乏症

妊婦の葉酸欠乏→胎児の神経管欠損
大球性貧血

「ビタミンB12」

　　[★]

英: vitamin B12
同: コバラミン cobalamin
商: アリチア配合
関: シアノコバラミン、悪性貧血、ビタミン、メチルコバラミン

構造：FB.387

吸収

食物(コバラミン＋蛋白質)→胃(コバラミン)＋壁細胞が分泌する糖タンパク;内因子→コバラミン-内因子複合体→回腸 (SP.742)

回腸上皮細胞の刷子縁膜にコバラミン-内因子複合体に特異的なレセプターが存在 (SP.742)

細胞内ではβグロブリン(トランスコバラミン II)と結合して血中に入り組織に運ばれる (SPC.280, SPC.742)

部位：　ビタミンB₁₂は回腸。　葉酸は空腸。　鉄も空腸、ついでに十二指腸でも。

機能

コバラミン依存の酵素は全部で十数種ある。コバラミン依存の酵素は分子内転移、メチル転移を触媒 (FB.387)
正常ミエリンの維持 (SPC.280)
葉酸の代謝(葉酸は核酸代謝に関わっている) (SPC.280)
奇数脂肪酸の酸化 (FB.386)

メチルマロニルCoAムターゼの補酵素(奇数脂肪酸の酸化)

補酵素

methylmalonyl-CoA mutase：
methionine synthase：homocysteine + methyl THF－→methionine + THF

必要量

一日の消費量(排泄)：1-3ug (体の貯蔵量の-0.1%) (HIM.643)
体に貯蔵されてる量：2-3mg　→　摂取しなくとも3-4年は欠乏しない

基準値

260-1,050pg/ml(192-775pmol/ml)

判定

低値

巨赤芽球貧血

悪性貧血(内因子抗体、壁細胞抗体？)
胃切除後
萎縮性胃炎

吸収不良をきたす病態：クローン病、セリアック病、吸収不良症候群

高値

血液疾患：顆粒球増加を示す疾患　　　←　　顆粒球由来のビタミンB12輸送蛋白(トランスコバラミン?)が増加するため(QB.G-257)、崩壊した白血球から放出するため(YN.G-53)

慢性骨髄性白血病、真性多血症

臨床関連

白血球の破壊により末梢へのビタミンB12の漏出

亜急性連合性脊髄変性症 SCDC

http://www.shc.usp.ac.jp/shibata/5-16-4.pdf

「テトラヒドロ葉酸」

　　[★]

英: tetrahydrofolate THF, tetrahydrofolic acid THFA H4FA
関: メチルTHF、活性C1単位、葉酸、プテリジン

補因子として働き、C₁単位を転移する
セリン→グリシン (セリンヒドロキシメチルトランスフェラーゼ)
グリシン開裂反応
ヒスチジン分解
ホモシステインからのメチオニン合成
チミンヌクレオチドの合成

dUMP→dTMP

IMPの合成

IMPの合成(IMPからはAMP, GMPができる)

「MTHFR」

　　[★]

メチレンテトラヒドロ葉酸還元酵素

関: methylenetetrahydrofolate reductase

「5,10-メチレン-THF」

　　[★] 5,10-メチレンテトラヒドロ葉酸

同: 5,10-メチレンテトラヒドロ葉酸

「THF類似体」

　　[★]

英: [[]]
同: tetrahydrofolate analog
関: [[]]

同: tetrahydrofolate analog

「5dTHF」

　　[★]

同: 5-deazatetrahydrofolate

同: 5-deazatetrahydrofolate

「MTHFR deficiency」

　　[★]

同: methylenetetrahydrofolate reductase

「TH」

　　[★]

「T」

　　[★]

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f "NIOSH Pocket Guide to Chemical Hazards #0602". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-2] "Tetrahydrofuran". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).

[3] "New Environment Inc. - NFPA Chemicals". Newenv.com. Retrieved 2016-07-16.

[4] "New IUPAC Organic Nomenclature - Chemical Information BULLETIN" (PDF).

[Ullmann-5] Müller, Herbert (2005), "Tetrahydrofuran", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a26_221

[kirk1-6] Karas, Lawrence; Piel, W. J. (2004). "Ethers". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons.

[merck-7] Budavari, Susan, ed. (2001), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.), Merck, ISBN 0911910131

[m_and_b-8] Morrison, Robert Thornton; Boyd, Robert Neilson (1972). Organic Chemistry (2nd ed.). Allyn and Bacon. p. 569.

[9] Starr, Donald; Hixon, R. M. (1943). "Tetrahydrofuran". Organic Syntheses. ; Collective Volume, 2, p. 566

[kirk-10] Pruckmayr, Gerfried; Dreyfuss, P.; Dreyfuss, M. P. (1996). "Polyethers, Tetrahydrofuran and Oxetane Polymers". Kirk‑Othmer Encyclopedia of Chemical Technology. John Wiley & Sons.

[11] "Chemical Reactivity". Michigan State University. Retrieved 2010-02-15.

[12] "NMR–MRI study of clathrate hydrate mechanisms" (PDF). Fileave.com. Retrieved 2010-02-15.

[13] Elschenbroich, C.; Salzer, A. (1992). Organometallics: A Concise Introduction (2nd ed.). Weinheim: Wiley-VCH. ISBN 3-527-28165-7.

[14] Lucht, B. L.; Collum, D. B. (1999). "Lithium Hexamethyldisilazide: A View of Lithium Ion Solvation through a Glass-Bottom Boat". Accounts of Chemical Research. 32: 1035–1042. doi:10.1021/ar960300e.

[15] Williams, D. B. G.; Lawton, M. (2010). "Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants". Journal of Organic Chemistry. 75: 8351. doi:10.1021/jo101589h. PMID 20945830.

[pubs.rsc.org-16] Cai, Charles; Zhang, Taiying; Kumar, Rajeev; Wyman, Charles (13 August 2013). "THF co-solvent enhances hydrocarbon fuel precursor yields from lignocellulosic biomass". Green Chemistry. 15: 3140–3145. doi:10.1039/C3GC41214H.

[17] Swanston, Jonathan (2005), "Thiophene", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a26_793.pub2

[18] "Greener Solvent Alternatives – Brochure" (PDF). Sigmaaldrich.com. Retrieved 2010-02-15.

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THF

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Production

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Polymerization

As a solvent

Purification

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Other uses

2-MethylTHF

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「葉酸」

概念

吸収

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C1単位の調達

C1単位の転移

臨床検査

基準範囲

臨床関連

「ビタミンB12」

吸収

機能

補酵素

必要量

基準値

判定

低値

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臨床関連

「テトラヒドロ葉酸」

「MTHFR」

「5,10-メチレン-THF」

「THF類似体」

「5dTHF」

「MTHFR deficiency」

「TH」

「T」

C₁単位の調達

C₁単位の転移