フルフリルアルコール

Furfuryl Alcohol

HCID 7361CAS 98-00-0

基本情報

標準SMILES
OCc1ccco1
InChIKey
XPFVYQJUAUNWIW-UHFFFAOYSA-N
分子式
C5H6O2
平均分子量
98.1 g/mol
単同位体質量
98.03677943

概要

Furfuryl Alcohol can cause cancer according to The Environmental Protection Agency (EPA).

名称と識別子

優先名称
Furfuryl Alcohol
IUPAC
furan-2-ylmethanol
現地名
フルフリルアルコール
英語名
Furfuryl alcohol
分子式
C5H6O2
分子量
98.1

名称と別名

FURFURYL ALCOHOL98-00-02-Furanmethanol2-Furylmethanolfuran-2-ylmethanol2-Furancarbinol2-Furanylmethanol2-FurylcarbinolFurfural alcoholFurfuralcohol2-Furfuryl alcoholFurfuranol
名称をさらに表示
フルフリルアルコール(2-フリル)メタノールα-フリルカルビノール2-フリルカルビノールフラン-2-メタノール(2-フラニル)メタノール2-フラニルメタノール2-(ヒドロキシメチル)フラン2-ヒドロキシメチルフラン2-フラニルメチルアルコール2-フランメタノールフルフルアルコールフルフリルアルコ-ルフルフリルアルコル2-フリルメタノールFAFURANMETHANOLHPFA2-furanemethanolFEMA 2491
Furyl alcohol2-Hydroxymethylfuran5-HydroxymethylfuranFurylcarbinolalpha-Furylcarbinol2-FurfurylalkoholFurfurylcarbMethanol, (2-furyl)-

データベース識別子

CAS
98-00-0
PubChem CID
7361
DTXSID
DTXSID2025347
ChEMBL
CHEMBL308187
ChEBI
CHEBI:207496
UNII
D582054MUH
EC Number
202-626-1
Nikkaji
J3.578E

物性

構造計算による物性

XLogP
0.3
極性表面積
33.4 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
1
重原子数
7

実験および物理化学的性質

Chemical ClassesFlammable agents - 2nd degree
PolymersOther Classes -> Alcohols and Polyols, Other
CosmeticsCosmetics ingredient -> Other (Specify)
SpringerMaterials PropertiesSchoenflies notation
FragrancesFragrance substance (Furfuryl alcohol) -> IFRA amendment 48
LogP · 3 件

log Kow= 0.28

0.28

0.28

物理化学的性質

融点
-29 °C · -29 °C (lit.)
沸点
170 °C · 170 °C (lit.)
比重(密度)
1.135 g/mL · 1.135 g/mL at 25 °C (lit.)
蒸気密度
3.4 · 3.4 (vs air)
蒸気圧
0.5 mm · 0.5 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.486(lit.)

化学的性質

化学的特性Furfuryl alcohol has a very mild, warm, oily, “burnt” odor and a cooked sugar taste.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P318, P319, P321, P330, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (16.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P318, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: 2-Furanmethanol

Hazard Traits - Carcinogenicity

Regulation (EC) No 1831/2003 (amended)

2-Furanmethanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Furanmethanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Furfuryl Alcohol is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

Status: Active Update: 06-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14780

Other Safety InformationIMAP assessments - 2-Furanmethanol: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 3 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Combustible. Above 75 °C explosive vapour/air mixtures may be formed.

Fire PotentialModerate, when exposed to heat; can react with oxidizing materials.
Health Hazards · 2 件

Inhalation causes headache, nausea, and irritation of nose and throat. Vapor irritates eyes; liquid causes inflammation and corneal opacity. Contact of skin with liquid causes dryness and irritation. Ingestion causes headache, nausea, and irritation of mouth and stomach. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use alcohol-resistant foam, water spray, powder, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest. Refer immediately for medical attention.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth. Refer for medical attention .

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageSeparated from strong oxidants, acids and food and feedstuffs. Well closed. Ventilation along the floor.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

毒性情報

Body Burden · 1 件

Furfuryl alcohol was detected in 2 of 8 samples of mother's milk volatiles with two samples collected at each of four sites, Bayonne, NJ, Jersey City, NJ, Pittsburgh, PA, and Baton Rouge, LA; positive samples were from Jersey City and Baton Rouge(1).

Target OrgansEyes, skin, respiratory system, central nervous system
Ecotoxicity ValuesLC50 Daphnia magna (Water flea) 115 mg/L/24 hr; static /formulated product/
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a log Kow of 0.28(2) and a regression-derived equation(3), indicates that furfuryl alcohol is expected to have very high mobility in soil(SRC). The pKa of furfuryl alcohol is 9.55(4), indicating that this compound will primarily exist in its neutral form in the environment(5). Volatilization of furfuryl alcohol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.609 mm Hg(6), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(7). Furfuryl alcohol may volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). Furfuryl alcohol may be susceptible to biodegradation in terrestrial environments based on the observed degradation of 75-79% in 2 weeks(8) and 97% in 5 days (acclimated for 20 days)(9) in aerobic screening tests with activated sludge inoculum.

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a log Kow of 0.28(2) and a regression-derived equation(3), indicates that furfuryl alcohol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.609 mm Hg(4), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(5). The pKa of furfuryl alcohol is 9.55(6), indicating that this compound will primarily exist in its neutral form in the environment(7). According to a classification scheme(8), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Furfuryl alcohol may be susceptible to biodegradation in aquatic environments based on the observed degradation of 75-79% in 2 weeks(10) and 97% in 5 days (acclimated for 20 days)(11) in aerobic screening tests with activated sludge inoculum.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), furfuryl alcohol, which has a vapor pressure of 0.609 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase furfuryl alcohol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.7 hours(SRC), calculated from its rate constant of 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Furfuryl alcohol absorbs light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(5).

Food Survey Values · 1 件

Furfuryl alcohol was found in canned cream, canned kernel, frozen kernel, and fresh kernel forms of cooked sweet corn at concentrations of 1000, 350, 8, and 5 ppb, respectively(1). Concentrations of 500 and 5,900 ug/kg furfuryl alcohol were detected in microwave-oven produced popcorn volatiles(2). Furfuryl alcohol was detected at 2,000 and 2,300 ppb in rice cake volatiles(3). Furfuryl alcohol was detected in the volatiles of three commercial fermented soybean curd brands collected at local markets in Hong Kong at concentrations of 382.5, 412.7, and 1927.6 ug/kg dry sample(4). Furfuryl alcohol was qualitatively detected in the volatiles of raw beef(5). The volatile flavor components of roasted peanuts contained furfuryl alcohol concentrations ranging from 9.54X10-4 to 4.93X10-3 ug/g(6). Furfuryl alcohol was detected at concentrations of 0.19, 1.21, 1.93, and 8.89 ppb in the volatiles of water-boiled duck meat, duck fatty tissue, Cantonese style roasted duck, and Cantonese style roasted duck gravy, respectively(7). Furfuryl alcohol was detected at a concentration of less than the quantitation limit of 10 ppb in nectarine volatiles(8). It was qualitatively detected in the mixture of volatile components from roasted filberts(9), fried bacon, pork, and smoke flavors(10), heated sukyaki mixture (beef, vegetables, and sugar and soy sauce seasonings) and individual sukyaki ingredients (beef and soy sauce)(11), fried chicken (12), and mountain Beaufort cheese(13). It has been listed as a constituent of the compounds which contribute to the aroma of coffee(14).

Adverse EffectsNeurotoxin - Acute solvent syndrome

法規制情報

FDA RequirementsFurfuryl alcohol is an indirect food additive for use only as a component of adhesives.

安全データ

F
8
OEB
A
OEL
TWA: 10 ppm (40 mg/m3), STEL: 15 ppm (60 mg/m3) [skin]
wgk
1
IDLA
75 ppm
tsca
TSCA listed

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

Furfuryl alcohol is oxidized to furoic acid, which is excreted as the glycine conjugate furoyl glycine ... . Furoyl glycine was the major end product in the urine of rats after feeding furfuryl alcohol.

Furfuryl alcohol is first metabolized by oxidation to the aldehyde (furfural) and then to the corresponding acid (furoic acid), followed by decarboxylation to CO2, excreted as the unchanged acid, conjugated with glycine, or condensed with acetic acid. Furoylglycine was identified as the major urinary metabolite in rats after an oral dose of furfuryl alcohol. Furoic acid and furanacrylic acid were also identified as minor metabolites.

Following oral administration of 0.275, 2.75, and 27.5 mg/kg (14)Cfurfuryl alcohol in rats, at least 86 to 89% was absorbed. ... No furfuryl alcohol was identified in the urine. Furoylglycine was the major urinary metabolite (73 to 80% of dose), and furoic acid (1 to 6%) and furanacrylic acid (3 to 8%) were the minor metabolites.

... The major metabolite was furoylglycine and the minor metabolites were furoic-acid and furanacrylic-acid for both FAL and FOL. The extent and rate of excretion of the metabolites were unaffected by dose.

Furfuryl alcohol has known human metabolites that include 2-Sulfoxymethylfuran.

Absorption, Distribution and Excretion · 4 件

... /Investigators/ suggest that furfuryl alcohol is distributed equally through most or all of the body water ... though it appears to have a slight predilection for the brain.

When [C14] furfuryl alcohol at doses up to 27.5 mg/kg bw ... were administered to rats by gavage in corn oil, 83-89% of the radiolabel was excreted in the urine and 2-4% in the feces, and 7% was exhaled as C14-carbon dioxide within 24 hours. Residual radiolabel was distributed primarily to the liver and kidneys, the amount generally being proportional to the dose.

The urine appeared to be the major route of elimination /in rats/ (up to 90%), followed by feces (2.0-4.0% and exhaled CO2 (7.0%).

The comparative metabolism and disposition of furfural (FAL) and furfuryl alcohol (FOL) /in male Fisher 344 rats/ were investigated following oral administration of approximately 0.001, 0.01, and 0.1 of the LD50, corresponding to approximately 0.127, 1.15, and 12.5 mg/kg for FAL and 0.275, 2.75, and 27.5 mg/kg for FOL. At all doses studied, at least 86-89% of the dose of FAL or FOL was absorbed from the gastrointestinal tract. FAL and FOL were extensively metabolized prior to excretion. The major route of excretion was in urine, where 83-88% of the dose was excreted, whereas 2-4% was excreted in the feces. Approximately 7% of the dose from rats treated with FAL at 12.5 mg/kg was exhaled as 14CO2. At 72 hr following administration, the pattern of tissue distribution of radioactivity was similar for both FAL and FOL. Liver and kidney contained the highest, and brain the lowest concentrations of radioactivity. Generally, the concentrations of radioactivity in tissues were proportional to the dose. Almost all of the urinary radioactivity was tentatively identified. No FAL or FOL was detected in urine.

Cellular LocationsCytoplasm

用途と製造

Uses · 6 件

Used as a solvent and as an intermediate in the manufacturing of resins and wetting agents; [Merck Index # 4305] Used as a solvent for tanning agents, dyes, and resins; also used in sealants, cements, and furan and urea-formaldehyde polymers; [HSDB] The most important use is in making poly(furfuryl alcohol) resins to bind sand-based cores and molds in foundries and to produce plastics, cements, mortars, binders, and adhesives. Resins made from furfuryl alcohol are chemical-resistant and nonburning. [ACGIH]

Molding and Core Making [Category: Foundry]

As a solvent for cellulose ethers & esters, ester gum, dyes, coumarone & natural resins; in mfr of phenolic resins & dark-colored thermosetting resins; liq propellant.

Chemical intermediate for tetrahydrofurfuryl alcohol

Used to tan hides /not commercially wide-spread/.

Solvent; manufacture of wetting agents, resins

U.S. Production · 6 件

2023: 25,000,000 - <40,000,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1974) 2.4X10+10 GRAMS

(1986) >50 million-100 million pounds

(1990) >50 million-100 million pounds

For more U.S. Production (Complete) data for FURFURYL ALCOHOL (7 total), please visit the HSDB record page.

Consumption PatternsCLOSE TO 100% AS A REACTANT IN FURAN RESIN PRODUCTION (1974)
Consumer UsesThickening agent
Industry UsesBinder
IFRA Fragrance Standards · 6 件

Furfuryl alcohol

2-Furancarbinol; 2-Furanmethanol; Furfuralcohol; Furfuryl alcohol; α-Furylcarbinol; 2-Furylcarbinol; 2-Furylmethanol; 2-Hydroxymethylfuran

IFRA_STD_143.pdf

48

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Prohibition: This material should not be used as a fragrance ingredient

応用分野 · 7 件

解説フルフリルアルコール,2-ヒドロキシメチルフラン(2-hydroxymethylfuran)ともいう.ちょうじ油,ばいせんしたコーヒーの油,発酵させたタバコの葉などに存在する.フルフラールを高圧水素添加すると得られる.弱い香りのある無色の液体.沸点170 ℃.d204"1.1285.n20D"1.4868.水およびほとんどの有機溶媒に可溶.酸または空気中の酸素で容易に樹脂化する.フラン樹脂の原料,テトラヒドロフラン誘導体の原料のほか,染料や湿潤剤に使われる.LD50 275 mg/kg(ラット,経口).

用途潤滑剤、浸透剤

用途合成樹脂(フラン樹脂)原料、樹脂変性剤、溶剤、化学原料

天然物の起源Reported found in roasted almonds, cooked apple, apple juice, roasted barley, beans, beef fat, canned beef stew, beer, brandy, white bread, cocoa, cocoa bean, roasted coffee, roasted flberts, honey, heated skim milk, dried mushrooms, roasted onion, yellow passion fruit, roasted peanuts, pineapple, popcorn, potato chips, roasted sesame seeds, cheeses, milk, meats, grape wines, cognac, whiskies, soybean products, coconut, corn oil, shrimps, clams and other sources

使用Furfuryl Alcohol has been obtained by yeast reduction of furfural. Furfuryl Alcohol is used as solvent and in the manufacturing of wetting agents, resins.

一般的な説明A clear colorless liquid. Flash point 167°F. Boiling point 171°F. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion and skin contact and moderately toxic by inhalation.

使用用途フルフリルアルコールの主な用途は、合成樹脂原料、樹脂変性剤、溶剤、化学原料、香料などです。溶剤としてはなど多くの分野で利用されています。化学原料としては、含酸素五員環のビルディングブロックとして合成的に有用な化合物です。 また、低分子量のアルコールとして、エッチング後の残渣除去などで半導体デバイス分野でも用いられています。界面活性剤としては湿潤剤に使用される他、黒色顔料の界面活性剤にも用いられている物質です。 合成樹脂としては、主にフラン樹脂としての利用が中心です。鋳造樹脂として酸硬化性鋳型のフラン樹脂にも使用されています。または赤煙硝酸を酸化剤とする自己着火性のロケット燃料としての用途もあります。

調製方法 · 2 件

製造方法Usually prepared from furfural that is obtained by the processing of corncobs; oil obtained by steam distillation of roasted coffee bean meal consists of 50% furfuryl alcohol; prepared industrially by the catalytic reduction of furfural using nickel and Cu-CrO catalysts.

純化方法Distil it under reduced pressure to remove tarry material, shake with aqueous NaHCO3, dry it with Na2SO4 and fractionally distil it under reduced pressure from Na2CO3. It can be further dried by shaking with Linde 5A molecular sieves. [Beilstein 17/3 V 338.]

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補足説明

定義ChEBI: A member of the class of furans bearing a hydroxymethyl substituent at the 2-position.

関連反応

150 件

関連ノート

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