퍼퓨릴 알코올

Furfuryl Alcohol

HCID 7361CAS 98-00-0

기본 정보

표준 SMILES
OCc1ccco1
InChIKey
XPFVYQJUAUNWIW-UHFFFAOYSA-N
분자식
C5H6O2
평균 분자량
98.1 g/mol
단동위원소 질량
98.03677943

개요

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

이름 및 식별자

우선 이름
Furfuryl Alcohol
IUPAC
furan-2-ylmethanol
현지명
퍼퓨릴 알코올
영어명
Furfuryl alcohol
분자식
C5H6O2
분자량
98.1

이름 및 동의어

FURFURYL ALCOHOL98-00-02-Furanmethanol2-Furylmethanolfuran-2-ylmethanol2-Furancarbinol2-Furanylmethanol2-FurylcarbinolFurfural alcoholFurfuralcohol2-Furfuryl alcoholFurfuranol
이름 더 보기
퍼퓨릴알코올푸르푸릴알코올푸르푸릴알콜2-푸릴메탄올2-하이드록시메틸푸란2-푸란카르비놀2-푸란메탄올2-푸란메탄올푸르푸릴알콜퍼퓨릴 알코올2-(하이드록시메틸)푸란2-푸라닐메탄올2-푸란카비놀2-푸르푸릴 알코올2-푸릴카비놀알파-푸란카비놀알파-푸르푸릴 알코올알파-푸릴카비놀알파-하이드록시메틸푸란푸르푸랄 알코올FAFURANMETHANOLHPFA2-furanemethanolFEMA 2491
Furyl alcohol2-Hydroxymethylfuran5-HydroxymethylfuranFurylcarbinolalpha-Furylcarbinol2-FurfurylalkoholFurfurylcarbMethanol, (2-furyl)-

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
0.3
극성 표면적
33.4 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
1
무거운 원자 수
7

실험 및 물리화학적 성질

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 · 3건

log Kow= 0.28

0.28

0.28

물리화학적 성질

녹는점
-29 °C · -29 °C (lit.)
끓는 점
170 °C · 170 °C (lit.)
밀도
1.135 g/mL · 1.135 g/mL at 25 °C (lit.)
증기 밀도
3.4 · 3.4 (vs air)
증기압
0.5 mm · 0.5 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.486(lit.)

화학적 성질

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

안전 및 규제

GHS 분류

GHS Classification · 6건

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)

유해성 정보

Regulatory Information · 6건

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 · 3건

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 · 2건

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.

안전 및 보호

Fire Fighting · 2건

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

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

First Aid Measures · 4건

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 · 2건

· 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 · 3건

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).

독성 정보

Body Burden · 1건

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 · 3건

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 · 1건

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

규제 정보

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

안전 데이터

OEB
A
OEL
TWA: 10 ppm (40 mg/m3), STEL: 15 ppm (60 mg/m3) [skin]
wgk
1
IDLA
75 ppm
tsca
TSCA listed
rtecs
LU9100000

화학 및 산업

약리 정보

Metabolism/Metabolites · 5건

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 · 4건

... /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

용도 및 제조

Uses · 6건

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 · 6건

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 · 6건

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

응용 분야 · 3건

출처Reported 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

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

일반 설명A 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.

제조 방법 · 1건

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.

공급사50 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]

추가 설명

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

관련 반응

150건

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