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아세트산알릴

Allyl acetate

HCID 11584
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
591-87-7
표준 SMILES
C=CCOC(C)=O
InChIKey
FWZUNOYOVVKUNF-UHFFFAOYSA-N
분자식
C5H8O2
평균 분자량
100.12 g/mol
단동위원소 질량
100.05242949

개요

Allyl acetate appears as a liquid. Insoluble in water and slightly less dense than water. Hence floats on water. Poisonous by ingestion and moderately toxic by inhalation and skin contact. Irritating to skin and eyes.

이름 및 식별자

우선 이름
Allyl acetate
IUPAC
prop-2-enyl acetate
현지명
아세트산알릴
영어명
Allyl acetate
분자식
C5H8O2
분자량
100.12

이름 및 동의어

Allyl acetate591-87-73-AcetoxypropeneAcetic acid, 2-propenyl ester3-Acetoxy-1-propeneACETIC ACID, ALLYL ESTER2-Propenyl methanoateDTXSID9024437E4U5E5990INSC-7612DTXCID904437RefChem:554845
이름 더 보기
아세트산,알릴에스터아세트산알릴알릴아세트산알릴아세트산(ALLYLACETATE)아세트산, 알릴 에스터3-아세틸프로펜2-Propenyl acetateACETIC ACID ALLYL ESTERacetated’allyleAllylAcetate99%PROPENYL ACETATEAllyl acetate 99%Allyl Acetate >
209-734-8prop-2-enyl acetate2-Propenyl ethanoateprop-2-en-1-yl acetateNSC 7612MFCD00008721Allyl acetate, 99%Acetic acid, 2-propen-1-yl ester

데이터베이스 식별자

CAS
591-87-7
PubChem CID
11584
DTXSID
DTXSID9024437
ChEMBL
CHEMBL1890774
UNII
E4U5E5990I
EC Number
209-734-8
Nikkaji
J35.906H

물성

구조 계산 물성

XLogP
1
극성 표면적
26.3 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
3
무거운 원자 수
7
형식 전하
0
복잡도
76.1

실험 및 물리화학적 성질

Chemical Classes · 2건

Other Classes -> Esters, Other

Flammable agents - 3rd degree

SpringerMaterials PropertiesDensity
LogP · 2건

log Kow = 0.97

0.97

OdorACRID AT HIGH LEVELS
TasteSOUR, CARAMELLIC, WITH SWEET AFTERTASTE, ACRID AT HIGH LEVELS
Density · 2건

0.9275 g/cu cm at 20 °C

0.928 @ 20°C

Viscosity0.52 cP at 20 °C
Color/FormCOLORLESS LIQUID
Solubility · 2건

Soluble in acetone; miscible in ethanol and ethyl ether.

2.8% in water at 20 °C

Flash Point · 2건

72 °F (NFPA, 2010)

22 °C

Boiling Point · 2건

103.5 °C

103 °C @760 [mm Hg]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P320, P321, P330, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

유해성 정보

Regulatory Information · 3건

Chemical: Acetic acid, 2-propenyl ester

Acetic acid, 2-propenyl ester: HSNO Approval: HSR001241 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Aliphatic allyl esters: Human health tier II assessment
DOT LabelFlammable Liquid Poison
Fire Hazards · 2건

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Fire Potential · 2건

...EVOLVE FLAMMABLE...VAPORS.

Dangerous fire hazard.

Health Hazards · 2건

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

화학 및 산업

약리 정보

Metabolism/Metabolites · 2건

A MERCAPTURIC ACID WAS ISOLATED FROM URINE OF RATS TREATED SC WITH ALLYL ACETATE & IDENTIFIED AS 3-HYDROXYPROPYLMERCAPTURIC ACID N-ACETYL-S-3-HYDROXYPROPYL-L-CYSTEINE.

MERCAPTURIC ACIDS WERE DETECTED IN URINE OF RATS FOLLOWING ADMIN OF VARIOUS ALLYL ESTERS WHICH COULD BE METAB BY ACYL-OXYGEN FISSION OR ALKYL-OXYGEN FISSION TO YIELD 3-HYDROXYMERCAPTURIC ACID OR ALLYLMERCAPTURIC ACID. LATTER OCCURRED ONLY WHEN THE ESTER WAS FORMED FROM A STRONG ACID.

Absorption, Distribution and ExcretionIT IS...ABSORBED THROUGH INTACT SKIN.

용도 및 제조

Uses · 3건

Used to make allyl alcohol and as a synthetic flavoring agent; [HSDB]

SYNTHETIC FLAVOR USEFUL IN CHEESE, BUTTER, FRUIT

Allyl acetate is produced mostly for manufacturing allyl alcohol.

Methods of Manufacturing · 2건

BY DECARBOXYLATION BY HEATING ALLYLMALONIC ACID; OR FROM THE CORRESPONDING ETHYL ESTER PREPARED BY BOILING ETHYL 4-CHLORO-N-VALERATE IN QUINOLINE.

By acetoxylation of propylene.

Household ProductsInformation on 1 consumer products that contain Acetic acid, allyl ester in the following categories is provided:
General Manufacturing Information · 4건

Acetic acid, 2-propen-1-yl ester: ACTIVE

IT IS USED IN NON-ALCOHOLIC BEVERAGES AT 1.0 PPM; ICE CREAM, ICES AT 2.0 PPM; CANDY AT 5.0 PPM; BAKED GOODS AT 5.0 PPM; MARGARINE AT 2.0 PPM.

FEMA NUMBER 2843

ACYLOXY, SUBSTITUTED OR UNSUBSTITUTED ALKENYL ARE EFFECTIVE COCKROACH REPELLENTS.

응용 분야

용도Ally acetate is used in nonalcoholic beverages at 1 ppm, ice cream and ices at 2 ppm, candy at 5 ppm, baked goods at 5 ppm, and margarine at 2 ppm.

관련 반응

60건
반응 기록 만들기
HRID 20616 반응식
HRID 20616반응물로uspto-grants-2010_06
HRID 37329 반응식
HRID 37329반응물로uspto-grants-1995_05
HRID 71244 반응식
HRID 71244반응물로uspto-grants-2014_09
HRID 143687 반응식
HRID 143687반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 155769 반응식
HRID 155769반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 162597 반응식
HRID 162597반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 182872 반응식
HRID 182872반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 304114 반응식
HRID 304114반응물로Training data from https://doi.org/10.1039/C8SC04228D (8/10)
1 / 8 페이지

화합물 노트

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Decomposition
When heated to decomposition it emits acrid smoke and irritating fumes.

물리화학적 성질

녹는점
6 °C · 6°C
끓는 점
103 · 103-104 °C (lit.)
밀도
0.928 g/mL · 0.928 g/mL at 25 °C (lit.)
증기압
27.2 hPa · 27.2 hPa (20 °C)
굴절률
20 · n20/D 1.404(lit.)
인화점
44 °F · 44 °F
저장 조건
2 · 2-8°C
용해도
28 g/L · 28g/L
물리적 상태
액체
색상
무색의
Specific Gravity
0.928 · 0.928
폭발한계
2.1 · 2.1-13.0%(V)
수용성
약간 용해됨
비열
1.84 J/ · Cp(liquid): 1.84 J/(g·K), at 25℃
Merck
14 · 14,285
BRN
1742050 · 1742050
Henry's Law Constant
7.6 · 7.6×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C5H8O2/c1-3-4-7-5(2)6/h3H,1,4H2,2H3
InChIKey
FWZUNOYOVVKUNF-UHFFFAOYSA-N
SMILES
CC(=O)OCC=C
LogP
0.97 · 0.970
NIST
2 · Acetic acid, 2-propenyl ester(591-87-7)
EPA
2 · Acetic acid, 2-propen-1-yl ester (591-87-7)

화학적 성질

Allyl acetate is a flammable, colorless liquid with an acrid odor.

Hazards Summary · 1건

A tumorigen and moderate eye irritant; Causes gastritis, hepatitis, and weight loss in feeding studies of rats; [RTECS] A strong irritant; Irritation and lacrimation observed in animal studies; Enzymatic hydrolysis required for hepatotoxic activation in rat feeding studies; Emergency medical treatment: lacrimators; [HSDB] May irritate or burn skin and eyes; [CAMEO] Effects in gavage study with rats at 100 mg/kg include decreases in hematocrit, increases in ALT and other liver enzymes, necrosis and hemorrhage of the forestomach, and changes in bone marrow, lymph nodes, and thymus; [NTP]

DOT ID and Guide2333 131
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special ReportsCometto-Muniz JE, Cain Ws; Pharmacol Biochem Behav 39 (4): 983-990. Nasal pungency, odor, and eye irritation thresholds for homologous acetates.
Reactivity AlertsHighly Flammable
Reactivity Profile · 1건

ALLYL ACETATE is an ester. Reacts with acids to liberate heat along with alcohols and acids. Generates heat with strong oxidizing acids. The reaction may be sufficiently exothermic to ignite the reaction products. Also generates heat with basic solutions. Generates flammable hydrogen with alkali metals and hydrides. Emits acrid smoke and irritating fumes when heated to decomposition.

안전 및 보호

Fire FightingExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
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 · 2건

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Storage Conditions · 1건

STORAGE TANKS OUTSIDE BUILDING SHOULD BE BUNDED /SRP: DIKED/ TO PREVENT SPREAD OF ACCIDENTALLY ESCAPING LIQUID, & A RAMPED SILL SHOULD BE CONSTRUCTED AT DOORWAYS OF STOREROOMS TO RETAIN FLAMMABLE LIQUID THAT MAY ESCAPE FROM STORAGE VESSELS INSIDE. /ALLYL ALCOHOL/

Nonfire Spill ResponseExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 5건

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

...VAPOR SHOULD BE PREVENTED FROM ESCAPING...INTO WORKROOM BY...EXHAUST VENTILATION. WHEN PROCESSES CANNOT BE ENCLOSED, EXHAUST...HOODS SHOULD BE FITTED TO TRAP & EXTRACT ESCAPING VAPOR BEFORE IT CAN DIFFUSE INTO WORKROOM ATMOSPHERE. /ALLYL ALCOHOL/

PRECAUTIONS MUST BE ADOPTED...TO EXCLUDE OPEN LIGHTS OR ANY AGENCIES CAPABLE OF IGNITING VAPOR WHEN LIQUID IS BEING HANDLED IN A WARM WORKROOM. /ALLYL ALCOHOL/

TO PREVENT THE LIQUID OR VAPOR FROM COMING INTO CONTACT WITH THE WORKERS, PROCESSES IN WHICH ALLYL ALCOHOL IS PRESENT SHOULD...BE CONDUCTED IN ENCLOSED PLANT. /ALLYL ALCOHOL/

For more Preventive Measures (Complete) data for ACETIC ACID, ALLYL ESTER (6 total), please visit the HSDB record page.

Isolation and Evacuation · 2건

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Immediate precautionary measure

Protective Action Criteria (PAC) · 3건

0.42 [ppm]

4.6 [ppm]

28 [ppm]

Personal Protective Equipment (PPE) · 2건

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

WORKERS WHO...HANDLE ALLYL ALCOHOL, OR WHO MAY BE LIABLE TO...EXPOSURE...SHOULD WEAR...PROTECTIVE EQUIPMENT APPROPRIATE TO EXTENT OF... EXPOSURE. ...EYE PROTECTION SHOULD BE PROVIDED /WHEN NECESSARY/. /ALLYL ALCOHOL/

Emergency Response Planning GuidelinesCAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.

독성 정보

Body Burden · 1건

Allyl acetate was identified in approx 40% of the expired air samples collected from an urban population of 28 normal, healthy, non-smoking human subjects(1). It was detected in 36.9% of 387 expired air samples collected from 54 normal, healthy, non-smoking human subjects at a geometric mean concentration of 0.296 ng/l(2).

Interactions · 3건

125 MG/KG TRIORTHOTOLYL PHOSPHATE PRETREATMENT SIGNIFICANTLY INHIBITED RISE IN PLASMA ALANINE-ALPHA-KETOGLUTARATE TRANSAMINASE ACTIVITY & PREVENTED CHANGES IN LIVER MORPHOLOGY PRODUCED BY 60-150 MG/KG ALLYL ACETATE ADMIN ORALLY TO RATS 18 HR AFTER PRETREATMENT.

O.5 TO 10 MG/KG PRETREATMENT WITH THE DEFOLIANT, S,S,S-TRIBUTYLPHOSPHOROTRITHIOATE (DEF) PROTECTED AGAINST HEPATOTOXICITY OF 60 MG/KG ALLYL ACETATE ADMIN ORALLY TO RATS 18 HR LATER.

PRETREATMENT OF RATS WITH 375 MG/KG PYRAZOLE, AN INHIBITOR OF ALCOHOL DEHYDROGENASE, COMPLETELY PREVENTED THE ELEVATION OF PLASMA ALANINE-ALPHA-KETOGLUTARATE TRANSAMINASE (AKT) ACTIVITY AFTER 90 MG/KG ALLYL ACETATE ADMIN.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 80(SRC), determined from a log Kow of 0.97(2) and a regression-derived equation(3), indicates that allyl acetate is expected to have high mobility in soil(SRC). Volatilization of allyl acetate from moist soil surfaces may be important(SRC) given an estimated Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 27.2 mm Hg(4), and water solubility, 2.8X10+4 mg/l(5). The potential for volatilization of allyl acetate from dry soil surfaces may exist(SRC) based on this compound's vapor pressure(4). In general, acetates are expected to be readily biodegradable(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 80(SRC), determined from a log Kow of 0.97(2) and a regression-derived equation(3), indicates that allyl acetate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based on an estimated Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 27.2 mm Hg(4), and water solubility, 2.8X10+4 mg/l(5). Estimated volatilization half-lives for a model river and model lake are 9.8 hours and 6.0 days, respectively(3). According to a classification scheme(5), an estimated BCF of 3.2(3,SRC), from a log Kow(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Estimated hydrolysis half-lives of 1.1 years and 41 days at pH values of 7 and 8, respectively(7), indicate hydrolysis is expected to be a slow process(SRC). In general, acetates are expected to be readily biodegradable(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), allyl acetate, which has a vapor pressure of 27.2 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase allyl acetate 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 14 hours(SRC) from the estimated rate constant(3).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ongoing Test Status · 1건

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=591-87-7]

Soil Adsorption/Mobility · 1건

The Koc of allyl acetate is estimated as approximately 80(SRC), using a log Kow of 0.97(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that allyl acetate is expected to have high mobility in soil.

Atmospheric ConcentrationsSOURCE DOMINATED: Allyl acetate was identified in ambient air samples collected near the Kin-Buc chemical waste disposal site in Edison, NJ in 1976 at an estimated concentration of 31 ug/cu m(1).
Human Toxicity Excerpts · 2건

VAPOR & LIQ...IRRITATING TO SKIN & MUCOUS MEMBRANE. PRODUCES LACRIMATION & CORNEAL BURNS. LIQ MAY PRODUCE FIRST OR SECOND DEGREE BURNS WITH BLISTERING & SUPERFICIAL NECROSIS. ... INHALED VAPOR MAY LEAD TO PULMONARY EDEMA... /ALLYL ALCOHOL/

ALLYL ACETATE...IS HIGHLY IRRITANT & TOXIC BY INHALATION, INGESTION, EYE, & DERMAL CONTACT.

Artificial Pollution SourcesAllyl acetate's use in the production of allyl alcohol(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1건

An estimated BCF of 3.2 was calculated for allyl acetate(SRC), using a log Kow of 0.97(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1건

The Henry's Law constant for allyl acetate is estimated as 1.3X10-4 atm-cu m/mole at 20 °C(SRC) from its vapor pressure, 27.2 mm Hg(1), and water solubility, 2.8X10+4 mg/l(2). This Henry's Law constant indicates that allyl acetate is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is approximately 9.8 hours(SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is approximately 6.0 days(SRC). Allyl acetate's Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of allyl acetate from dry soil surfaces may exist(SRC) based on a vapor pressure of 27.2 mm Hg(1).

Non-Human Toxicity Excerpts · 3건

IT HAS BEEN OBSERVED THAT UNSATURATED ALIPHATIC ESTERS /WHICH INCLUDE THE ALLYL ESTER OF ACETIC ACID/ EXHIBIT IRRITANT AND LACRIMATORY PROPERTIES...

ALLYL ACETATE CAUSES SLIGHT SKIN IRRITATION AND MODERATE EYE EFFECT IN RABBITS. /FROM TABLE/

ENZYMATIC HYDROLYSIS IS A NECESSARY STEP IN ACTIVATION OF ALLYL ACETATE TO HEPATOTOXINS FROM ORAL ADMIN OF 60-150 MG/KG TO RATS.

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
AF1750000
ridadr
UN 2333
독성
LD50: 0.13 g/kg orally in rats; 1.1 ml/kg dermally in rabbits (Smyth); LD50 in rats, mice (mg/kg): 142, 170 orally (Jenner)
HS 번호
29153990
risk_code
11-21-23/25-36-25
hazard_code
F,T
safety_code
16-26-36-45-27
포장분류
II
위험 등급
3
기존화학 물질
KE-00850
자연 발화 온도
705 °F
Hazard Classifications
Acute Tox. 2 InhalationAcute Tox. 3 OralAcute Tox. 4 DermalEye Irrit. 2Flam. Liq. 2
스토리지 클래스
3 - Flammable liquids
유해 물질 데이터
591-87-7(Hazardous Substances Data)

일반 설명A liquid. Insoluble in water and slightly less dense than water. Hence floats on water. Flash point below 75°F. Poisonous by ingestion and moderately toxic by inhalation and skin contact. Irritating to skin and eyes.

제조 방법 · 1건

생산 방법Allyl acetate is produced by the following methods: decarboxylation of allylmalonic acid with heat, boiling ethyl 4- chloro-N-valerate in quinoline, and acetoxylation of propylene. Allyl acetate is produced primarily for manufacturing allyl alcohol. It is also used as a synthetic flavoring for cheese, butter, and fruit.

상·하류 제품 정보

상류 원료

아세트산 팔라듐 (II)아세트산 칼륨

하류 제품

알릴 알코올프탈산디알릴모노머바이사이클로[2.2.2]옥탄Triisopropyl phosphate1,1,3-TrimethoxypropaneAllyl benzoate트리에틸인산염1-노나데센알릴아닐린Diethyl allylphosphonate3-(4-TERT-부틸페닐)-1-프로펜3-Methylisoquinoline알릴말론산디에틸에스테르옥시란메탄올아세테이트