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숙신산 디메틸

Dimethyl Succinate

HCID 7820
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
106-65-0
표준 SMILES
COC(=O)CCC(=O)OC
InChIKey
MUXOBHXGJLMRAB-UHFFFAOYSA-N
분자식
C6H10O4
평균 분자량
146.14 g/mol
단동위원소 질량
146.0579088

개요

Dimethyl succinate is a colorless liquid. (USCG, 1999)

이름 및 식별자

우선 이름
Dimethyl Succinate
IUPAC
dimethyl butanedioate
현지명
숙신산 디메틸
영어명
Dimethyl succinate
분자식
C6H10O4
분자량
146.14

이름 및 동의어

DIMETHYL SUCCINATE106-65-0Dimethyl butanedioateDimethylsuccinateButanedioic acid, dimethyl esterSuccinic acid, dimethyl esterMethyl butanedioateFEMA No. 2396DTXSID50251521,4-dimethyl butanedioateButanedioic acid, 1,4-dimethyl esterNSC-52209
이름 더 보기
숙신산다이메틸숙신산디메틸숙신산다이메틸다이메틸석시네이트숙신산 다이메틸다이메틸 뷰테인다이오에이트메틸 석시네이트뷰테인이산, 1,4-다이메틸 에스터뷰테인이산, 다이메틸 에스터석시네이트, 다이메틸석신산 다이메틸석신산, 다이메틸 에스터FEMA 2396Succinic acid dimethylDimethyl 2,3-butanedioateDBE-4 DIBASIC ESTER, 99% (DIMETHYL SUCCI NATE)DBE-4ESTASOL(R)
914I2127JRDTXCID005152RefChem:134276203-419-9Methyl succinateSuccinic acid dimethyl esterDBE-4 dibasic esterMFCD00008466

데이터베이스 식별자

CAS
106-65-0
PubChem CID
7820
DTXSID
DTXSID5025152
ChEMBL
CHEMBL556489
ChEBI
CHEBI:165393
UNII
914I2127JR
EC Number
203-419-9
Nikkaji
J3.244A

물성

구조 계산 물성

XLogP
0.4
극성 표면적
52.6 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
5
무거운 원자 수
10
형식 전하
0
복잡도
114

실험 및 물리화학적 성질

SolventsSolvents -> Esters (<C12)
Cosmetics · 2건

Cosmetic ingredients (Dimethyl Succinate) -> CIR (Cosmetic Ingredient Review)

Emollient

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Dimethyl succinate) -> IFRA transparency List
LogP · 3건

Log Kow = 0.35

0.35

0.19

OdorPLEASANT, ETHEREAL, WINEY ODOR
TasteFRUITY, WINEY, & BURNING FLAVOR
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 5건

1.117 (USCG, 1999) - Denser than water; will sink

1.1202 @ 18 °C/4 °C

1.114-1.118

1.117

1.1202 @ 18°C

Flavoring AgentsEU Flavoring substances
Color/FormCOLORLESS LIQ @ ROOM TEMP; SOLIDIFIES WHEN COLD

안전 및 규제

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

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 61.8% (730 of 1181) of all reports.

Warning

H319 (36.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 1181 reports by companies from 9 notifications to the ECHA C&L Inventory.

Warning

유해성 정보

Regulatory Information · 4건

Chemical: Butanedioic acid, dimethyl ester

Butanedioic acid, 1,4-dimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanedioic acid, 1,4-dimethyl ester 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)

Status: Active Update: 25-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15043

Dimethyl succinate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Butanedioic acid, dimethyl ester: Environment tier I assessment
DOT LabelCombustible Liquid
Fire HazardsThis chemical is combustible. Vapor forms explosive mixtures with air. (NTP, 1992)
Health HazardsMay be harmful by inhalation, ingestion or skin absorption. May cause irritation. (USCG, 1999)
Hazards SummaryMay cause irritation; [MSDSonline]
FDA Requirements · 1건

화학 및 산업

약리 정보

Mechanism of Action · 2건

Dibasic esters are a solvent mixture of dimethyl adipate; dimethyl glutarate, and dimethyl succinate used in the paint and coating industry. Subchronic inhalation toxicity studies have demonstrated that dibasic ester induce a mild degeneration of the olfactory, but not the respiratory, epithelium of the rat nasal cavity. Carboxylesterase-mediated hydrolysis of the individual dibasic esters is more efficient in olfactory than in respiratory mucosal homogenates. In the present study, an in vitro system of cultured rat nasal explants was utilized to determine if dibasic ester toxicity is dependent on a metabolic activation by nonspecific carboxylesterase. Explants from both the olfactory and the respiratory regions of the female rat nasal cavity were incubated for 2 hr in Williams' medium E containing 10-100 mM dimethyl adipate, dimethyl glutarate, or dimethyl succinate, dibasic ester caused a dose-related increase in nasal explant acid phosphatase release, a biochemical index of cytotoxicity. HPLC analysis demonstrated parallel increases in the carboxylesterase-mediated formation of monomethyl ester metabolites. Diacid metabolite production in the nasal explant system was not entirely concentration-dependent. Metabolite concentrations and acid phosphatase release were generally greater in olfactory than respiratory tissues. dibasic ester-induced cytotoxicity and acid metabolite production were markedly attenuated in nasal tissue excised from rats which were pretreated with bis(p-nitrophenyl)phosphate, a carboxylesterase inhibitor. This study presents a viable in vitro method for assessing organic ester cytotoxicity in the rat nasal cavity. It was shown that dibasic ester are weak nasal toxicants under the conditions of this system. It was further demonstrated that dibasic ester toxicity is dependent on a carboxylesterase-mediated activation. A similar mechanism was proposed for the nasal toxicity induced by other organic esters following inhalation exposure.

Inhalation exposure of rats to dibasic esters revealed lesions of the nasal olfactory epithelium similar to those observed with other ester solvents. Female rats are more sensitive to these effects than are male rats. It has been proposed that carboxylesterase conversion of inhaled esters within nasal tissues to organic acids may be a critical biochemical step in converting these chemicals to toxic substances. These experiments measured the kinetic parameters Vmax, Km, Ksi, and V/K for the hydrolysis of the dibasic esters in the target nasal tissue, olfactory mucosa, and nontarget tissue, respiratory mucosa. It was determined that under the conditions of these experiments, diacid metabolites are not formed. Esterase activity was inhibited by pretreatment with bis p-nitrophenyl phosphate. Vmax values for the three dibasic esters were 5- to 13-fold greater in olfactory mucosa than respiratory mucosa for male or female rats. V/K values were 4- to 11-fold greater in olfactory mucosa than respiratory mucosa for male or female rats. V/K was similar between male and female olfactory mucosa when dimethyl glutarate was used as the substrate. With dimethyl succinate or dimethyl adipate as the substrate, V/K for female olfactory tissue was 0.5- or 2-fold that of males, respectively. Differences in V/K were mainly due to decreases in KM associated with increasing carbon chain length. Substrate inhibition was observed at dibasic ester concentrations greater than approximately 25 mM, which are unlikely to be achieved in vivo. These results lend further support to the hypothesis that organic acid accumulation in the target tissue, olfactory mucosa, plays a significant role in the pathogenesis of dibasic ester-induced nasal lesions. The mechanism nay be applicable to a wide range of inhaled esters.

관련 반응

59건
반응 기록 만들기
HRID 1493 반응식
HRID 1493반응물로uspto-grants-1998_03
HRID 1561 반응식
HRID 1561반응물로uspto-grants-1998_03
HRID 2066 반응식
HRID 2066반응물로uspto-grants-1998_03
HRID 2107 반응식
HRID 2107반응물로uspto-grants-1998_03
HRID 2166 반응식
HRID 2166반응물로uspto-grants-1998_03
HRID 129692 반응식
HRID 129692반응물로uspto-grants-1995_11
HRID 188659 반응식
HRID 188659생성물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 238592 반응식
HRID 238592반응물로uspto-grants-2014_02
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Solubility · 6건

greater than or equal to 100 mg/mL at 73 °F (NTP, 1992)

SOL IN 120 PARTS WATER, 35 PARTS ALC

Slightly soluble in water, soluble in acetone, ethanol, very soluble in ethyl ether

25000 mg/L @ 20 °C (exp)

slightly soluble to soluble in water; slightly soluble in alcohol; miscible in oils

1 mL in 1 mL 95% alcohol (in ethanol)

물리화학적 성질

녹는점
16 · 16-19 °C (lit.)
끓는 점
200 °C · 200 °C (lit.)
밀도
1.117 g/mL · 1.117 g/mL at 25 °C (lit.)
증기압
0.3 mm · 0.3 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.419(lit.)
FEMA
2396 · 2396 | DIMETHYL SUCCINATE
인화점
185 °F · 185 °F
저장 조건
30 °C · Store below +30°C.
용해도
75 g/L · 75g/L
물리적 상태
액체
색상
투명한
냄새
과일 같은
냄새 유형
과일 같은
생물학적 소스
synthetic
폭발한계
1 · 1.0-8.5%(V)
수용성
8.5 g/L · 8.5 g/L (20 ºC)
Merck
14 · 14,8869
JECFA Number
616 · 616
BRN
956776 · 956776
Henry's Law Constant
3 · 3.0×101 mol/(m3Pa) at 25℃, Katrib et al. (2003)
Dielectric constant
5.1 · 5.1(20℃)
안정성
안정적인. 타기 쉬운. 산화제, 산, 염기, 환원제와 호환되지 않습니다.
주요 응용
향료 및 향
화장품 원료 기능
피부 컨디셔닝 - 보습제용제향기피부 컨디셔닝
InChI
1S/C6H10O4/c1-9-5(7)3-4-6(8)10-2/h3-4H2,1-2H3
InChIKey
MUXOBHXGJLMRAB-UHFFFAOYSA-N
SMILES
COC(=O)CCC(=O)OC
LogP
0.33 at · 0.33 at 40℃
NIST
Butanedioic acid, dimethyl ester(106-65-0)
EPA
Dimethyl succinate (106-65-0)
화학적 성질 · 1건

Dimethyl succinate is colorless to light yellow liquid and has a pleasant, ethereal, winy odor and fruity, winy and burning flavor. slightly soluble in water (1%), soluble in ethanol (3%), miscible in oil. Natural product exists in fried hazelnuts. It is used as a solvent in paints, lacquers, varnishes, nitrocellulose, paint strippers, dyes, fats, photography, and waxes. It is also used in the manufacture of other succinates.

Dimethyl succinate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.

Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
EPA Safer ChemicalChemical: Dimethyl succinate
Reactivity Profile · 1건

DIMETHYL SUCCINATE reacts with acids to liberate heat along with methanol and succinic acid. May react with strong oxidizing acids to liberate enough heat to ignite the reaction products. Heat is also generated by the interaction with caustic solutions. Flammable hydrogen is generated with alkali metals and hydrides.

Air and Water ReactionsWater soluble.
Hazard Classes and Categories · 2건

Eye Irrit. 2 (36.4%)

Flammable liquids - Category 4

안전 및 보호

Fire FightingFire Extinguishing Agents: Carbon dioxide, dry chemical, alcohol foam. (USCG, 1999)
First Aid · 1건

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.

Nonfire Spill Response · 1건

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Protective Action Criteria (PAC) · 3건

16 [mg/m3]

230 [mg/m3]

1400 [mg/m3]

Personal Protective Equipment (PPE)Wear self-contained breathing apparatus, rubber boots and heavy rubber gloves. (USCG, 1999)

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 37(SRC), determined from a measured log Kow of 0.35(2) and a recommended regression-derived equation(3), indicates that dimethyl succinate is expected to have very high mobility in soil(SRC). Volatilization of dimethyl succinate from moist soil surfaces(SRC) is not expected to be important given an estimated Henry's Law constant of 6.4X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Based upon a group contribution method for predicting the probability and rate of aerobic biodegradation(5), dimethyl succinate has been estimated to be highly biodegraded with complete biodegradation occurring over a period of weeks(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 37(SRC), determined from a measured log Kow of 0.35(2) and a recommended regression-derived equation(3), indicates that dimethyl succinate is not expected to adsorb to suspended solids and sediment in water(SRC). Dimethyl succinate is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 6.4X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 1.1(3,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Based upon a group contribution method for predicting the probability and rate of aerobic biodegradation(6), dimethyl succinate has been estimated to be highly biodegraded with complete biodegradation occurring over a period of weeks(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl succinate, which has an estimated vapor pressure of 0.46 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimethyl succinate 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 about 14 days(3,SRC).

Food Survey ValuesDimethyl succinate was identified as a volatile component of roasted filberts(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Effluent ConcentrationsTrace amounts, less than 0.5 mg/l, of dimethyl succinate were detected in industrial waste samples from the Hercules, Inc. plant site near Wilmington, NC(1).
Soil Adsorption/Mobility · 1건

The Koc of dimethyl succinate is estimated as approximately 37(SRC), using a measured log Kow of 0.35(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that dimethyl succinate is expected to have very high mobility in soil(SRC).

Natural Pollution SourcesDimethyl succinate was identified as a volatile component of roasted filberts(1).
Artificial Pollution SourcesDimethyl succinate's production and use as a solvent for fruit flavors(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationBased upon a group contribution method for predicting the probability and rate of aerobic biodegradation(1), dimethyl succinate has been estimated to be highly biodegraded with complete biodegradation occurring over a period of weeks(SRC).
Environmental Bioconcentration · 1건

An estimated BCF value of 1.1 was calculated for dimethyl succinate(SRC), using a measured log Kow of 0.35(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1건

The Henry's Law constant for dimethyl succinate is estimated as 6.4X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that dimethyl succinate will be essentially nonvolatile from water surfaces(2,SRC). Dimethyl succinate's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is not expected to occur(SRC).

Non-Human Toxicity Excerpts · 2건

This study was conducted to investigate the initial tissue damage, morphogenesis, and reversibility of nasal lesions induced by the inhalation of dibasic esters. Young male rats were exposed, nose-only, to an aerosol/vapor mixture of dibasic esters at a concentration of 5,900 mg/cu m for 4 hr and subsequently killed at 1, 4, 7, 14, 21, and 42 days after exposure. Nasal lesions were distributed along major inspiratory airflow routes. Widespread epithelial denudation occurred in the anterior nasal cavity, but the lesions were confined to the dorsal meatus, adjacent the nasal septum, and the lateral middle meatus in the mid-anterior nasal cavity. The lesions were markedly less severe in the posterior nasal cavity and sharply confined to the tips of dorsal ethmoturbinates and adjacent nasal septum. The damaged cuboidal/nonciliated and respiratory epithelium in the anterior nasal cavity regained a normal structure by 4 and 7 days postexposure, respectively. The regeneration of damaged olfactory epithelium was related to the severity of initial tissue damage. Slightly damaged epithelium regained a normal appearance within 1-2 weeks, but the extensively denuded epithelium of the dorsal meatus in the anterior nasal cavity failed to regain a normal structure by 6 weeks. The sustentacular cells of the olfactory epithelium appeared to be the initial site of DBE nasal injury. In the early stages of regeneration, the epithelium was repaired by proliferating stem cells derived from basal cells. Numerous mitotic figures and bromodeoxyuridine labeling were found in the regenerating basal cells, stem cells, and sustentacular cells at 4 and 7 days. As repair processes advanced, the numbers of olfactory neurons and vesicles were increased with a proportional decrease in stem cells.

Dibasic esters are a solvent mixture of dimethyl adipate, dimethyl glutarate and dimethyl succinate which causes a selective degeneration of the nasal olfactory epithelium in rats following a 90-day inhalation exposure. In short-term cultures of rat nasal explants, it has been demonstrated that dibasic esters cytotoxicity is due to a carboxylesterase-mediated activation. In the present study, the putative toxic metabolites of dibasic esters, the monomethyl esters and the dicarboxylic acids, were evaluated in the explant system at concentrations ranging from 10 to 50 mM. Mononethyl adipate, monomethyl glutarate, and monomethyl succinate induced increases in nasal explant acid phosphatase release, a biochemical index of cytotoxicity. The nasal explant-mediated metabolism of Mononethyl adipate and monomethyl glutarate to their corresponding diacids paralleled the increases in acid phosphatase release. A carboxylesterase inhibitor, bis(p-nitrophenyl)phosphate, inhibited both the cytotoxicity and the hydrolysis of and monomethyl glutarate in the nasal explant system. The metabolism and cytotoxicity of monomethyl succinate was not attenuated as effectively by bis(p-nitrophenyl)phosphate pretreatment. Adipate, glutarate, and succinate induced concentration-related increases in cytotoxicity in the nasal explant system. These dicarboxylic acids were neither metabolized nor utilized significantly by the nasal explants. Diacid-induced cytotoxicity was not attenuated by bis(p-nitrophenyl)phosphate pretreatment. This study further established the utility of the nasal explant system for evaluating cytotoxicity of organic esters in vitro. It was established that both the monomethyl ester and diacid metabolites are cytotoxic in rat nasal explants. Finally, it was concluded that although both the monomethyl esters and the diacids contribute to the cytotoxic potential of dibasic esters in vitro, it is critical to establish if one or both of these are formed in vivo in order to identify the ultimate toxic metabolite of dibasic esters.

규제 정보

FDA Requirements · 1건

Dimethyl succinate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
WM7675000
ridadr
UN 1993
HS 번호
29171990
risk_code
36
hazard_code
Xi
safety_code
26-24/25
기존화학 물질
KE-03764
자연 발화 온도
689 °F
Hazard Classifications
Eye Irrit. 2
스토리지 클래스
10 - Combustible liquids
유해 물질 데이터
106-65-0(Hazardous Substances Data)
Cellular LocationsCytoplasm

용도 및 제조

Uses · 4건

CIR ingredient: Dimethyl Succinate

Used as a solvent for fruit flavors and a synthetic flavor; [HSDB]

SOLVENT FOR FRUIT FLAVORS

SYNTHETIC FLAVOR

U.S. Production2023: 10,000,000 - <25,000,000 lb
Consumer UsesCleaning agent
Industry UsesAdsorbent
Methods of ManufacturingBY DIRECT ESTERIFICATION OF THE ACID WITH THE ALC IN BENZENE SOLN AT THE BOIL IN THE PRESENCE OF CONCENTRATED SULFURIC ACID.
Household ProductsInformation on 21 consumer products that contain Dimethyl succinate in the following categories is provided:
Use Classification · 6건

EPA Safer Chemical Functional Use Classes -> Solvents

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4건

Plastics Material and Resin Manufacturing

Butanedioic acid, 1,4-dimethyl ester: ACTIVE

NON-ALCOHOLIC BEVERAGES 1.0-100 PPM; ICE CREAM, ICES, ETC 5.0 PPM; CANDY 15 PPM; BAKED GOODS 15 PPM; CHEWING GUM 5.0 PPM.

FEMA NUMBER 2396

응용 분야 · 3건

출처Reported found in filbert nuts and starfruit.

용도Dimethyl succinate is used as a flavoring agent. It have wide range of industrial applications such as Functional fluids (open systems), Intermediates, Paint additives and coating additives, Pigments Solvents, Viscosity adjustors.

일반 설명Colorless liquid.

제조 방법

By direct esterification of the acid with the alcohol in benzene solution at the boil in the presence of concentrated H2SO4

상·하류 제품 정보

상류 원료

Concentrated sulfuric acid메틸알콜숙신산

하류 제품

5-Methoxymethyl-2,3-pyridinedicarboxylic acidMethyl5,5,5-trifluoro-4-oxopentanoate1,4-부탄디올숙신산 디하이드라자이드석신아마이드디메틸메틸말로네이트2-(메탄올)티오펜뷰티로락톤Mono-methyl succinate숙신산무수물