유산에틸

Ethyl Lactate

HCID 7344CAS 687-47-8

기본 정보

표준 SMILES
CCOC(=O)C(C)O
InChIKey
LZCLXQDLBQLTDK-UHFFFAOYSA-N
분자식
C5H10O3
평균 분자량
118.13 g/mol
단동위원소 질량
118.06299418

개요

Ethyl lactate appears as a clear colorless liquid with a mild odor. Flash point 115 °F. Denser than water and soluble in water. Vapors heavier than air.

이름 및 식별자

우선 이름
Ethyl Lactate
IUPAC
ethyl 2-hydroxypropanoate
현지명
에틸-L-젖산염
영어명
Ethyl L(-)-lactate
분자식
C5H10O3
분자량
118.13

이름 및 동의어

ETHYL LACTATE97-64-3Ethyl 2-hydroxypropanoateSolactolActylolAcytolEthyl 2-hydroxypropionatePropanoic acid, 2-hydroxy-, ethyl esterLactate d'ethyle2-Hydroxypropanoic acid ethyl esterEthyl alpha-hydroxypropionateFEMA No. 2440
이름 더 보기
락트산-L-에틸에틸(S)-(-)-젖산(ETHYL락트산에틸에틸(S)-(-)-젖산(ETHYL(S)-(-)-LACTATE)(-)-에틸 2-하이드록시프로파노에이트(2S)-2-하이드록시프로판산, 에틸 에스터(S)-2-하이드록시프로피온산 에틸(S)-2-하이드록시프로피온산, 에틸 에스터2-하이드록시프로피온산, 에틸 에스터L-(-)-락트산 에틸 (PICCS)락트산 에틸알파-하이드록시프로피온산 에틸ETHYL (S)-(-)-LACTATEEthyl (S)-2-hydroxypropanoateL-Ethyl LactateETHYL L-LACTATE(S)-(-)-ETHYL LACTATE(S)-Ethyl 2-hydroxypropanoate(-)-ETHYL (S)-2-HYDROXYPROPIONATEETHYL-(S)-LACTATEethyl (2S)-lactateEthyl L-lactate 99%
Ethylester kyseliny mlecneDTXSID6029127F3P750VW8IPURASOLV ELSVERTECBIO ELNSC-8850DTXCID509127CHEBI:78321

데이터베이스 식별자

CAS
687-47-8、97-64-3
PubChem CID
7344
DTXSID
DTXSID6029127
ChEMBL
CHEMBL3186323
ChEBI
CHEBI:78321
UNII
F3P750VW8I
EC Number
202-598-0
Nikkaji
J4.732E

물성

구조 계산 물성

XLogP
0.2
극성 표면적
46.5 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
3
무거운 원자 수
8

실험 및 물리화학적 성질

Chemical ClassesFlammable agents - 2nd degree
SolventsSolvents -> Esters (<C12)
Cosmetics · 2건

Cosmetic ingredients (Ethyl Lactate) -> CIR (Cosmetic Ingredient Review)

Solvent

FragrancesFragrance Ingredient (Ethyl lactate) -> IFRA transparency List
Odor · 2건

Buttery odor

Fruity butterscotch

Taste · 2건

Sweet, fruity, creamy and pineapple like taste

Milk cream taste

물리화학적 성질

녹는점
26 °C · −26 °C(lit.)
끓는 점
154 °C · 154 °C(lit.)
밀도
1.034 g/mL · 1.034 g/mL at 20 °C(lit.)
증기 밀도
4.1 · 4.1 (vs air)
증기압
2 mm · 2 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.4130(lit.)

화학적 성질

clear liquid

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P354+P338, P317, P319, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2851) of reports.

Danger

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

유해성 정보

Regulatory Information · 6건

Chemical: Propanoic acid, 2-hydroxy-, ethyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Propanoic acid, 2-hydroxy-, ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanoic acid, 2-hydroxy-, ethyl 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: 28-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/28375

Propanoic acid, 2-hydroxy-, ethyl ester: HSNO Approval: HSR001150 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 - Propanoic acid, 2-hydroxy-, ethyl ester: Human health tier II assessment
DOT LabelFlammable Liquid
Fire Hazards · 2건

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

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

Fire PotentialModerate fire risk.
Health Hazards · 2건

Inhalation of concentrated vapor may cause drowsiness. Contact with liquid causes mild irritation of eyes and (on prolonged contact) skin. Ingestion may cause narcosis. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

안전 및 보호

Fire FightingExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
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

INHALATION: remove victim to fresh air.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 3건

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray to cool unopened containers.

Storage ConditionsKeep well closed.

독성 정보

Ecotoxicity Values · 2건

EC50; Species: Daphnia magna (Water Flea); Conditions: freshwater, static, 20 °C, pH 8.0; Concentration: 560000 ug/L for 48 hr (95% confidence interval: 560000-763000 ug/L); Effect: intoxication, decreased mobility /97% purity/

LC50; Species: Danio rerio (Zebra Danio); Conditions: freshwater, static; Concentration: 320000 ug/L for 96 hr (95% confidence interval: 305000-417000 ug/L) /97% purity/

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that ethyl lactate is expected to have very high mobility in soil(SRC). Volatilization of ethyl lactate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-7 atm-cu m/mole(SRC), based upon its vapor pressure, 3.75 mm Hg(3), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(4). Ethyl lactate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Ethyl lactate exhibited 22% and 75% theoretical BOD in 5 and 28 days, respectively, using a Closed Bottle screening test(5), suggesting biodegradation may be an important fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that ethyl lactate 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 5.8X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 3.75 mm Hg(4), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(5). Hydrolysis is expected in water based on estimated hydrolysis half-lives of 72 and 7 days at pH 7 and 8, respectively(2). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of -0.18(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Ethyl lactate exhibited 22% and 75% theoretical BOD in 5 and 28 days, respectively, using a Closed Bottle screening test(7), suggesting biodegradation may be an important fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl lactate, which has a vapor pressure of 3.75 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl lactate 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 4.1 days(SRC), calculated from its rate constant of 3.9X10-12 cu cm/molecule-sec at 23 °C(3). Ethyl lactate does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1건

Ethyl lactate was identified as a volatile component in soy sauce and Sukiyaki(1). Ethyl lactate was identified as a flavor component of Pine Sprout Tea(2). Ethyl lactate was identified as a volatile component of three commercial fermented soybean curds at concentrations of 9744.4, 5084.5 and 2755.7 ug/kg(3). Ethyl lactate is reported in apple, apricot, grape, pineapple, raspberry, plum, blackberry, cabbage, beer, cognac, rum, whiskey, sherry, grape wines, fruit brandies, vinegar, rye and wheat bread, butter, and soy sauce(4). Ethyl lactate is also reported in citrus fruits, peas, sauerkraut, bread preferment, cider, cocoa and Bantu beer(5). Ethyl lactate concentrations increased steadily with fermentation age in Gueuze beer(6). Ethyl lactate was produced in wines made from Early Richmond cherries fermented with six yeast varieties of Saccharomyces cerevisiae(7). Ethyl lactate was detected in the fruit juice of yellow passion fruit (Passiflora edulis Sims G. Glavicarpa degner)(8).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity Summary · 3건

Based on the available information included in this report, the CIR Expert Panel concludes that Glycolic and Lactic Acid, their common salts and their simple esters, are safe for use in cosmetic products at concentrations less than or equal to 10%, at final formulation pH greater than or equal to 3.5, when formulated to avoid increasing sun sensitivity or when directions for use include the daily use of sun protection. These ingredients are safe for use in salon products at concentrations less than or equal to 30%, at final formulation pH greater than or equal to 3.0, in products designed for brief, discontinuous use followed by thorough rinsing from the skin, when applied by trained professionals, and when application is accompanied by directions for the daily use of sun protection...Ethyl Lactate...

Safe for use in cosmetics, with qualifications

IDENTIFICATION AND USE: Ethyl lactate is a colorless liquid with a buttery or fruity odor and a sweet, fruity taste. It is used as a solvent for nitrocellulose, cellulose acetate, many cellulose ethers, resins. It is also the active ingredient in many antiacne preparations; and used in the preparation of lacquers, paints, enamels, varnishes, stencil sheets, safety glass, flavoring, and cosmetic formulations (0.2%). HUMAN EXPOSURE AND TOXICITY: Etyl lactate was not a skin irritant or skin sensitizer in humans, when tested at 8% in petroleum. In a separate human study, ethyl lactate applied to the skin significantly reduced skin pH, the number of bacteria recoverable from skin, and the hydrolysis of sebum to free fatty-acid by bacterial lipases. ANIMAL STUDIES: Ethyl lactate is irritating to the rabbit eye and guinea pig skin (intradermal injections). It is a central nervous system depressant and lethal to animals in high concentrations, causing respiratory paralysis. One out of 8 rats died when fed a diet containing 5% ethyl lactate. No evidence of teratogenicity or maternal toxicity was observed in the testing of other lactate esters. Ethyl lactate was applied percutaneously on the back of groups of pregnant rats on days 6 to 15 of gestation. Applied doses were 0, 517, 1551, or 3619 mg/kg bw. Slight erythema and desquamation was observed in treated animals at the application site. No other clinical signs or necropsy observations were noted. No effects were observed on the development. Ethyl lactate was negative for mutagenicity in the Ames test using strains TA 98, 100, 1535, 1537, and 1538.

Plant ConcentrationsEthyl lactate has been detected, not quantified in pineapple fruit (Ananas comosus; Bromeliaceae)(1).

규제 정보

FDA Requirements · 3건

Ethyl lactate 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: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Ethyl lactate is an indirect food additive for use only as a component of adhesives.

The following diluents may be safely used in color additive mixtures that are exempt from certification and which are to be used for coloring drugs, subject to the condition that each straight color in the mixture has been exempted from certification or, if not so exempted, is from a batch that has previously been certified and has not changed in composition since certification. ... Ethyl lactate: special use, inks for branding pharmaceutical forms.

FIFRA Requirements · 1건

Unless specifically excluded, residues resulting from the use of the following substance as either an inert or an active ingredient in a pesticide chemical formulation, including antimicrobial pesticide chemicals, is exempted from the requirement of a tolerance under FFDCA section 408, if such use is in accordance with good agricultural or manufacturing practices. Lactic acid, ethyl ester is included on this list.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
OD5075000
ridadr
UN 1192 3/PG 3
독성
LD50 orally in Rabbit: > 2000 mg/kg
HS 번호
29181100

화학 및 산업

약리 정보

Metabolism/Metabolites · 2건

Whole bovine olfactory & respiratory mucous membranes did not hydrolyze acetylcholine in vitro, but mitochondrial fractions of both tissues had weak esterase activity with this substrate. The tissues or mitochondrial fractions rapidly attacked a series of other esters, such as ethyl lactate. The esterase activity of olfactory mucous membrane was 10-fold greater than that of the respiratory one against most of the esters, but was only 2-fold greater against ethyl butyrate. The 2 tissues had only weak ATPase activity. The esterase & ATPase systems may play a role in the biochemical mechanism of olfaction.

Ethyl lactate was shown to be hydrolyzed to ethanol & lactic acid in serum & when applied to human skin.

Absorption, Distribution and Excretion · 1건

In an experiment to determine biochemical effects in skin tissue, ethyl [(14)C] lactate was applied to the dorsal skin of female rats. Analysis of autoradiographic images indicated that (14)C had accumulated in sebaceous glands & hair follicles.

Cellular LocationsCytoplasm

용도 및 제조

Uses · 6건

CIR ingredient: Ethyl Lactate

Used as a solvent substitute for glycol ethers in photolithography in the semiconductor manufacturing industry; used in some nail polish removers; [Sullivan, p. 450-1] Used as a solvent for resins, dyes, and coatings; has FDA approval for use as a food flavoring agent; [HSDB]

Semiconductor Manufacturing [Category: Industry]

Solvent for nitrocellulose, cellulose acetate, many cellulose ethers, resins; lacquers; paints; enamels; varnishes; stencil sheets; safety glass; flavoring.

To reduce the alkalinity of cosmetic formulations.

Reported uses (ppm):

U.S. Production · 3건

2023: 1,000,000 - <2,500,000 lb

Propanoic acid, 2-hydroxy-, ethyl ester is listed as a High Production Volume (HPV) chemical (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).

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Propanoic acid, 2-hydroxy-, ethyl ester. National Production Volume: 1,000,000 - 10,000,000 lb/yr.

Consumer UsesEtching agent
Industry UsesAdhesion/cohesion promoter
Methods of Manufacturing · 2건

Derivation: (a) By the esterification of lactic acid with ethanol; (b) by combining acetaldehyde with hydrogen cyanide to form acetaldehyde cyanohydrin, which is converted into ethyl lactate by treating with ethanol and an inorganic acid.

d-Ethyl lactate is obtained from d-lactic acid by azeotropic distillation with ethyl alcohol or benzene in the presence of concentrated H2SO4; the l-form is prepared in similar fashion starting from l-lactic acid; the racemic product is prepared by boiling for 24 hours optically inactive lactic acid with ethyl alcohol in carbon tetrachloride, or with an excess of ethyl alcohol in the presence of chlorosulfonic acid, or in the presence of benzenesulfonic acid in benzene solution.

Formulations/PreparationsGrades: Technical (96%).
응용 분야 · 2건

용도(-)-Ethyl L-Lactate is a naturally occuring chemical compound that is often used as an industrial solvent in chemical reactions.

일반 설명Ethyllactate is an economically viablegreen solvent used in organic synthesis. It is generally employed in organic reactions like multi-component reactions, cycloaddition reaction, asymmetric induction, photochemical synthesis, and ligand-free coupling reactions, etc.

공급사50 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

추가 설명

정의ChEBI: The (2S)-enantiomer of ethyl lactate.

관련 반응

129건

연결된 노트

불러오는 중…