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2-프로펜산,3-페닐-,페닐메틸에스테르,(2E)-

Benzyl Cinnamate

HCID 5273469
새 노트새 반응견적 요청하기인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
103-41-3
표준 SMILES
O=C(/C=C/c1ccccc1)OCc1ccccc1
InChIKey
NGHOLYJTSCBCGC-VAWYXSNFSA-N
분자식
C16H14O2
평균 분자량
238.28 g/mol
단동위원소 질량
238.09937969

개요

Benzyl cinnamate is the cinnamate ester derived from cinnamic acid and benzyl alcohol. Occuring in Balsam of Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam, it is used in heavy oriental perfumes, as a fixative and as a flavouring agent. It has a role as a flavouring agent, a fragrance, a fixative, an epitope and an antigen.

이름 및 식별자

우선 이름
Benzyl Cinnamate
IUPAC
benzyl (E)-3-phenylprop-2-enoate
현지명
2-프로펜산,3-페닐-,페닐메틸에스테르,(2E)-
영어명
2-Propenoic acid, 3-phenyl-, phenylMethyl ester, (2E)-
분자식
C16H14O2
분자량
238.28

이름 및 동의어

BENZYL CINNAMATE103-41-3CinnameinBenzyl 3-phenylpropenoatebenzyl (E)-3-phenylprop-2-enoatetrans-Cinnamic acid benzyl esterCinnamic acid, benzyl esterBenzyl alcohol, cinnamic esterFEMA No. 2142Benzyl gamma-phenylacrylateBenzylcinnamateBenzylester kyseliny skoricove
이름 더 보기
2-프로펜산,3-페닐-,페닐메틸에스테르,(2E)-2-Propenoic acid, 3-phenyl-, phenylMethyl ester, (2E)-
Benzyl-3-phenylpropenoate3-Phenyl-2-propenoic acid phenylmethyl esterV67O3RO97UCHEBI:146174DTXCID1021663NSC-11780NSC-44403DTXSID3041663

데이터베이스 식별자

CAS
103-41-3、78277-23-3
PubChem CID
5273469
DTXSID
DTXSID00880905
ChEMBL
CHEMBL361197
ChEBI
CHEBI:146174
UNII
V67O3RO97U
EC Number
203-109-3、884-588-1

물성

구조 계산 물성

XLogP
3.8
극성 표면적
26.3 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
5
무거운 원자 수
18
형식 전하
0
복잡도
271

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Esters, Other
Cosmetics · 2건

Cosmetics ingredient -> Base; Flavor; Fragrance; Other (Specify)

Masking

SpringerMaterials PropertiesViscosity
FragrancesFragrance Ingredient (Benzyl cinnamate) -> IFRA transparency List
OdorSweet odor of balsam
TasteHONEY-LIKE TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2건

1.109 AT 15 °C

PRISMS; SADTLER REFERENCE NUMBER: 1520 (IR, PRISM); 430 (UV); 104 (NMR); DENSITY: 1.109 @ 15 °C /TRANS/

Flavoring AgentsEU Flavoring substances
Color/Form · 3건

WHITE TO PALE-YELLOW, FUSED, CRYSTALLINE SOLID

Crystals from 95% ethanol

White crystals

Solubility · 4건

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Warning

H317 (99.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1794 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 5건

Chemical: 2-Propenoic acid, 3-phenyl-, phenylmethyl ester

Hazard Traits - Fragrance Allergen

Regulation (EC) No 1831/2003 (amended)

REACH registered substance: Benzyl cinnamate (EC: 203-109-3)

Benzyl cinnamate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Chemicals with limited data availability that are used in fragrances: Human health tier II assessment
Fire PotentialSLIGHT; WHEN HEATED
Hazards Summary · 1건

Safe when used as a flavoring agent in food; [JECFA] Mild skin irritant; Causes somnolence and coma in lethal concentration studies; [RTECS] Included in list of established contact allergens in humans; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)]

FDA Requirements · 1건

Benzyl cinnamate 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.

화학 및 산업

용도 및 제조

Uses · 3건

Constituent of storax, Peru, and Tolu balsams; [Merck Index] Used in flavors and perfumes; [HSDB]

In artificial flavors, in perfumes, mainly as a fixative

Fixative in perfumes and as a component of heavy, oriental perfumes.

IFRA Fragrance Standards · 6건

Benzyl cinnamate

Benzyl γ-phenylacrylate; Benzyl 3-phenylpropenoate; Cinnamein; Cinnamic acid, benzyl ester; Phenylmethyl 3-phenyl-2-propenoate; 2-Propenoic acid, 3-phenyl-phenylmethyl ester

IFRA_STD_010.pdf

49

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

Restriction: This material should be used only in the limited quantity as stated in the Standard

Methods of Manufacturing · 5건

USUALLY PREPARED BY ESTERIFICATION OF BENZYL ALCOHOL AND CINNAMIC ACID.

BY HEATING BENZYL CHLORIDE AND EXCESS SODIUM CINNAMATE IN WATER TO 110-115 °C...

BY HEATING SODIUM CINNAMATE WITH EXCESS OF BENZYL CHLORIDE IN PRESENCE OF DIETHYLAMINE.

Prepn: Volwiler, Vliet, J Am Chem Soc 43, 1672 (1921); Eliel, Anderson, J Am Chem Soc 74, 547 (1952); Bender, Zerner, J Am Chem Soc 84, 2550 (1962).

Prepared by esterification of benzyl alcohol with cinnamic acid

Formulations/Preparations · 2건

ASSAY: 99% MINIMUM

Grades: Technical; FCC

Household Products · 2건

Cosmetics product ingredient: 2-Propenoic acid, 3-phenyl-, phenylmethyl ester (BENZYL CINNAMATE)

Information on 37 consumer products that contain Benzyl Cinnamate in the following categories is provided:

Use Classification · 5건

Fragrance Ingredients

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Cosmetics -> Masking

General Manufacturing Information

공급사

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공개 문의

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Nikkaji
J106.759A、J5.016D

1:8 IN 90% ALCOHOL

Practically insol in water, propylene glycol and glycerin. Sol in alcohol, ether, oils.

insoluble in water; soluble in oils

very soluble (in ethanol)

Flash PointGREATER THAN 100 °C

물리화학적 성질

녹는점
39 °C · 39°C
끓는 점
340.88 °C · 340.88°C (rough estimate)
밀도
1.109 · 1.1090
굴절률
1.629 · 1.6290 (estimate)
Hazard Classes and CategoriesSkin Sens. 1B (99.8%)
Skin, Eye, and Respiratory Irritations... MAY BE MILDLY IRRITATING TO THE SKIN. /BALSAM PERU/

안전 및 보호

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.

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10,400(SRC), determined from a structure estimation method(2), indicates that benzyl cinnamate is expected to be immobile in soil(SRC). Volatilization of benzyl cinnamate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.3X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Benzyl cinnamate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1X10-5 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10,390(SRC), determined from a structure estimation method(2), indicates that benzyl cinnamate is 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 3.3X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A base-catalyzed second-order hydrolysis rate constant of 3.8X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(5); this corresponds to half-lives of 6 years and 211 days at pH values of 7 and 8, respectively(5). According to a classification scheme(6), an estimated BCF of 269(SRC), from an estimated log Kow of 4.06(7) and a regression derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzyl cinnamate, which has an estimated vapor pressure of 1X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase benzyl cinnamate 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 for the cis-isomer and 13 hours for the trans-isomer of benzyl cinnamate(SRC), calculated from their rate constants of 28X10-12 and 31X10-12 cu cm/molecule-sec at 25 °C, respectively(SRC), determined using a structure estimation method(3). Particulate-phase benzyl cinnamate may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc for benzyl cinnamate can be estimated to be 10,400(SRC). According to a classification scheme(2), this estimated Koc value suggests that benzyl cinnamate is expected to be immobile in soil.

Natural Pollution Sources · 3건

/IT IS/ REPORTED FOUND IN PERU AND TOLU BALSAM, IN SUMATRA AND PENANG BENZOIN, AND AS MAIN CONSTITUENT OF COPAIBA BALSAM.

PERUVIAN OR INDIAN BALSAM...CONSISTS CHIEFLY OF (50-60%) OF ESTERS OF CINNAMIC AND BENZOIC ACIDS, ESPECIALLY CINNAMEIN (BENZYL CINNAMATE). /BALSAM PERU/

Benzyl cinnamate is found in balsams of Peru, Tolu, Styrax, Copaiba and others(1).

Human Toxicity Excerpts... MAY BE MILDLY IRRITATING TO THE SKIN. IT HAS BEEN INGESTED AND EVEN INJECTED IV WITHOUT ILL EFFECTS. /BALSAM PERU/
Artificial Pollution SourcesBenzyl cinnamate's production and use in artificial flavors and perfumes(1), may result in its release to the environment through various waste streams and result in consumer exposure(SRC).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1건

An estimated BCF of 270 was calculated for benzyl cinnamate(SRC), using an estimated log Kow of 4.1(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

Volatilization from Water/Soil · 1건

The Henry's Law constant for benzyl cinnamate is estimated as 3.3X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that benzyl cinnamate is expected to be essentially nonvolatile from water surfaces(2). Benzyl cinnamate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may not occur(SRC). Benzyl cinnamate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1X10-5 mm Hg(3).

Non-Human Toxicity ExcerptsMild dermal irritant.
Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of benzyl cinnamate with photochemically-produced hydroxyl radicals has been estimated as 28X10-12 cu cm/molecule-sec at 25 °C for its cis-isomer and 31X10-12 cu cm/molecule-sec at 25 °C for its trans-isomer(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 14 and 13 hours for the cis and trans-isomers, respectively, at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 3.8X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 6 years and 211 days at pH values of 7 and 8, respectively(2).

Probable Routes of Human Exposure · 1건

NIOSH (NOES Survey 1981-1983) has statistically estimated that 2855 workers (1107 of these are female) are potentially exposed to benzyl cinnamate in the US(1). Occupational exposure to benzyl cinnamate may occur through inhalation and dermal contact with this compound at workplaces where benzyl cinnamate is produced or used(SRC).

규제 정보

FDA Requirements · 1건

Benzyl cinnamate 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.

· 5건

2-Propenoic acid, 3-phenyl-, phenylmethyl ester: ACTIVE

USED IN NON-ALCOHOLIC BEVERAGES @ 1.4 PPM; IN ICE CREAM, ICES, ETC @ 2.5 PPM; IN CANDY @ 6.7 PPM; IN BAKED GOODS @ 6.6 PPM; IN GELATINS & PUDDINGS @ 3.0-5.0 PPM; IN CHEWING GUM @ 5.3-120 PPM.

BENZYL CINNAMATE IS USED AS FIXATIVE OR MODIFIER IN SPICY PRODUCTS AND LIQUOR. IT HAS A GOOD STABILITY RATING.

BENZYL CINNAMATE WAS ONE OF VARIOUS PROTECTANTS THAT REDUCED SUNLIGHT INACTIVATION & PROLONGED THE VIABILITY OF BACILLUS THURINGIENSIS SPORES & SPRUCE BUDWORM NUCLEAR POLYHEDROSIS VIRUS FOR MORE THAN 7 DAYS.

FEMA NUMBER 2142

Restriction Limits in the Finished Product (%) · 6건

0.36 [Products applied to the lips]

0.11 [Products applied to the axillae]

1.2 [Products applied to the face/body using fingertips]

2 [Products related to fine fragrances]

0.51 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0.51 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]