Benzyl cinnamate
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Benzyl cinnamate
structure -
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CAS No:
103-41-3
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Formula:
C16H14O2
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Chemical Name:
Benzyl cinnamate
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Synonyms:
2-Propenoic acid,3-phenyl-,phenylmethyl ester;Cinnamic acid,benzyl ester;Benzyl cinnamate;Benzyl γ-phenylacrylate;Cinnamein;Benzyl 3-phenylpropenoate;3-Phenyl-2-propenoic acid benzyl ester;NSC 11780;NSC 44403;NCCF 1500;NCCF 300;NCCF 100;NCCF 4000;8014-16-2
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CAS No:
Description
Benzyl cinnamate, occurs in Balsam of Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam, is used in heavy oriental perfumes and as a fixative[1].
White to pale yellow solid
Benzyl cinnamate Basic Attributes
238.28
238.28
2051339
203-109-3
DTXSID3041663
WHITE TO PALE-YELLOW, FUSED, CRYSTALLINE SOLID|Crystals from 95% ethanol|White crystals
29163900
Characteristics
26.3
3.44320
Clear colorless to yellow Crystalline Mass or Liquid After Melting
1.109 g/cm3 @ Temp: 15 °C
39 °C
228-230 °C @ Press: 22 Torr
>230 °F
1.4025-1.4045
Practically insoluble in water
2-8°C
1.00e-05 mmHg
Oral-rat LDL0: 5530 mg/kg; Oral-guinea pig LD50; 3760 mg/kg
More flammable liquid; heat breaks down to stimulate smoke
Sweet odor of balsam
HONEY-LIKE TASTE
CONGEALING POINT: 33.0-34.5 °C; ACID VALUE: NOT MORE THAN 1.0|Decomposes on distillation @ ordinary pressure
Safety Information
3077
2
36/37/38
22-24/25
GD8400000
Ventilated, low temperature and dry
Has mild allergic reaction and skin irritation
MELTS AT ROOM TEMPERATURE TO YELLOWISH LIQUID
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.
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.
|Warning|H317 (99.82%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 1704 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
SLIGHT; WHEN HEATED
... MAY BE MILDLY IRRITATING TO THE SKIN. /BALSAM PERU/
Toxicity
moderately toxic
LD50 Rat oral 5.38 g/kg
/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).
Benzyl 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).
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).
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).
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).
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.
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).
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).
Drug Information
TOXICITY RATINGS: 3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMANS) 0.5-5 G/KG; BETWEEN 1 OZ AND 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB). /CINNAMIC ACID ESTERS/
... MAY BE MILDLY IRRITATING TO THE SKIN. IT HAS BEEN INGESTED AND EVEN INJECTED IV WITHOUT ILL EFFECTS. /BALSAM PERU/
Benzyl cinnamate Use and Manufacturing
Generally made from benzyl alcohol and cinnamate. It is made by excessive heat of sodium laurate and benzyl chloride in water to 110~115℃. By sodium laurate and excess benzyl chloride in the presence of diethylamine co-heating.
In artificial flavors, in perfumes, mainly as a fixative.
ASSAY: 99% MINIMUM|Grades: Technical; FCC
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
THIN-LAYER CHROMATOGRAPHY STUDY OF THE COMPONENTS OF CABREUVA BALSAM.|TWO TECHNIQUES FOR CONTROL OF PERUVIAN BALSAM IN OINTMENTS ARE DESCRIBED: 1) THIN-LAYER CHROMATOGRAPHY; 2) GAS CHROMATOGRAPHIC DETERMINATION OF THE 2 ESTERS WAS METHOD OF CHOICE.
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Masking
Flavoring Agents
Computed Properties
Molecular Weight:238.28
XLogP3:3.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:238.099379685
Monoisotopic Mass:238.099379685
Topological Polar Surface Area:26.3
Heavy Atom Count:18
Complexity:271
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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