| Identification | More | [Name]
Benzyl cinnamate | [CAS]
103-41-3 | [Synonyms]
BENZYL B-PHENYLACRYLATE
BENZYL CINNAMATE
BENZYL TRANS-3-PHENYLPROPENOATE
CINNAMEIN
CINNAMIC ACID BENZYL ESTER
FEMA 2142
2-Propenoic acid, 3-phenyl-, phenylmethyl ester
2-Propenoicacid,3-phenyl-,phenylmethylester
3-Phenyl-2-propenoic acid phenylmethyl ester
3-phenyl-2-propenoicacidphenylmethylester
3-phenyl-2-propenoicaciphenylmethylester
Benzyl (2E)-3-phenyl-2-propenoate
Benzyl 3-phenylpropenoate
Benzyl alcohol cinnamic ester
Benzyl alcohol, cinnamate
Benzyl gamma-phenylacrylate
benzyl-3-phenylpropenoate
benzylalcohol,cinnamate
benzylalcohol,cinnamicester
benzylbeta-phenylacrylate | [EINECS(EC#)]
203-109-3 | [Molecular Formula]
C16H14O2 | [MDL Number]
MFCD00004789 | [Molecular Weight]
238.28 | [MOL File]
103-41-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless to yellowish crystalline mass or liquid after meltin | [Melting point ]
34-37 °C (lit.) | [Boiling point ]
195-200 °C/5 mmHg (lit.) | [density ]
1.11 | [vapor pressure ]
<0.1 hPa (20 °C) | [FEMA ]
2142 | [refractive index ]
1.4025-1.4045
| [Fp ]
>230 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
alcohol: soluble(lit.) | [form ]
Crystalline Mass or Liquid After Melting | [color ]
Clear colorless to yellow | [Odor]
aromatic odor | [Odor Type]
balsamic | [Water Solubility ]
PRACTICALLY INSOLUBLE | [JECFA Number]
670 | [Merck ]
14,1130 | [BRN ]
2051339 | [LogP]
4.18 at 23.7℃ | [CAS DataBase Reference]
103-41-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzyl cinnamate(103-41-3) | [EPA Substance Registry System]
Benzyl cinnamate (103-41-3) |
| Safety Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
3077 | [WGK Germany ]
2
| [RTECS ]
GD8400000
| [TSCA ]
Yes | [HS Code ]
29163900 | [Hazardous Substances Data]
103-41-3(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 5530 mg/kg (Jenner) |
| Hazard Information | Back Directory | [Hazard]
Moderately toxic. | [Chemical Properties]
Benzyl cinnamate has a sweet, balsamic odor and a honey-like taste. | [Chemical Properties]
Benzyl Cinnamate occurs in
balsams and balsam oils. It forms white, sweet-balsamic-smelling crystals (mp
35-36°C). Benzyl cinnamate is used as a fixative in perfumes and as a component
of heavy, oriental perfumes. | [Chemical Properties]
Clear colorless to yellowish crystalline mass or liquid after meltin | [Occurrence]
Reported found in Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of
copaiba balsam. | [Uses]
In artificial flavors, in perfumes, mainly as a fixative. | [Definition]
ChEBI: 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 antigen and an epitope. | [Preparation]
By heating benzyl chloride and excess sodium cinnamate in water to 100 to 115°C; by heating sodium cinnamate with an
excess of benzyl chloride in the presence of diethylamine. | [Production Methods]
Benzyl cinnamate is produced by the direct esterification of
benzyl alcohol with cinnamic acid. | [Taste threshold values]
Taste characteristics at 50 ppm: spicy, floral, fruity, balsamic. | [General Description]
Benzyl cinnamate is widely used as a fragrance ingredient. | [Flammability and Explosibility]
Nonflammable | [Safety Profile]
Moderately toxic by ingestion. Amild allergen and skin irritant. Combustible liquid. When heated to decomposition it emits acridsmoke and irritating fumes. | [target]
Immunology & Inflammation related | [Metabolism]
See monograph on Benzyl alcohol (p. 1011). | [Purification Methods]
Recrystallise the ester to a constant melting point from 95% EtOH. It has the odour of balsam. Alternatively dissolve it in Et2O, wash it with 10% aqueous Na2CO3, H2O, dry (Na2SO4), evaporate and fractionate it under reduced pressure using a short Vigreux column (p 11). It decomposes when boiled at atmospheric pressure. [Eliel & Anderson J Am Chem Soc 74 547 1952, Bender & Zerner J Am Chem Soc 84 2550 1962, Beilstein 9 IV 2012.] |
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