2-Propenoic acid, 3-phenyl-, phenylmethyl ester
CINNAMEIN · 2-Propenoic acid, 3-phenyl-, phenylmethyl ester · FEMA 2142 · guisuanbianzhi · Benzyl ciamate · Benzyl cinmate · BENZYL CINNAMATE · Benzylcinnamoate
Identifiers & Physical Properties
| CAS No. | 103-41-3 |
|---|---|
| Molecular formula | C16H14O2 |
| Average molar mass | 238.28 g/mol |
| Monoisotopic mass | 238.09937969 g/mol |
| SMILES | O=C(C=Cc1ccccc1)OCc1ccccc1 |
| InChIKey | NGHOLYJTSCBCGC-UHFFFAOYSA-N |
| PubChem CID | 7652 |
| ChEMBL | CHEMBL2361576 |
| DTXSID | DTXSID3041663 |
Chemical & Physical Properties
| XLogP | 3.8 |
|---|---|
| Topological polar surface area | 26.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 5 |
| Heavy atoms | 18 |
| Formal charge | 0 |
| Complexity | 271 |
| 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 | BENZYL CINNAMATE |
| Refractive index | 1.4025-1.4045 |
| FLAVIS Number | 09.738 | Benzyl cinnamate |
| Flash point | >230 °F |
| Storage conditions | Store below +30°C. |
| Solubility | alcohol: soluble(lit.)PRACTICALLY INSOLUBLE |
| Physical state | Crystalline Mass or Liquid After Melting |
| Color | Clear colorless to yellow |
| Odor | aromatic odor |
| Odor type | balsamic |
| Biological source | synthetic |
| Merck | 14,1130 |
| JECFA Number | 670 |
| BRN | 2051339 |
| Henry's law constant | 3.0×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| Cosmetics Ingredients Functions | PERFUMING |
| InChI | 1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11+ |
| InChIKey | NGHOLYJTSCBCGC-VAWYXSNFSA-N |
| SMILES | O=C(OCC1=CC=CC=C1)/C=C/C2=CC=CC=C2 |
| LogP (partition coefficient) | 4.18 at 23.7℃ |
| CAS DataBase Reference | 103-41-3(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | BENZYL CINNAMATE |
| FDA 21 CFR | 172.515 |
| EWG's Food Scores | 2-5 |
| FDA UNII | V67O3RO97U |
| NIST Chemistry Reference | Benzyl cinnamate(103-41-3) |
| EPA Substance Registry System | Benzyl cinnamate (103-41-3) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07,GHS09 |
| Signal word | Warning |
| GHS hazard statements | H317-H410 |
| GHS precautionary statements | P261-P272-P273-P280-P302+P352-P333+P313 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 22-24/25 |
| UN transport number | 3077 |
| Water hazard class (WGK) | 2 |
| RTECS number | GD8400000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29163900 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Aquatic Acute 1Aquatic Chronic 2Skin Sens. 1B |
| Hazardous substances data | 103-41-3(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 5530 mg/kg (Jenner) |
| REACH registrations | Active |
Safety & Regulations
| Regulatory information | Chemical: 2-Propenoic acid, 3-phenyl-, phenylmethyl esterHazard Traits - Fragrance AllergenAuthoritative List - Annex III of the EU Cosmetics Regulation No. 1223/2009 - Fragrance AllergensReport - if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)Benzyl cinnamate: Does not have an individual approval but may be used under an appropriate group standard |
|---|---|
| Other safety information | IMAP assessments - Chemicals with limited data availability that are used in fragrances: Human health tier II assessment |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | GD8400000 |
| UN transport number | 3077 |
| Customs code | 29163900 |
| Toxicity | LD50 orally in rats: 5530 mg/kg (Jenner) |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07,GHS09 |
| Safety statements (S) | 22-24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H317-H410 |
| REACH registrations | Active |
| Hazard class | Aquatic Acute 1Aquatic Chronic 2Skin Sens. 1B |
Applications & Uses
Occurrence
Reported found in Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam.
Uses
Benzyl cinnamate has been employed as internal standard during the determination of compounds commonly added to personal care products such as UV filters and antimicrobial agents in environmental samples.
Uses
Mild. sweet-balsamic and somewhat floral odor of great tenacity. Used quite frequently in perfumery, mainly as a fixative, and particularly in perfumes for Talcum (powders). It blends well with floral bases, spicy fragrances and Ambre types.Used in flavor compositions for imitation Apricot, Cherry, Chocolate, Honey, Peach, Pineapple, Liquor, Raspberry, Rum, Prune, etc.Concentration may be little more than traces, usually about 6 ppm, except in chewing gum: up to 125 ppm.
General Description
Benzyl cinnamate is widely used as a fragrance ingredient.
Preparation & Synthesis
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.