CINNAMYL FORMATE Chemical Properties

Boiling point:

250-254 °C (lit.)

Density 

1.08 g/mL at 25 °C (lit.)

vapor pressure 

2.666Pa at 25℃

refractive index 

n20/D 1.553(lit.)

FEMA 

2299 | CINNAMYL FORMATE

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

Odor

at 100.00 %. balsam fruity floral green herbal cinnamyl narcissus

Odor Type

balsamic

biological source

synthetic

Water Solubility 

725.1mg/L at 25℃

JECFA Number

649

LogP

2.3 at 25℃

EPA Substance Registry System

2-Propen-1-ol, 3-phenyl-, formate (104-65-4)

Safety Information

WGK Germany 

2

RTECS 

UD5530000

Toxicity

The acute oral LD₅₀ in rats was reported as 2.9 g/kg (2.38-3.54 g/kg) and the acute dermal LD₅₀ in rabbits as > 5 g/kg (Denine. 1973).

MSDS

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CINNAMYL FORMATE Usage And Synthesis

Chemical Properties

Cinnamyl formate has a balsamic, fruital-floral odor and bittersweet taste reminiscent of apple.

Occurrence

Reported found in narcissus.

Uses

Cinnamyl formate is used in trace amounts in flavor compositions, particularly Apple, Banana, Cherry,Pear, Spice, etc. It is particularly interesting in imitation Banana, where it can produce true-to-Nature notes if used discretely, and perhaps in combination with Mimosa absolute, also in traces.

Preparation

By esterification of cinnamyl alcohol with formic acid.

Aroma threshold values

Detection at 1.0%: cinnamon spicy, slightly balsamic, cherry fruity with berry and tropical nuances.

Taste threshold values

Taste characteristics at 5 ppm: sweet, cinnamon-like, astringent, with woody resinous and balsamic nuances.

General Description

Cinnamyl formate is an α,β-unsaturated?ester that can be used as a flavoring agent and a fragrance ingredient.

Flammability and Explosibility

Not classified

Safety Profile

Moderately toxic by ingestion. See also ESTERS. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

To a flame-dried flask equipped with a stir bar and activated molecular sieves, IMes-HCl (A1-HCl, 6.8 mg, 0.02 mmol) and toluene (2 mL) were added under an inert atmosphere. A toluene solution of 0.5 M KHMDS (0.04 mL) was slowly added to the stirring suspension with continuous stirring for 15 min. Subsequently, a toluene (2 mL) solution of cinnamyl alcohol (1 mmol) and methyl formate (600 mg, 10 mmol) was added, the flask was sealed, and the reaction was heated for 16 hours at 45 °C. Upon completion of the reaction, the crude product was directly sampled onto a silica gel column for purification, resulting in cinnamyl formate.

Metabolism

Cinnamyl formate is hydrolysed by porcine pancreatic lipase 2.6 times more rapidly than is cinnamyl oleate under identical conditions (Brockerhoff, 1970).

References

[1] Synthesis (Germany), 2017, vol. 49, # 15, p. 3505 - 3510

CINNAMYL FORMATE(104-65-4)Related Product Information

• CINNAMYL FORMATE
• Cinnamyl acetate
• CINNAMYL ISOBUTYRATE
• Cinnamyl cinnamate
• ANTHRANILIC ACID CINNAMYL ESTER
• 3-PHENYLACRYLIC ANHYDRIDE
• 4,6-DIPHENYLTHIENO[3,4-D]-1,3-DIOXOL-2-ONE 5,5-DIOXIDE
• VULPINIC ACID
• 2,3-DIPHENYLMALEIC ANHYDRIDE
• Phenylmaleic anhydride
• FEMA 2302
• Cinnamyl propionate
• FEMA 2296
• PHENYL FORMATE
• 3,4-DIHYDRO-1,2-NAPHTHALENEDICARBOXYLIC ANHYDRIDE
• Pulvinicanhydride
• ALPHA-N-AMYL CINNAMYL ACETATE
• RHIZOCARPIC ACID