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cyclohexyl cinnamate

Cyclohexyl cinnamate is an ester of cinnamic acid known for its fruity aroma and flavor, utilized primarily as a flavor and fragrance agent.

General Material Description

Cyclohexyl cinnamate is a synthetic ester resulting from the combination of cinnamic acid and cyclohexanol, yielding the molecular formula C15H18O2. This compound appears as a clear liquid with scent qualities characterized by fruity, balsamic, cherry, and almond notes, offering a medium-strong odor with substantivity lasting over 60 hours at full concentration. Also known by several synonyms, including cinnamic acid cyclohexyl ester and cyclohexyl 3-phenylprop-2-enoate, it is registered under identifiers such as CAS numbers 7779-17-1 and 138964-30-4. Cyclohexyl cinnamate is accessible through chemical synthesis routes and is a documented entity in authoritative sources like PubChem. Its organoleptic profile makes it valuable in flavor and fragrance sectors.

Occurrence, Applicability & Potential Uses

This ester does not occur naturally in significant quantities but is produced industrially for flavor and fragrance use. Cyclohexyl cinnamate contributes predominantly fruity notes reminiscent of apricot, cherry, peach, and prune, enhancing formulations where such character is desired. It is classified under flavor and fragrance agents and is recognized by FEMA (US) under the number 2352. Regulatory frameworks, including IFRA (Global), permit its use with concentration limits, generally up to 5% in fragrance concentrates. Its suitability for baked goods, frozen dairy, fruit ices, and hard candies reflects its adaptability. The compound provides notable substantivity and olfactory contribution in diverse applications.

Physico-Chemical Properties Summary

Cyclohexyl cinnamate exhibits a moderate molecular weight of approximately 230.3 g/mol and a molecular formula of C15H18O2. It has a logP value near 4.24, indicating considerable lipophilicity, and a specific gravity ranging 1.048 to 1.058 at 25 °C. The refractive index varies between 1.56 and 1.564 at 20 °C. Its boiling point is observed at 139 to 143 °C under reduced pressure (1 mm Hg), signifying volatility under vacuum conditions. The flash point is around 143 °C (290 °F), suggesting stability at typical usage temperatures. Solubility parameters show solubility in alcohols and very limited water solubility (approximately 3.393 mg/L at 25 °C). These properties affect formulation considerations, especially solvent choice and volatility control in flavor and fragrance compositions.

FAQ

What is cyclohexyl cinnamate and what does it smell like?
Cyclohexyl cinnamate is a synthetic ester derived from cinnamic acid and cyclohexanol. It is characterized by a medium-strength fruity odor with balsamic, cherry, peach, and almond nuances. This compound also imparts a similar fruity flavor profile, making it valuable in flavor and fragrance applications.
Where is cyclohexyl cinnamate used and how is it applied?
Cyclohexyl cinnamate is mainly employed as a flavor and fragrance agent in various consumer products. It enhances aromas in items such as baked goods, frozen dairy, fruit ices, and hard candies by contributing apricot, cherry, and prune notes. Its usage levels are controlled to maintain product safety and olfactory balance.
What regulations and safety considerations apply to cyclohexyl cinnamate?
This compound is recognized under FEMA (US) flavoring substance number 2352 and has been evaluated by international bodies such as JECFA. IFRA (Global) guidelines recommend usage not exceeding 5% in fragrance concentrates. Available safety data indicate no significant hazard classifications according to OSHA HCS. Usage levels in food products are established to ensure safe daily intake, with assessments from organizations including EFSA and RIFM.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB37706
FooDB:FDB016834
Export Tariff Code:2916.12.6000

General Material Information

Preferred name cyclohexyl cinnamate
Trivial Name cyclohexyl 3-phenylprop-2-enoate
Short Description cinnamic acid, cyclohexyl ester
Formula C15 H18 O2
CAS Number 7779-17-1
CAS Number 138964-30-4
FEMA Number 2352
Flavis Number 9.744
ECHA Number 231-921-8
FDA UNII Search
Nikkaji Number J326.562E
MDL MFCD00046350
COE Number 337
xLogP3-AA 4.00 (est)
NMR Predictor External link
JECFA Food Flavoring 667 cyclohexyl cinnamate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 7779-17-1 ; CYCLOHEXYL CINNAMATE
Synonyms
  • cinnamic acid cyclohexyl ester
  • cinnamic acid, cyclohexyl ester
  • cyclohexyl 3-phenyl acrylate
  • cyclohexyl 3-phenyl propenoate
  • cyclohexyl 3-phenyl-2-propenoate
  • cyclohexyl 3-phenylacrylate
  • cyclohexyl 3-phenylprop-2-enoate
  • cyclohexyl beta-phenyl acrylate
  • 3-phenyl-2-propenoic acid cyclohexyl ester
  • 2-propenoic acid, 3-phenyl-, cyclohexyl ester

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 230.30685424805
Specific gravity @ 25 °C
Pounds per Gallon 8.72 to 8.804
Refractive Index 1.56 to 1.564 @ 20 °C
Boiling Point 139 to 143°C @ 1 mm Hg
Flash Point TCC Value 143.33 °C TCC
logP (o/w) 4.24
Solubility
alcohol Yes
water, 3.393 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Fruity
fruity, peach, cherry, cherry maraschino cherry, almond bitter almond, cinnamyl
Odor strength medium
Substantivity 63 hour(s) at 100.00 %
Luebke, William tgsc, (2021) At 100.00 %. fruity peach cherry maraschino cherry bitter almond cinnamyl
Flavor Type: Fruity
fruity, balsamic, soapy, cherry, honey, almond, cinnamyl
Luebke, William tgsc, (2021) Fruity balsamic soapy cherry honey almond cinnamyl

Potential Uses

Applications
Odor purposes Apricot , Cherry , Peach , Prune

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for cyclohexyl cinnamate usage levels up to:
5.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.37 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.04 (μg/capita/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 4.0000020.00000
beverages(nonalcoholic): -2.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 1.000005.00000
fruit ices: 1.000005.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 4.0000010.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 15 (FGE.15): Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 55 (FGE.55): Consideration of phenyl-substituted aliphatic alcohols and related aldehydes and esters evaluated by JECFA (63rd meeting) structurally related to phenethyl alcohol, aldehyde, esters and related phenylacetic acid esters evaluated by EFSA in FGE.14 (2005) and aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives evaluated by EFSA in FGE.15 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 15, Revision 1 (FGE.15Rev1) - Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 68 (FGE.68): Consideration of cinnamyl alcohol and related flavouring agents evaluated by JECFA (55th meeting) evaluated by EFSA in FGE.15Rev1 (2008)
View page or View pdf

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EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
National Institute of Allergy and Infectious Diseases:Data
cyclohexyl 3-phenylprop-2-enoate
Chemidplus:0007779171
cyclohexyl (E)-3-phenylprop-2-enoate
Chemidplus:0138964304